Explorez tous les épisodes du podcast Coach2Scale: How Modern Leaders Build A Coaching Culture

After more than 100 episodes, #Coach2Scale wraps with a powerful closing message from host Matt Benelli, one that goes far beyond sales tactics. In this final episode, Matt shares four hard-earned truths from hundreds of conversations with CROs, enablement leaders, and frontline managers. He challenges the myth of the “super rep turned manager,” breaks down the true ROI of coaching (7–8X when done right), and reminds us that one-on-ones aren’t just a task, they’re the operating system for growth.

Matt also reflects on why performance loops aren’t enough without practice loops, and how great teams aren’t built on pressure, but on preparation. This episode connects the dots between personal development and business outcomes; it’s a call for CROs and GTM leaders to stop managing through dashboards and start developing their people with purpose. If you're serious about building a high-performing team that lasts, this episode is your blueprint.

Top Takeaways

1. The human side of coaching is non-negotiable.
Vulnerability-based trust isn’t soft; it’s the foundation for accountability, belief, and long-term performance.

2. Properly equipped managers deliver 7–8X ROI.
Coaching isn’t a “nice to have”; consistent, structured 1:1s lead to higher engagement, lower attrition, and stronger pipeline performance.

3. Stop promoting super reps into management without support.
Selling and coaching are completely different skills; without systems and training, you set managers (and their teams) up to fail.

4. Practice beats performance.
Top teams don’t just execute, they review, adapt, and improve with immediate, behavior-focused feedback that drives lasting change.

5. Coaching isn’t a tool; it’s a behavior change engine.
Technology alone doesn’t drive growth; tying behavior improvement directly to outcomes is what makes a coaching culture truly effective.

6. One-on-ones are not optional; they’re the operating system.
When coaching becomes the standard cadence, it shifts manager behavior from reactive firefighting to proactive development.

7. Performance grows when reps feel developed, not just measured.
The best leaders strike a balance between empathy and accountability, investing in long-term careers rather than just meeting short-term quotas.

8. Coaching is how you scale without breaking your team.
Growth doesn’t come from dashboards or pressure; it comes from developing people who are confident, capable, and aligned.

In this replay episode of Coach to Scale, host Matt Bonelli sits down with Josh Allen, a veteran sales leader from LogMeIn, CarGurus, Drift, and other notable companies, to unpack what it truly takes to elevate sales performance. Together, they explore the myths of sales leadership, why “what worked for you” won’t always work for your team, and how curiosity, drive, and resilience shape top performers. Josh shares hard-earned lessons from building high-performing teams, along with strategies for identifying intrinsic traits during hiring and coaching salespeople with diverse motivations.

Listeners will walk away with practical insights on connecting personal and professional goals, developing consistent coaching rhythms, and sustaining quota attainment without falling into the trap of “growth at all costs.” From nurturing top performers who are often overlooked, to coaching through adversity and building cultures of accountability, this conversation is packed with actionable takeaways for frontline managers, VPs, and anyone passionate about building resilient sales teams.

Top Takeaways

1. What worked for you won’t work for everyone.
Great sales leaders learn quickly that their personal playbook can’t simply be copied and pasted onto their team.

2. Hire for intrinsic traits, train for skills.
Curiosity, drive, and resilience are largely unteachable, whereas sales processes and methodologies can always be refined and developed.

3. Connect personal goals to professional performance.
Helping reps tie career milestones to life goals (like paying off debt or buying a home) builds deeper motivation and accountability.

4. Don’t overlook your top performers.
High achievers also need coaching and career development, not just attention to struggling representatives.

5. Toxic performance is never worth it.
Even the highest producers can’t be allowed to undermine team trust or culture.

6. Coaching is non-negotiable.
Leaders who claim they “don’t have time to coach” are missing the very activity that drives quota attainment.

7. Focus on one change at a time.
Like a golf swing, coaching is most effective when managers help reps improve one skill consistently before moving to the next.

8. Long-term consistency beats short-term intensity.
Sustainable sales success stems from steady development and efficient growth, rather than hiring sprees and short-lived pushes.

In this replay episode of Coach to Scale, host Matt Bonelli sits down with Ben Johnson, VP at Zendesk, seasoned sales leader, and longtime CrossFit coach, to explore what it really takes to build a thriving sales career. Drawing on more than 25 years of experience at companies like Dell, Oracle, Workday, and Zuora, Ben challenges the myth that sales success is measured only by the quarter. Instead, he shares why the true differentiator is consistent coaching, a culture of accountability, and the willingness to sharpen your sword through personal development.

Listeners will walk away with actionable insights on transforming performance improvement plans into coaching opportunities, creating cultures where vulnerability is strength, and distinguishing between “must-dos” and “how-tos” in sales leadership. From rebranding coaching as a growth engine to embracing “deeds, not words,” this conversation delivers timeless lessons for sales reps, managers, and leaders who want to play the long game and win.

Key Takeaways

1. Coach to the career, not the quota – Long-term success comes from developing people beyond just hitting short-term numbers.

2. Performance Improvement Plans can be growth tools – When used correctly, PIPs should guide reps toward improvement, not serve as a punishment.

3. Coachability is the key to success – The most successful reps are those open to feedback, willing to adapt, and eager to learn.

4. Culture starts at the top – A strong coaching culture must be modeled by leadership and reinforced consistently across the organization.

5. Preparation and debriefing matter as much as the meeting – Success comes from doing the pre-work, running the meeting, and reflecting afterward to continually improve.

6. Focus on “must-dos” vs. “how-tos” – Clear expectations around the basics (like CRM hygiene) free up time to coach on higher-value selling skills.

7. Deeds, not words – Accountability is proven through consistent actions, not promises.

8. Get the bad news early – Addressing risks and challenges upfront allows teams to respond effectively instead of scrambling at the last minute.

9. Invest in personal development – Ongoing learning, mentorship, and self-improvement are essential to staying sharp and thriving in sales.

10. Find mentors and be one – Having someone to guide you (and paying it forward to others) accelerates growth and resilience in a sales career.

In this episode of Coach2Scale, author, professor, and board advisor Rachel Pacheco joins host Matt Bonelli to unpack one of the most overlooked drivers of sales performance: meaning. Drawing from her research and experience working with fast-scaling startups and MBA students alike, Rachel challenges the myth that salespeople are only motivated by money or perks. Instead, she shows why helping reps find purpose in their day-to-day work leads to deeper engagement, higher productivity, and better retention, and why frontline managers have the greatest influence over that outcome.

You’ll hear practical ways to coach for meaning, how to deliver feedback that builds self-awareness and performance, and why micromanagement isn’t the real problem, meaninglessness is. Rachel shares coaching tactics for time-strapped managers, explains the risks of cookie-cutter motivation strategies, and outlines how structured 1:1s can become high-trust development conversations. Whether you're a CRO, frontline manager, or enablement leader, this episode will help you rethink how to build a culture where performance and purpose go hand-in-hand.

Key Takeaways

1. Meaning is a daily experience, not a grand purpose.
Most employees aren't searching for their “life’s purpose” at work; they’re looking for day-to-day meaning in their tasks, interactions, and progress.

2. Managers play a central role in helping reps find meaning.
It's a myth that meaning is personal and out of a manager’s scope; the way managers structure work, give feedback, and coach reps directly influences how meaningful their work feels.

3. Productivity increases when reps experience more meaning.
Research, including studies by Adam Grant, shows that employees who understand the why behind their work are not only more engaged but also more productive and resilient.

4. Motivation is personal and needs to be customized.
Not all reps are driven by competition or money; some value connection, stability, or mastery, and managers must learn what uniquely drives each individual.

5. Great coaching starts with structured autonomy.
Managers should set clear expectations and outcomes, then give reps the space to figure out the “how”; this autonomy fosters ownership, trust, and greater meaning.

6. Effective feedback is specific, timely, and impact-driven.
Generic praise (“Great job!”) is forgettable; meaningful feedback highlights what was done well, why it mattered, and how it helped the team or business.

7. Constructive feedback is a growth opportunity, not a threat.
Most employees want more feedback, even the tough kind, but managers often avoid it due to discomfort, missing critical chances to drive behavior change.

8. Curiosity is a manager’s superpower.
Asking thoughtful questions helps uncover what motivates each rep, what’s holding them back, and how to connect daily work to a more profound sense of purpose.

9. Coaching isn’t about giving answers; it’s about guiding reflection.
Coaching helps reps build self-awareness, clarify decisions, and reflect on their growth; it’s less about solving problems and more about building capability.

10. Don’t wait for better managers; teach your current ones how to coach.
Many frontline managers were promoted without training; they don’t lack intent, they lack tools. Organizations must invest in teaching them how to lead through coaching.

In this episode, Sean Harvey, CRO at RocketRez, shares a practical framework for building coaching cultures that actually stick. He explains why trust, not tactics, is the starting point for real performance, and how coaching must move beyond pipeline reviews and into intentional skill development. From his early Oracle training to leading teams through hypergrowth and private equity scale-ups, Sean outlines the lessons that shaped his belief in coaching as both a performance lever and a retention strategy.

If you’re still coaching “on the fly” or stuck playing super-rep, this conversation will challenge your assumptions. Sean covers the link between psychological safety and rep engagement, how vulnerability-based trust unlocks real development, and why sustainable growth demands coaching at every level from C-suite to the frontlines. You’ll walk away with a clearer understanding of what coaching is, what it’s not, and how to build a team that stays, grows, and performs.

Key Takeaways

1. Coaching must start at the top to stick long-term
If the C-suite doesn’t model and prioritize coaching, it gets deprioritized the moment short-term pressure hits.

2. Trust is the foundation of any real coaching culture
Reps won't grow unless they believe their manager has their long-term development, not just this quarter’s numbers, in mind.

3. Vulnerability-based trust drives engagement and learning.
Creating psychologically safe spaces where reps can fail and learn openly is what unlocks real skill development.

4. Great managers coach people, not just deals.
Coaching isn’t about saving deals; it’s about building reps who can consistently win without constant intervention.

5. Consistency matters more than intensity.
A lightweight but regular coaching rhythm beats sporadic “inspiration bursts” that vanish under pressure.

6. You can’t scale if you’re only hiring more reps.
Scalability means increasing productivity per rep, which only happens when you build coaching into the operating system.

7. Coaching drives retention, especially in high-talent environments
Reps stay where they feel invested in, especially when they’re being challenged to grow with structure and support.

8. Managers are overwhelmed and under-equipped to coach
Most FLMs were promoted as top reps but were never taught how to develop others; tools and frameworks help close this gap.

9. The best leaders have coaching “trees”
Just like in sports, great coaches produce other great coaches; mentoring others to lead is a force multiplier.

10. Success is compounding when coaching becomes culture
When coaching becomes normalized, teams get better, faster, improving not just results, but predictability.

In this special episode of Coach to Scale, host Matt Benelli takes on a bold challenge: a live cold-call role play with Hyperbound’s AI-powered prospecting bot one of the “rudest bots on the planet.” Joined by Hyperbound co-founder and CEO Sriharsha Guduguntla, Matt puts his skills to the test, showcasing how sales reps can practice real-world scenarios, handle objections, and refine their pitch with real-time coaching. The result? A raw, unfiltered look at what happens when the pressure is on and every word counts.

Listeners will walk away with insights into effective prospecting, the power of permission-based openers, handling resistance with confidence, and how instant AI feedback can accelerate coaching and skill development. Whether you’re a sales leader, manager, or rep looking to sharpen your edge, this episode delivers a front-row seat to practical techniques, lessons learned, and a clear takeaway: you don’t have to love cold calling you just need to practice, improve, and get better every time.

Key Takeaways

1. Practice under pressure matters – Putting yourself in tough role plays with AI bots helps reps simulate real-world challenges and improve faster than passive learning.

2. Instant feedback accelerates growth – AI delivers coaching in real time with detailed scoring criteria, so reps don’t have to wait for a manager’s one-on-one to learn what to improve.

3. Consistency beats comfort – You don’t need to love cold calling, but consistent practice builds confidence and competence over time

4. Three types of prospectors – Some salespeople thrive on cold calls, some avoid them but claim they do, and managers often love them because they don’t have to make them anymore, recognizing this helps leaders coach more effectively

5. Objection handling is a teachable skill – With structured practice and coaching, reps can learn to confidently navigate push back and still secure meetings

6. AI empowers both reps and managers – By offloading repetitive role plays and providing objective coaching, managers can spend more time on strategy while reps still get valuable development.

7. Anyone can try it – Hyperbound makes its prospecting bots publicly available so sales professionals can test themselves, practice as often as they want, and benchmark improvement

Scaling teams inside matrixed organizations is rarely about speed alone. Shane Hughes, Head of Customer Success at LinkedIn and former Salesforce executive, argues that real growth comes from slowing down to coach with intention, aligning stakeholders early, and focusing relentlessly on customer value. In this conversation, he shares how leaders can avoid the trap of “chasing renewals” and instead build advocacy from the start by connecting adoption to measurable business outcomes.

Shane also pulls from his experience leading teams that grew revenue from millions to billions to highlight what separates managers from true coaches. He explains why curiosity is the foundation of influence, how consistency compounds impact, and why high performers act more like consultants than communicators. Whether you’re a CRO, frontline manager, or rep aiming to lead, his lessons offer a clear path to scaling without losing your edge.

Key Takeaways

1. Renewals are won early, not saved late – Retention isn’t about heroics at the end of a contract; it’s about shaping value in the first months after a deal closes.

2. Adoption does not equal value – Usage is necessary but meaningless unless it connects to the customer’s defined business outcomes.

3. Curiosity drives advocacy – The best customer success leaders don’t just communicate; they ask sharp questions that reframe problems and uncover hidden opportunities.

4. Coaching beats chasing – Managers who focus on coaching their teams to think like consultants create consistent impact, while those who chase activity confuse motion with progress.

5. Slow down to speed up – Scaling in matrixed organizations requires alignment and influence across stakeholders; patient lobbying accelerates outcomes later.

6. Consistency compounds – Small, repeatable practices in coaching and customer engagement build long-term trust and measurable growth.

7. Leaders must coach across, not just down – True leadership requires influencing peers and executives in addition to managing direct reports.

Too many frontline managers are promoted for hitting quota, then left to figure out leadership on their own. In this episode, Jeff Cummings, COO at LLC Attorney, shares a battle-tested coaching playbook built through 20+ years of leading high-growth teams. He challenges the “leadership lie” that there's no time for 1:1s and lays out a structured, repeatable framework that transforms one-on-ones from status updates into high-impact coaching sessions.

Jeff walks through how to coach top performers without coddling them, how to use AI to scale personalized development, and why being a good manager has nothing to do with being in the deals. This episode is packed with practical guidance for CROs, RevOps, and enablement leaders looking to build durable revenue teams, starting with better coaching habits at the frontline.

Key Takeaways

1. The “Leadership Lie” is that there's no time for 1:1s.
Jeff calls out the myth that leaders are too busy to coach; if you're too busy for your people, you're too busy to lead.

2. One-on-ones should be structured, consistent, and focused on development, not deals.
Effective 1:1s follow a repeatable process that goes beyond pipeline reviews to drive skill growth and accountability.

3. Coaching should start with reflection by the rep.
Asking “what went well?” first gives the rep ownership and builds a coaching culture grounded in self-awareness.

4. Top performers need coaching, too, especially around behavior and professionalism.
Being a high producer doesn’t exempt someone from expectations; true leaders help reps round out their game.

5. Managers must separate being in the action from building the team that drives the action.
If you're still acting like a super rep, you're not creating leverage, and you're stunting team growth.

6. Missed 1:1s should be rescheduled immediately, not skipped.
Treat coaching like a customer meeting; canceling without rescheduling signals that people aren’t the priority.

7. AI can be used to scale coaching, not replace it.
Jeff uses AI to track commitments, organize feedback, and personalize development, but the human connection stays central.

8. Be fully present, no Slack, no inbox, no distractions.
Undivided attention during coaching moments signals to reps that their development matters.

9. Coaching isn’t a task; it’s a leadership mindset.
Great leaders don’t wait for permission to coach or train; they take ownership of their team’s growth trajectory.

10. Pay mentorship forward, build a legacy through people.
Jeff credits his early mentors and reinforces that the best ROI in leadership comes from investing in others and teaching them to do the same.

LinkedIn profile: https://www.linkedin.com/in/jeffcummings/

In this episode of Coach to Scale, we sit down with Sriharsha "Sai" Guduguntla, co-founder of Hyperbound, to unpack one of the most pressing challenges in revenue leadership: the coaching crisis. Despite billions invested in enablement tools, most frontline managers still spend less than 5% of their time actually coaching, and it's costing teams deals, confidence, and retention. Sai shares how Hyperbound is redefining sales practice by enabling reps to roleplay high-stakes calls, objections, and negotiations using AI before they ever speak to a real prospect.

Sai and host Matt Benelli explore why traditional training doesn’t stick, how to coach the iPhone generation, and why AI-driven feedback is the key to scalable performance improvement. From building reps’ confidence to reducing CAC, shortening ramp time, and even coaching managers themselves, this conversation delivers practical insight for CROs and GTM leaders committed to leveling up their teams. If you think having Gong means you’re coaching, think again.

Key Takeaways

1. Coaching is broken, and leaders know it.
Most frontline managers spend less than 5% of their time coaching, and even if they admit it's not enough, despite having tools like Gong or Chorus.

2. Owning tools doesn’t mean using them.
Just because you’ve bought sales tech doesn’t mean your team is getting value from it; usage and enablement are two different things.

3. Reps are practicing on real prospects, and that’s a problem.
Without structured practice environments, reps learn in live selling situations, losing deals and confidence in the process.

4. AI enables real, scalable practice.
Hyperbound uses AI to let reps roleplay discovery, objections, and negotiations with instant feedback, so they improve before going live.

5. Training decay is real 87% is forgotten in a month.
Sai shares how Hyperbound clients are replacing costly SKOs and one-off trainings with ongoing practice that reinforces key skills year-round.

6. Feedback should be immediate, not delayed.
Instead of waiting weeks for one-on-one feedback, reps using AI tools can instantly iterate and refine their performance after each session.

7. AI coaching is objective and data-backed.
AI removes bias by evaluating reps consistently, benchmarking them against top performers, and identifying real improvement areas.

8. Confidence is often the root blocker to performance.
A lack of confidence, not skill, is what holds many reps back from picking up the phone; Hyperbound helps reps build that confidence safely.

9. Managers need coaching too.
Hyperbound doesn’t just coach reps, it also trains managers by simulating coaching conversations and giving feedback on their effectiveness.

10. Culture matters more than tools.
Without leadership buy-in and a true coaching culture, even the best tools won’t lead to behavior change; some orgs just aren’t ready.

What happens when a top-performing rep becomes a people-first leader in one of the most demanding roles in tech? In this episode of Coach2Scale, Jeff Perry, CRO at Carta, shares his leadership journey from his early days at Oracle to building high-performing, diverse teams at Carta. He unpacks the misconceptions that still hold sales leaders back, like the idea that only hard-charging, deal-focused managers succeed, or that considerable company experience doesn't translate to startup growth. Jeff challenges these myths with candor, offering lessons for anyone navigating their evolution as a leader.

The conversation tackles why being a “nice leader” isn’t a liability, how to hire from non-obvious backgrounds, and why no one should ever lose a deal alone. Matt and Jeff also dig into the most challenging job in sales, the frontline manager, and why equipping them with the right mindset and tools is the only way to scale performance sustainably. Whether you're a rep, manager, or CRO, this episode will help you rethink how leadership, culture, and coaching intersect to drive lasting results.

Key Takeaways

1. Lean into who you are as a leader
Stop trying to fit someone else’s mold, own your style, values, and story to build authentic credibility.

2. Prominent company leaders can thrive in startups.
Success in enterprise sales doesn’t disqualify you from excelling in high-growth, early-stage environments if you can translate your experience.

3. Empathy and accountability are not mutually exclusive
Being a “nice” leader doesn’t mean being soft; it means building trust so you can challenge and develop your people effectively.

4. Hiring for diversity improves team performance.
Creating teams with varied backgrounds and experiences, not just résumés, leads to more resilience, learning, and results.

5. Balanced team performance is more sustainable than star-centric models
Hitting 115% with everyone contributing beats 130% with a few carrying the load, especially when building culture and scale.

7. Managers should never lose a deal alone.
The best AEs use the entire team, from executives to product, to win; lone-wolf selling is inefficient and risky.

8. Coaching should focus beyond the deal.
Too many 1:1s revolve around the pipeline; great leaders use coaching to build reps’ long-term skills and confidence.

9. Sales leadership is about consistency through volatility
In unpredictable markets, reps need leaders who are steady, transparent, and focused on what can be controlled.

10. High growth creates opportunity, but only for those who embrace it
Carta’s rapid evolution has opened new career paths, but leaders must stay close to the people and remain hands-on to unlock them.

11. Frontline managers need structure and support to succeed
The FLM role is the most overloaded in the org; without tools, coaching frameworks, and clarity, they default to dealing with triage and burnout.

Consistency beats charisma in frontline sales leadership. In this episode of Coach2Scale, VMware Carbon Black’s Head of Sales Development, Victoria Abeling, shared what it takes to build a high-performance team when everyone’s overworked and every 1:1 is at risk of being replaced by a pipeline review. She unpacks why many reps view coaching as punitive, how that culture was unintentionally built over decades, and the mindset shift required to make coaching a trusted, productive habit, not a compliance exercise.

Victoria offers a pragmatic breakdown of how she uses quarterly operating cadences, individualized development plans, and coaching conversations grounded in deal inspection to uncover skill gaps, not just red flags. You'll hear how to coach for discovery, disqualify with confidence, and push back on the myth that high performers don’t need help. If you're a sales leader tired of playing firefighter, or a CRO wondering why the pipeline isn't growing with headcount, this conversation will reframe how you think about performance management and the role cadence plays in building trust, accountability, and results.

Top Takeaways

1. Coaching is not punitive; it’s a performance multiplier.
Many reps assume coaching signals underperformance, but reframing it as a skill-development tool builds trust and accountability.

2. Consistency in 1:1s is non-negotiable.
Coaching only drives behavior change when it follows a predictable cadence; skipping sessions sends the message that development is optional.

3. Top performers need coaching too.
Even the best reps have blind spots, and coaching them to sharpen specific skills is how you go from 100% to 130% of quota.

4. Quarterly operating rhythms help leaders avoid reactive management.
Structuring the year into coaching and development cycles keeps leaders proactive, not just in-the-weeds on deals.

5. Coaching must go beyond the deal to address the “how,” not just the “what.”
Managers who only review pipelines miss opportunities to build long-term skills like discovery, negotiation, and qualification.

6. Disqualification is as valuable as closing.
Teaching reps to say “no” to the wrong opportunities frees them to invest time in the right ones and protects forecast accuracy.

7. Modern buyers are informed; sellers must be sharper in discovery.
With buyers doing most of the research on their own, reps must master early discovery to stay relevant and competitive.

8. Leaders must learn to receive feedback without defensiveness.
Victoria shares how this mindset shift helped her grow as a leader and foster stronger coaching relationships.

9. How you show up matters, even on Zoom.
From attire to preparation, professionalism in remote settings still signals credibility and respect.

10. Coach the individual, not the scoreboard.
Coaching should focus on skills that compound over time, not just pressing for this month’s number.

Matt Benelli sat down with Mark Roberge last year, former CRO at HubSpot, Harvard Business School professor, and co-founder of Stage 2 Capital, to challenge some of the most persistent myths in sales leadership. From debunking the idea that top reps make the best managers to exposing why shadowing high performers can actually backfire, this conversation delivers a candid look at why most coaching programs fail to scale and what to do instead.

Mark lays out a structured, repeatable approach to frontline coaching that not only boosts individual rep performance but transforms how entire sales organizations operate. He shares why focusing on team attainment is less useful than tracking the percentage of reps hitting quota, how managers can move from reactive fire drills to proactive coaching cycles, and why self-diagnosis is the new sales superpower. If you're a sales leader still stuck on the hamster wheel, this episode offers a way off.

Key Takeaways

1. Top reps don't make the best managers
The traits that drive individual quota success, such as assertiveness or autonomy, often conflict with the empathy and patience required to coach others effectively.

2. Shadowing high performers is not an onboarding strategy
New reps pick up bad habits and unteachable skills when learning only by imitation; structured onboarding with a defined process is more effective.

3. Coaching can (and must) scale.
A consistent, top-down cadence of rep-by-rep skill diagnosis, action planning, and metric tracking creates scalable coaching across large sales orgs.

4. Reps rarely know why they’re underperforming
Without data, reps and managers often misdiagnose performance gaps; combining call data and funnel metrics helps uncover the true root causes.

5. Managers must move from reactive to proactive
Time-blocked 1:1s tied to skill development, not just deal triage shift coaching from “fire drills” to intentional growth plans.

6. Quota attainment by rep is the real health metric.
Overall team attainment hides unhealthy reliance on a few stars; the percentage of reps hitting quota shows true team performance and scalability.

In this episode of Coach2Scale, CoachEm CEO and co-founder Colum Lundt joins host Matt Benelli to unpack a critical but often overlooked reality in sales leadership: frontline managers are the linchpin to scalable growth, yet they’re routinely undertrained, overwhelmed, and underleveraged. Colum shares firsthand insights on why simply promoting great reps into management roles isn’t working and how the right tools, data, and AI-powered systems can transform managers from reactive deal chasers into proactive skill builders.

Listeners will walk away with a clearer understanding of how AI should act as a copilot, not a crutch; the compounding impact of consistent developmental coaching over deal coaching; and how to drive real behavior change in reps without adding more to a manager’s plate. If you’re a CRO thinking about enablement, productivity, and long-term performance, this episode offers a sharp, no-nonsense look at what’s broken and what you can do to fix it.

Key Takeaway

1. Frontline Managers Are the Most Underdeveloped Yet Most Critical Role in Sales
Managers get the least training and the most pressure, yet their influence has the highest ROI, up to 7–8x for every dollar invested.

2. AI Should Be a Copilot, Not a Replacement
The future of sales management lies in AI that augments human leadership by handling prep, surfacing insights, and reducing cognitive overload, not replacing empathy and accountability.

3. Developmental Coaching Is What Scales, Not Deal Coaching
Skills coaching “between the games” has far more long-term value than reactive deal coaching, which often reinforces short-term thinking.

4. Manager Span of Control Has Exploded
The average frontline manager is managing too many reps with too many tools and no time to coach; CoachEm helps them scale themselves without sacrificing quality.

5. Change Fatigue and Tech Overload Are Crushing Sales Teams
Especially in mid-market, reps and managers are drowning in tools and new initiatives without a clear structure or prioritization, which undermines focus and execution.

6. AI-Powered Role Play Is a Breakthrough for Enablement at Scale
CoachEm’s integration with Hyperbound lets companies simulate real conversations—both for reps and for managers dramatically improving readiness without needing live trainers.

7. CoachEm Makes Performance Coaching Measurable and Repeatable
The platform uses CRM, call transcripts, and behavioral data to show exactly what’s working and what’s not, down to missed calendar invites that slow deal velocity.

8. The Best Reps Still Need Coaching, They Need Different Coaching
Even top performers benefit from sharpening specific skills; the right system gives managers the data to coach everyone, not just the squeaky wheels.

9. Customer Success Is the Next Frontier for Coaching Execution
As more CSMs are pulled into revenue roles, CoachEm is expanding to support upsell, cross-sell, and relationship-building motions as rigorously as sales.

10. If You Want to Fix Sales Productivity, Start by Fixing the Manager Experience
Sales cultures that prioritize manager development first see better rep retention, stronger pipelines, and more consistent execution across teams.

Welcome to Episode 100 of the Coach2Scale Podcast! In this milestone edition, host Matt Benelli delivers a no-nonsense Q2 debrief packed with hard-earned lessons, powerful guest stories, and leadership truths that cut through the noise. From blind spots that sink careers to the non-negotiables of trust, culture, and coaching, this episode distills what it really takes to scale teams and drive meaningful results. Hear firsthand from Kevin McCarthy on self-inflicted downfall, from John Walston on building mental resilience, and from Neil Wood on solving, not selling, your way to a billion-dollar success.

This episode is more than a recap; it’s a call to action. Matt shares five brutally honest themes that every sales leader, coach, and executive needs to hear: coaching is about asking questions, not issuing commands; culture is defined by what you tolerate, not what you say; inconsistency erodes trust; and enablement isn’t optional; it’s your competitive edge. Whether you're leading a team or trying to level up, this episode will challenge your assumptions and light a fire under your Q3 game plan. Let’s get after it, and as always, CoachEm if you want to keep ‘em.

Key Takeaways

1. Adversity Doesn’t Build Character; It Exposes It
2. Stop Pitching. Start Solving. Or Step Aside.
3. Coaching Is a Skill; And Most Managers Suck At It
4. Culture Isn’t a Slogan; It’s What You Tolerate

Guests
1. Kevin McCarthy -  https://www.linkedin.com/in/kevinmccarthycsp/
2. John Walston- https://www.linkedin.com/in/john-walston-63a042206/
3. Neil Wood -  ⁨https://www.linkedin.com/in/neilwoodconsulting/
4. Michael Muhlfelder -  https://www.linkedin.com/in/mikemuhlfelder/
5. Tom Young - https://www.linkedin.com/in/tom-young-7aba11/
6. Mike Montague -  https://www.linkedin.com/in/mikedmontague/
7. Jeff Keplar - https://www.linkedin.com/in/jeffrey-keplar-63a2b86/
8. Mark Kosoglow - https://www.linkedin.com/in/mkosoglow/
9. Kevin Gaither -  ⁨https://www.linkedin.com/in/kevingaither/
10. Tony Burnside - https://www.linkedin.com/in/tonyburnside/
11. Pam Dake - https://www.linkedin.com/in/pamela-dake-1152483/

What happens when a founder-led sales strategy hits its limits? In this episode of Coach to Scale, Ken Grasso, veteran CRO, advisor, and founder of Catalyst Peak Ventures, pulls back the curtain on the messy, mission-critical transition from instinct-driven selling to structured, scalable revenue operations. With experience leading global go-to-market teams and helping companies grow from zero to IPO, Ken shares unfiltered insights on why founders often struggle to let go of sales, the costly myth of the “natural-born” sales leader, and how process, not personality, is the real growth engine.

Packed with real talk for CROs, revenue leaders, and founders alike, this conversation explores the pivotal role of coaching cultures, how to hire for system-fit over resume flash, and the urgent need to professionalize sales before seeking investment or exit. You’ll also hear Ken’s candid reflections on career reinvention, building credibility as a fractional exec, and why planning for the next chapter before you need to is essential for long-term impact. Whether you’re scaling your first team or rethinking what makes sales truly sustainable, this episode is a playbook in disguise.

Top Takeaways

1. Founder-led selling becomes a liability as you scale
Early-stage founders may be the best sellers at first, but their instinctive, unstructured style can block repeatability and growth.

2. Great sales reps don’t automatically make great managers
Promoting top performers without leadership skills or process discipline can stall team performance and create chaos.

3. The sales process is the foundation, not a nice-to-have
A defined, teachable sales process enables forecastable growth, efficient onboarding, and higher valuations.

4. CROs must earn trust and re-educate founders on go-to-market
Transitioning founder-led orgs to scalable operations requires a blend of credibility, patience, and strategic coaching.

5. Hiring should prioritize system-fit and coachability.
The best candidates align with your GTM model and are eager to operate within a defined system, not just shine as individual contributors.

6. You can’t outrun a broken foundation with short-term wins
Heroics might save a quarter, but without an operational structure, you’ll eventually burn out or break the model.

7. Fractional leadership can unlock massive value for growth-stage teams
Bringing in experienced operators part-time can help companies avoid costly misfires and build maturity without overextending budgets.

8. Plan your career pivot before the market makes you do it
Ken urges seasoned leaders to proactively define their “Plan B,” emphasizing personal reinvention and long-term career resilience.

9. Strong systems beat star power—ask the NFL.
Drawing on sports analogies, Ken explains why team performance relies more on consistent playbooks than flashy individuals.

10. Valuation depends on your GTM maturity.
Investors and acquirers don’t just buy your product they buy your ability to sell it repeatedly, predictably, and without founder involvement

What happens when your top-performing rep becomes a struggling front-line manager? In this episode, Dan Freund, Chief Sales Officer at Invoice Cloud and former Oracle sales leader, unpacks the leadership gap plaguing high-growth sales orgs. From rethinking territory design to balancing equity with accountability, Dan shares how he transformed underperforming teams into consistent winners, without clinging to sales superstars or status quo assumptions.

This episode offers a candid look at the hard decisions CROs and sales leaders must make to scale performance without sacrificing culture. You'll hear why conviction matters more than consensus, how to spot reps ready for more than just promotion, and why internal networks can fast-track productivity. If you’re tired of recycling the same top 10% and ready to build a coaching culture where every position matters, this conversation will shift how you lead.

Top Takeaways

1. Don't fear reassigning key accounts.
Even top performers can adapt; keeping all the best accounts with senior reps creates a revolving door for new hires and stalls team growth.

2. Break the “greenfield trap” for new reps.
Reps in undeveloped territories often fail not from lack of talent, but from poor territory design and lack of enablement.

3. Promotion isn’t leadership readiness.
Great reps often struggle as managers unless they’re taught how to coach, hold people accountable, and operate strategically.

4. Coaching must go beyond deal reviews.
Most managers default to pipeline triage; real coaching means developing skills that affect every deal, not just the current quarter.

5. Internal networks matter as much as external ones.
High-performing reps build relationships across legal, finance, and other internal teams early, compressing ramp time and increasing deal velocity.

6. The best leaders make ideas that help the business, not themselves.
Dan’s biggest promotions came from pitching business-first ideas with no personal gain attached; conviction creates opportunity.

7. Equitable territories create stronger teams.
Giving everyone a real shot at success, rather than over-rewarding tenure, builds momentum and reduces attrition.

8. Friendship and accountability can coexist.
Strong relationships within the team don’t weaken performance; they create the trust needed for tough conversations and high standards.

9. Ask: Are you making the news or reporting it?
Reps who lead the sales process proactively outperform those who simply react to buyer-driven next steps.

10. You can build momentum and hit the number.
It’s not either-or; with the right structure, you can build long-term capability while executing in the short term.

When sales targets are missed, most leaders look at the pipeline, process, or personnel. But what if the real issue is a lack of psychological safety? In this episode of Coach to Scale, host Matt Benelli sits down with John Walston, author, entrepreneur, and founder of the Keep On Movement, to explore how vulnerability, empathy, and consistency in leadership can transform sales outcomes. Walston shares how personal adversity reshaped his leadership style, making him a more effective coach and culture builder.

This episode is a must-listen for CROs, VPs of Sales, and frontline managers navigating burnout, underperformance, or high turnover. You’ll walk away with tactical ways to shift from transactional management to human-centered leadership, without sacrificing accountability. Topics include managing anxiety in high-pressure environments, turning 1:1s into developmental moments, and why “get over it” is the fastest way to lose trust and performance. If you lead teams, this conversation will challenge how you measure success and show how culture is a quota strategy.

Takeaways 
1. “Just stop it” doesn’t work, especially in sales leadership.
Telling someone to push through stress or anxiety without support not only fails, but it also damages trust and culture.

2. You can’t lead people effectively if you don’t understand what they’re carrying.
Empathy isn’t a soft skill; it’s a leadership multiplier that directly impacts motivation and consistency.

3. Physical movement drives mental clarity and performance.
Exercise helped Walston recover from a personal crisis, and research shows it’s as effective as medication for many mental health issues.

4. Positivity isn’t the same as being happy.
Leaders can model resilience by moving forward with optimism, even while acknowledging discomfort or hardship.

5. Your team won’t grow if your 1:1s are just pipeline inspections.
Coaching conversations should go beyond deal reviews to include skill development and personal connection.

6. Culture is built in the moments between numbers.
Asking your reps about their weekend and remembering what they said builds trust that translates into accountability.

7. Positive self-talk is a skill leaders must model and teach.
Verbalizing functional thoughts (especially out loud) has a 10x psychological effect compared to internal dialogue.

8. Gratitude changes how you lead and how people follow.
Being grateful for struggle, not just outcomes, shifts the mindset and allows leaders to better support their teams.

9. Even one moment of connection can shift someone’s trajectory.
Whether it’s a smile, a T-shirt slogan, or a question at the right time, leaders have the power to influence more than they realize.

10. “Easy is not best,” and your reps need to hear that.
High standards, not hand-holding, are what help people rise. But they must be delivered with belief and support.

Can Sales Managers Be Friends with Their Reps? The Ultimate Sales Leadership Debate

Should leaders be friendly or firm? In this epic live debate from CoachEm’s inaugural Closing Arguments series, two powerhouse sales veterans, Mark Kosoglow (Co-founder & CEO at Operator, former Outreach leader) and Kevin "KG" Gaither (CEO of InsideSalesExpert.com, former ZipRecruiter exec), go head-to-head on one of the most controversial questions in sales leadership:

“Can, should, or would you be friends with your sales reps?”

Moderated by Matt Benelli, host of the Coach to Scale podcast, this unscripted, no-holds-barred session dives into real stories, polarizing philosophies, and battle-tested experiences on the fine line between empathy and authority.

What you'll learn:

When friendship enhances performance, and when it kills accountability

Why sales managers struggle with tough conversations

The hidden career risks of blurred boundaries

How modern leaders navigate connection, trust, and coaching culture

Get actionable takeaways for building high-performing sales teams while balancing trust, professionalism, and results.

This is not your average webinar. It’s honest. It’s engaging. It’s real sales talk for real sales leaders.

Sponsored by CoachEm: The world’s first AI coaching execution platform, built to scale sales success through data, coaching, and culture.

COMMENT below: Can you be friends with your reps? Where do YOU draw the line?

📥 Subscribe to the Coach to Scale podcast and never miss a real-world sales leadership discussion.

What happens when your strongest reps stop getting better? In this episode of Coach2Scale, Julie Fox, Global Director of Customer Success at Cin7, shares how she transformed "steady but stuck" team members into high-impact players. From busting the myth of one-size-fits-all sales training to implementing a radical feedback culture, Julie unpacks how coaching isn't just for underperformers. It’s a strategic growth engine for the whole team. She explains how her approach to structured, personalized coaching drives not just rep development but cross-functional alignment and executive trust.

Julie also dives into the frontline manager dilemma: they’re overwhelmed, under-supported, and often promoted without the tools to coach effectively. She offers actionable frameworks for feedback that sticks, one-on-ones that matter, and why even your top performers still need direction. Whether you’re a CRO trying to stabilize performance or a new manager navigating the leap from IC to leader, this episode delivers tactical guidance grounded in experience, not theory.

Top Takeaways 

• Generic sales training fails high-context teams.
  Off-the-shelf training doesn’t stick when sales cycles are complex, technical, or regulated; coaching must be personalized to the rep’s world.
• Radical candor beats performance reviews.
  Feedback should be frequent, specific, and kind, not saved for annual reviews or buried in vague praise.
• High performers plateau without stretch coaching.
  Even your best reps need friction to grow; without it, they stagnate and disengage quietly.
• Effective 1:1s start with knowing the rep as a person.
  Understanding motivations, feedback styles, and personal goals unlocks performance in ways dashboards never will.
• Coaching isn't a calendar event; it’s a culture.
  Building feedback loops into day-to-day operations (like peer call reviews and structured office hours) creates sustained behavior change.
• Not all reps are ready for feedback in the same way.
  Great managers check in before delivering feedback to ensure the timing and delivery fit how each rep processes input.
• Manager consistency separates good teams from great ones.
  Sporadic coaching drives uneven results; systematized coaching practices help managers scale development across the team.
• First-line managers need coaching too.
  Most FLMs were promoted without being taught how to lead; equipping them is the fastest way to impact rep performance and retention.
• Team-first leaders earn executive trust.
  Julie’s “Team Number One” mindset shows how customer success leaders can earn CRO alignment by focusing on business outcomes, not just function-specific wins.
• Customer centricity must be operationalized.
  Declaring CS as a priority isn’t enough; Julie made it real by embedding it into cross-functional KPIs and role-specific accountability.

Jeff Keplar, former sales executive at Oracle, MapR, and Google, joins Coach2Scale to challenge one of today’s loudest narratives in SaaS: that product-led growth has made traditional selling obsolete. In this candid, no-nonsense conversation with Matt Benelli, Jeff lays out why complex, high-stakes enterprise deals still demand skilled sellers, strong managers, and real leadership in the field, not just slick UX and freemium funnels. He explains why sales-led growth is often poorly executed, not outdated, and how the caricature of the “golf-playing rep” is holding companies back from serious revenue performance.

This episode is a must-listen for CROs, VPs, and FLMs navigating the blurred lines between coaching, leadership, and execution. Jeff unpacks what makes a sales leader worth following, why frontline managers often fail (and how to fix it), and how real coaching, not just pipeline reviews, builds resilient teams. From scaling at Oracle to advising modern startups, Jeff shares lessons that cut through the noise and help leaders build teams that win the right way.

Key Takeaways 
1. Leadership isn’t granted by title, it’s earned in the field
Sales managers gain real influence by showing up with their team, facing the same pressure, and modeling accountability, not by hiding behind their job title.

2. Sales-led growth isn’t outdated, it’s just misunderstood.
Many critics confuse poor execution with obsolescence; in reality, complex sales still require human insight, coaching, and influence that product-led strategies alone can’t deliver.

3. Stop promoting 'super reps' and expecting them to be great managers
The skill set that drives individual performance often lacks what’s needed to coach, develop, and retain a team, especially in high-growth or enterprise contexts.

4. Great sales leaders don’t kiss up and kick down, they build teams that follow them anywhere
The mark of strong leadership is not upward politics but whether former team members would choose to work with you again.

5. Salespeople need coaching beyond the deal.
Too many 1:1s are just pipeline checks; true coaching focuses on skills, behaviors, and long-term development that compound over time.

6. In enterprise sales, the product doesn’t close the deal; people do
Unlike self-serve SaaS tools, enterprise software buyers need trust, consultation, and risk mitigation that only a well-prepared rep can deliver.

7. When reps are treated like resources, they leave
High attrition often traces back to poor or absent development; reps stay when they feel seen, supported, and challenged.

8. Managers must be the rep’s advocate, even when it costs political capital
Defending your team when it's hard is the kind of leadership people remember and rally around, especially in performance management decisions.

9. Friendship and leadership aren’t mutually exclusive.
While being “one of the crew” can backfire, relationships built on trust and mutual respect lead to better coaching conversations and loyalty.

10. Coaching is influence, not control.
The goal is to shape behavior through insight and conversation, not compliance, which is also what great selling looks like.

Matt Benelli sits down with sales veteran and Calm Ocean Sales founder Mike Muhlfelder for a no-BS conversation every CRO and sales leader needs to hear. With three decades of experience at companies like Oracle, IBM, and Jitterbit, Mike shares his unfiltered perspective on what’s gone wrong in modern B2B sales from bloated pipelines and broken qualification processes to tech stacks that mask, rather than solve, performance problems. If you’re relying on BANT and 4x pipeline math to hit your number, Mike says it’s time to wake up.

Listeners will learn why great reps don’t always make great leaders, how to use the “Four W’s” to qualify real opportunities, and why many teams are scaling mediocrity with automation. Mike also offers hard-won advice for CROs under boardroom pressure, and a stark reminder to protect your health and values as you chase performance. It’s part strategy, part therapy, and all signal, no noise.

Top Takeaways 
1. Great salespeople don’t always make great sales leaders.
Mike challenges the myth that success as a rep naturally translates to leadership, emphasizing that leading a team requires a completely different skillset.

2. Stop promoting outsiders into sales leadership roles.
Bringing in non-sales professionals to run sales teams often fails because they lack the experiential knowledge and empathy to lead sellers effectively.

3. Sales is a profession and must be treated like one.
Like finance or engineering, sales requires continuous training, discipline, and a commitment to mastery, not just charisma or improvisation.

4. Outdated qualification methods like BANT hurt your deals.
BANT is adversarial and obsolete; it leads to mistrust and surface-level qualification instead of real discovery.

5. Use the ‘Four W’s’ to qualify deals more accurately.
Mike’s framework: What happened? Why now? Who owns the project? When do they need to be live? Creates human-centered, business-grounded qualification.

6. The pipeline problem is systemic, not just executional.
Teams rely on inflated pipelines and 4–5x coverage ratios because poor qualification and forecasting have become normalized.

7. Most sales tech stacks enable mediocrity at scale.
Without sound fundamentals, even the best tools just help teams do the wrong things faster.

8. Sales math still matters: maximize yield, minimize waste.
Effective revenue leaders think like manufacturers, optimizing the fewest inputs (leads) for the highest output (closed deals).

9. Salespeople must take ownership of their own development.
With unlimited learning resources available, Mike urges reps to stop waiting for enablement and start taking personal accountability.

10. CROs must prioritize clarity, courage, and communication.
From cleansing the pipeline to resetting board expectations, Mike says leadership means telling hard truths and doing the right thing even when it’s unpopular.

11. Burnout is real, and it’s not worth it.
He ends with a human message: no job is worth sacrificing your health, family, or identity, no matter how big the number.

Sales enablement isn’t just a support function anymore; it’s a measurable, strategic driver of revenue growth. In this episode of Coach2Scale, Pam Dake, Senior Director of Go-To-Market Enablement at Menlo Security, shares how enablement must evolve from ad hoc product training into a disciplined, data-driven engine that shrinks sales cycles, improves pipeline velocity, and makes forecast calls more predictable. Pam challenges outdated views of enablement as an "art" form and shows why top organizations are treating it as a science rooted in customer outcomes, operational consistency, and frontline manager empowerment.

Listeners will walk away with clear strategies for transforming enablement into a competitive advantage: focusing on buyer needs instead of product specs, creating scalable and repeatable coaching frameworks, driving real behavior change at the rep level, and equipping frontline managers to move beyond firefighting into true people development. If you're a CRO or sales leader under pressure to deliver results faster and with fewer resources, this conversation is a must-listen.

Key Takeaway

• Sales Enablement Is a Science, Not an Art

Enablement must be tied to measurable business outcomes like deal velocity, quota attainment, and reduced stage duration times, not just soft skills or training events.

• Product Training Is Not Go-To-Market Enablement

True enablement focuses on customer challenges, value selling, and behavioral change, not just teaching reps how to pitch features.

• Frontline Managers Are Overwhelmed and Underequipped

Managers today are drowning in administrative tasks and deal management, leaving little time or structure for effective rep coaching and skill development.

• Consistency Beats Random Acts of Enablement

Scalable, repeatable programs with predictable operating cadences outperform sporadic, one-off training initiatives every time.

• Enablement Needs to Be a Strategic Business Partner

When properly positioned, enablement acts as the connective tissue across product, marketing, customer success, and sales, driving better internal alignment and faster revenue cycles.

• Coaching Is the Unlock for Talent Development and Retention

Teaching managers how to coach systematically, not just manage deals, creates higher performing teams and reduces regrettable attrition.

• Data Should Guide Enablement, Not Just Support It

Access to CRM, conversation intelligence, and engagement data enables the diagnosis of root causes of performance gaps and the prescription of targeted, timely interventions.

• The Inflection Point for Hiring Enablement Is Process Predictability

Companies should invest in enablement when there is some repeatability in the sales motion, ensuring that coaching scales what’s working rather than patching what’s broken.

• Enablement Can and Should Tip the Scales in Competitive Deals

Organizations that embed enablement into product launches, account strategies, and deal execution cycles are better equipped to win high-stakes opportunities.

Ways to Tune In:
Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
YouTube: https://www.youtube.com/@Coach2Scale 
CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

In this episode of Coach to Scale, sales trainer and former Olympic trials athlete Neil Wood joins Matt Bonelli to challenge one of the most pervasive mistakes CROs and sales leaders make: reserving coaching only for the bottom performers. Drawing from decades of real-world experience and high-performance athletics, Neil makes the case for why top sales reps need consistent, skill-based coaching just as much as, if not more than, struggling reps.

From tactical strategies to improve frontline manager execution to the psychological traps that stall rep development, Neil and Matt explore why most sales training fails to stick, what a real coaching culture looks like, and how reinforcement (not rah-rah) builds consistent revenue teams. If you’re serious about sales performance, this episode breaks down what separates good teams from elite ones and why your top talent should be the first to get coached.

Key Takeaways 

1. Training without reinforcement is a waste of money.
Neil argues that without structured follow-up, most sales training is forgotten within days and never translates to behavior change

2. Coaching should start with your top performers, not your bottom 20%.
Investing in your best reps delivers the highest ROI and accelerates performance gains that actually move the revenue needle.

3. Frontline managers aren’t equipped — or supported — to coach well.
Most FLMs were great reps, not trained coaches, and they’re overwhelmed with data, admin tasks, and deal reviews that crowd out skill development
.

4. The sales profession suffers from a lack of real coaching.
Neil defines true coaching as helping reps develop long-term skills, not just managing pipelines or offering encouragement.

5. Consistency matters more than intensity.
Regular coaching conversations — even 30 minutes every two weeks — drive more lasting impact than sporadic bursts of inspiration or annual sales kickoffs.

6. Behavior change happens through accountability and shared success.
Neil’s approach includes peer story sharing post-training to reinforce skills and inspire adoption through social proof, not just instruction.

7. You can't improve what you don't inspect.
Many managers accept rep narratives at face value; Neil stresses the importance of inspecting behaviors, not just outcomes, to drive improvement.

8. Coaching isn't a sign of weakness — it's what elite performers seek.
From Olympic athletes to UFC champions, Neil reminds us that the best in the world all have coaches — and they invest in sharpening their edge.

9. A good 1:1 isn't a therapy session or a deal inspection — it's a coaching moment.
Neil reframes 1:1s as intentional moments for skill growth, not check-the-box meetings or emotional downloads.

10. Similarities don’t sell — differences do.
Sales reps must stand out with a differentiated value proposition, and so must sales organizations when it comes to coaching their teams.

Ways to Tune In:
Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
YouTube: https://www.youtube.com/@Coach2Scale 
CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

In this episode of Coach to Scale, we sit down with Tony Burnside, SVP of APJ at Netskope, to dismantle the outdated playbook on sales leadership. Tony challenges the myth that effective managers need to lead through pressure, fear, or control. Instead, he shares his approach to building high-performing, culturally aligned teams, starting with hiring good humans, creating space for accountability, and making coaching a non-negotiable part of the manager’s role. With over 200 reps across 15 countries under his leadership, Tony’s insights are battle-tested and globally relevant.

We dig into what it takes to scale culture across borders, what most leaders miss in their 1:1s, and why every resignation is, as Tony puts it, “a performance review for leadership.” Whether you’re a CRO trying to stabilize performance or a frontline leader drowning in deals and check-the-box coaching, this episode delivers practical frameworks and hard-earned lessons for leveling up your org without burning out your team.

Key Takeaways:
1. Culture drives performance, not charisma or control
Burnside argues that strong sales cultures don’t emerge from aggressive personalities but from clarity, consistency, and mutual respect across the organization.

2. Good human first" is a hiring filter, not a luxury
He prioritizes character over credentials, explaining that people who want to win as a team outperform lone wolves in the long run.

3. Every resignation is a leadership review.
Attrition isn’t just HR’s concern; Tony reframes it as direct feedback on your leadership brand and your managers’ effectiveness.

4. Yes, you can be friends with your reps  if you’re still willing to hold them accountable
Burnside pushes back on the false tradeoff between camaraderie and performance, noting that trust and accountability aren’t mutually exclusive.

5. Global coaching cultures require local empathy.
Leading in APJ taught him that you can’t copy-paste U.S. management styles into Japan or India; success comes from adjusting expectations and coaching cadence to cultural norms.

6. Managers need a litmus test for connection and respect
He shares a personal test: if you wouldn't grab a drink with a rep while traveling, they may not be the right cultural fit for your team.

7. Most managers don’t know how to coach because they were never taught
Tony calls out the common pattern of promoting star reps without equipping them to lead, which leads to tactical, deal-centric 1:1s instead of skill development.

8. He invests personally in his own growth and expects others to do the same
From Dale Carnegie to Sandler, Tony’s career changed after he paid out of pocket for training; he sees self-investment as a signal of leadership potential.

10. Coaching must be operationalized, not left to chance or personality
Informal, unstructured coaching creates inconsistency and lost opportunities; managers need frameworks and tools to coach effectively at scale.

Ways to Tune In:
Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
YouTube: https://www.youtube.com/@Coach2Scale 
CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Tom Young, VP of Sales at BMC Software, joins Matt Benelli to challenge outdated assumptions about how enterprise sales should work. Drawing on decades of experience and a recent moment on the other side of a buying decision, Tom reveals how sellers often leave buyers to navigate complex purchasing decisions alone, leading to stalled deals, weak adoption, and low rep confidence. The problem isn’t buyer intent. It’s a lack of structure, coaching, and guidance.

This conversation gets tactical and strategic. Tom breaks down the myth that buyers know how to buy, why seller-led engagement models outperform passive following, and how high-performing FLMs simplify complexity through coaching, not control. CROs and sales leaders will appreciate the clear through line: when managers teach reps how to lead a buying journey, not just chase a number, sales cycles shorten, win rates improve, and performance becomes repeatable. If you’re building a scalable sales org, this is a must-listen.

Top Takeaways

• Enterprise buyers often don’t know how to buy software
  Despite assumptions, many buyers lack a defined decision process, which means sellers must guide, not follow, their journey.
• The best salespeople act as guides, not followers
  When sellers proactively lead buyers through a structured engagement model, the experience improves and adoption increases.
• Mutual Action Plans need to go beyond the PO date
  Ending your plan at "PO received" signals self-interest; the real impact comes from aligning with the customer’s go-live and success milestones.
• Effective FLMs sell the engagement model, not the product first
  Top-performing managers train reps to win by selling how the decision will be made, not just what to buy.
• Sellers must ask the questions buyers should be asking themselves
  High-quality discovery isn't just fact-finding; it helps buyers clarify their own thinking, build confidence, and reduce internal friction.
• Sales cycles fail when reps abdicate process control
  Letting the buyer “drive” often results in delays, missed stakeholders, and no decision; a structured engagement keeps momentum.
• Managers must balance pressure with coaching
  Pushing deals without guiding reps through skills and behavior leads to burnout and underperformance.
• You can’t outsource coaching and rep development
  Even strong enablement and RevOps support can’t replace the day-to-day behavioral coaching frontline managers must deliver.
• One-on-ones are not for pipeline inspection—they’re for skill development
  Coaching isn’t about the forecast; it’s about improving rep effectiveness so the forecast becomes more predictable.
• Every manager needs a consistent, inspectable operating rhythm
  Without structured 1:1s and repeatable frameworks, rep development becomes ad hoc, and performance becomes unpredictable.

Ways to Tune In:
Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
YouTube: https://www.youtube.com/@Coach2Scale 
CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

In this conversation of Coach the Scale, host Matt Benelli sits down with Michael Janes, CRO, investor, and co-founder of Rapid Commercialization Partners, to explore why top sales leaders are shifting their focus upstream. Janes unpacks his core philosophy: Sell to the strategy behind the capital, revealing how understanding a company’s ownership structure, whether private equity, venture-backed, or founder-led, can dramatically reshape how reps position value, influence internal champions, and align with executive priorities.

From myth-busting the idea that activity volume alone drives results to challenging how most one-on-ones miss the mark, Janes offers a grounded yet forward-looking perspective on what it takes to lead high-performance sales organizations. Listeners will walk away with practical insights on coaching beyond the forecast, the dangers of “super rep” management, and why the real leverage often starts at the board level, not the buying committee. If you’re a CRO or sales leader aiming to uplevel your team and shorten the path to influence, this conversation is required listening.

Key Takeaways:
1. Sell to the strategy behind the capital
Don’t just “follow the money”—understand the investor’s goals and align your sales motion to how capital is deployed, managed, and expected to grow.

2. Coaching needs to shift from deal review to skill development
Most one-on-ones are ineffective because they focus on forecasting instead of developing the behaviors that lead to consistent performance.

3. One-on-ones are broken when they lack preparation and structure
Great coaching starts with preparation; otherwise, reps get a therapy session or a pipeline interrogation, not actual development.

4. Sales managers are overwhelmed and under-equipped
FLMs are juggling too many priorities with little training on how to coach or drive rep performance—this gap undermines quota attainment.

5. Activity without purpose is a myth that needs killing
The old-school mindset of “just make more calls” misses the point; consistency only matters if it’s paired with relevance and precision.

6. Start high and cascade down—not the other way around
The most strategic salespeople begin with senior-level conversations, understanding investor priorities, then work downward to shape the internal sale.

7. Internal champions are built through strategic guidance, not feature pitching.
Could you make sure to provide your buyers with the narrative they need to sell internally by aligning your message with capital goals and business outcomes?

8. Overlay roles only work when they add real value
Janes proved that overlays focused on investor relations can be a force multiplier—but only if they help reps access decision-makers and frame deals through a capital lens.

9. Respect the chain of command—but don’t ask permission
When engaging PE or VC boards, it's critical to keep execs in the loop without letting them gatekeep the conversation.

10. Managers need enablement, too—not just reps
The assumption that great reps make great managers is flawed; without systems, training, and coaching support, FLMs can’t scale performance across the team.

Ways to Tune In:
Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
YouTube: https://www.youtube.com/@Coach2Scale 
CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

In this episode, bestselling author and CEO of Blind Spots, Kevin McCarthy, shares a deeply personal story of how unchecked blind spots, not bad intent, can quietly derail careers, culture, and company performance. After spending 33 months in federal prison for a white-collar crime he didn’t knowingly commit, Kevin emerged with a mission: help leaders see what they’re not seeing before it costs them everything.

When top performers become first-line managers, most are handed the title without the tools. We explore why so many sales managers default to deal reviews instead of skill development, how perception gaps fracture team trust, and why most coaching is misnamed and misdirected. Kevin breaks down the cognitive science behind decision-making under pressure and explains how poor coaching hygiene is driving regrettable attrition. This conversation hits directly at the heart of today’s frontline execution crisis and offers a clear path forward for CROs who want to scale with integrity.

Top Takeaways: 

• Blind spots—not bad intentions—derail leaders. Kevin’s story underscores that well-meaning leaders can still make costly mistakes if they lack self-awareness and critical thinking under pressure.
• Perception gaps destroy trust and performance. The difference between how a manager intends to communicate and how it's received can lead to misalignment, demotivation, and attrition.
• Sales managers are promoted, not prepared. High-performing reps are often elevated into management without training in people leadership, coaching skills, or emotional intelligence.
• Most sales coaching isn’t actually coaching. Managers default to forecasting and deal reviews, missing the opportunity to develop reps’ skills in a systematic and personalized way.
• One-size-fits-all management breaks teams. Kevin explains how failing to adapt your coaching style to each rep’s communication style and mindset leads to disengagement.
• The hardest job in the company is being ignored. First-line managers juggle execution, admin, and development but rarely get the support, tools, or training to coach effectively.
• Reps leave when they don’t feel developed. Talent walks when managers only talk numbers. Real coaching connects with reps’ goals, strengths, and growth trajectory.
• Self-awareness is the most underdeveloped leadership skill. Kevin makes the case that improving self-awareness and emotional intelligence in managers is the single best lever for improving sales culture.
• Frontline execution problems are strategic risks. What looks like a rep issue is often a management system failure—CROs must prioritize manager enablement if they want predictable performance.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Matt Benelli sits down with Mike Montague, sales and marketing expert at Avenue9 and host of the Human-First AI Marketing podcast, for a candid conversation about what sales managers are still getting wrong about coaching. From the myth that leaders need to have all the answers to the burnout caused by "super reps" turned managers, Mike breaks down why most 1:1s fail and how asking better questions can flip the script on team performance. If you're still equating pipeline reviews with coaching, this one’s for you.

They also unpack the critical gap between coaching and execution and why online learning and conversation intelligence tools fall short without behavior change. Mike shares his "Iron Man vs. Terminator" analogy to help sales leaders reframe their use of AI and makes the case for exposure therapy and tough love as the missing ingredients in most sales organizations. Whether you’re trying to scale performance or stop regrettable attrition, this episode gives frontline and senior leaders a roadmap for more effective, accountable teams.

Top Takeaways:

• Coaching is about asking questions, not giving answers. Managers who try to “know it all” become bottlenecks; real coaching empowers reps to think for themselves.
• The best leaders make themselves irrelevant. Like elite sports coaches, great sales leaders build systems and skills so teams can operate independently.
• AI won’t replace salespeople, but it will replace those who don’t use it. Sales leaders need to think like Ironman, using AI as an enhancement tool to increase awareness and execution, not as a replacement for human strategy.
• The frontline sales manager (FLM) role is the hardest in the company. FLMs are overwhelmed by tasks, undertrained in coaching, and lack the time or tools to develop their teams effectively.
• Selling someone what they need and can afford isn’t cheating—it’s your job. Sales should focus on qualified buyers with budget, authority, and urgency, not on convincing disinterested prospects.
• Coaching fails when it focuses only on deals, not skills. Most coaching sessions are just pipeline reviews; they don’t address the behaviors that improve performance in the long term.
• Exposure therapy is essential for growth. Managers need more reps, not more theory, to improve at hard conversations or high-stakes moments.
• Online learning is helpful but only if it’s paired with feedback and behavior change. Asynchronous learning tools often reinforce what reps already know; without coaching moments, they don’t close performance gaps.
• Managers who need approval frequently avoid necessary conversations. Leadership requires discomfort, and effective managers must overcome the urge to be liked to hold reps accountable.
• Coaching is different from managing—and most people don’t know how to do it. There's a widespread misunderstanding of coaching; most FLMs were never taught how to develop others, and it shows.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Every sales leader has heard the mantra: “Pipeline cures all.” But what if that’s only half the truth? In this episode, Matt Carey, SVP of Global Sales at FIS, breaks down why more pipeline isn’t always the answer—the right pipeline is. He shares hard-earned lessons from leading sales teams at Oracle, SAP, and FIS, explaining how top-performing organizations prioritize quality over quantity, measure pipeline health beyond raw coverage, and avoid common forecasting pitfalls.

Matt also explores the real role of frontline managers, not as super reps, but as force multipliers who elevate their teams. He discusses hiring strategies that separate true performers from resume fluff, the importance of post-mortem loss reviews, and why most companies still get coaching wrong. Whether you're a CRO, VP of Sales, or a frontline manager looking to level up, this conversation is packed with insights that will change the way you build and manage your pipeline.

Top Takeaways:

• Pipeline Quantity vs. Quality – More pipeline doesn’t guarantee success; leaders must focus on the right pipeline by assessing deal quality, aging, and true viability.
• The Problem with "Just Add More Pipeline" Thinking – Sales teams often flood CRMs with unqualified deals to meet coverage targets, leading to bloated and misleading forecasts.
• Why Frontline Managers Must Stop Being Super Reps – The best managers don’t just close deals for their teams; they enable reps to develop the skills to win consistently.
• Hiring Based on Past Performance, Not Promises – Great sales hires have a history of winning, regardless of industry or background; track record matters more than potential.
• Loss Reviews Are More Valuable Than Win Reviews – Studying why deals were lost provides deeper insights into messaging gaps, pricing misalignment, and product fit issues.
• How Sales Leaders Sell Internally – At higher levels, sales leaders spend as much time selling internally for budget, resources, and strategy alignment as they do selling to customers.
• Coaching Needs a System, Not Just Good Intentions – Too many one-on-ones are either deal reviews or therapy sessions; real coaching needs structure, accountability, and a focus on skill development.
• Managing a Global Sales Team Requires Cultural Awareness – Sales leaders must adapt their messaging and approach across markets, respecting regional differences in business etiquette and buying behavior.
• The Shift from Tactical to Strategic Leadership – Senior sales leaders must move beyond the day-to-day deal cycle and focus on long-term market positioning, competitive threats, and team scalability.
• Why Sales Leaders Must Track Trends, Not Just Deals – The best leaders analyze broader win-loss data, competitive shifts, and industry changes to refine strategy, not just react to individual deal outcomes.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Performance improvement plans (PIPs) are meant to help struggling reps, but more often than not, they’re just a step toward the exit. So why do they fail? And what should CROs and frontline sales managers do instead to truly develop their teams? Why does urgency hurt your coaching?

In this episode of Coach2Scale, host Matt Benelli sits down with Eric Hachmer and Steve Frappier of High Five Advisory to uncover the biggest mistakes sales leaders make when it comes to coaching and accountability. They break down why rigid sales policies backfire, how “one-size-fits-all” coaching kills performance, and the key to turning struggling reps into consistent performers. Whether you’re leading a team or coaching the coaches, this episode is packed with real-world insights on what actually drives long-term sales success.

Top Takeaways:

• Performance Improvement Plans (PIPs Often Fail) – PIPs are typically used as a last resort before termination rather than as a true coaching tool; leaders should focus on proactive development instead of reactive intervention.
• One-Size-Fits-All Coaching Doesn't Work – Every rep has different learning styles, motivations, and challenges, so great leaders tailor their coaching approach to individual needs instead of using a rigid playbook.
• Sales Policies Can Hurt More Than Help – Relying too much on black-and-white sales policies can create roadblocks for both customers and reps, whereas flexibility and good judgment lead to better outcomes.
• Good Leaders Focus on Behaviors, Not Just Results – The best sales managers don’t just chase numbers; they work to change the behaviors that drive performance, ensuring long-term success.
• Listening Is a Leader’s Superpower - Effective coaching starts with understanding. Great leaders take the time to listen before jumping to solutions, which builds trust and improves team engagement.
• Accountability Goes Both Ways – Reps should be held accountable for performance, but managers also need to take ownership of removing roadblocks, providing support, and developing their people.
• Urgency Can Get in the Way of Coaching – Sales leaders often move fast and focus on immediate results, but taking the time to coach properly leads to sustainable, long-term performance improvements.
• Trust and Authenticity Are Non-Negotiable – The best sales leaders show up as their true selves, follow through on their commitments, and create environments where reps feel supported, not micromanaged.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Too many sales teams operate on instinct, hoping charisma and hustle will carry them to quota. However, Paul Fannon, Global CRO at Bottom Line, views sales as a science. In this Coach to Scale episode, Paul explains why a structured, data-driven approach is the key to predictable success. He shares how top reps aren’t necessarily the most talented—they’re the most disciplined. You’ll hear why work ethic can’t be taught but can be uncovered, how sales leaders should adapt their coaching style to each individual, and why frontline managers need continuous development to succeed.

We also explore Paul’s philosophy on “no wasted sales calls” and how technology should serve sales teams, not distract them. Learn why getting a clear yes or no is better than living in the limbo of “maybe,” how to avoid the biggest coaching mistakes, and what separates high-performing sales organizations from those that struggle. If you’re a CRO or sales leader looking for practical insights on driving efficiency and effectiveness, this conversation is a must-listen.

Top Takeaways:

• Sales is a Science, Not an Art – Success in sales isn’t about charisma; it’s about following a structured process, leveraging data, and executing consistently.
• No Wasted Sales Calls – Every call should be targeted and strategic, ensuring reps engage with the right prospects at the right time to drive meaningful outcomes.
• Work Ethic Can’t Be Taught, But It Can Be Uncovered – Some reps have the drive but don’t realize it; great leaders help bring it out through the right environment and expectations.
• Frontline Managers Are the Key to Sales Success – Strong sales organizations don’t just develop reps; they invest in managers who can coach, hold teams accountable, and drive performance.
• One Process, Many Coaching Styles – While sales organizations need a standardized process, managers must adapt their coaching approach to each individual’s motivations and learning style.
• Consistency Beats Talent – The most successful sellers aren’t always the most naturally gifted; they’re the ones who show up every day, follow the process, and put in the work.
• Data-Driven Selling Reduces Risk – Reps and managers who rely on gut instinct often struggle with inconsistency; using data ensures repeatable success and predictable pipeline growth.
• Decisiveness Matters More Than "Maybe" – The worst outcome isn’t hearing “no,” it’s being stuck in limbo; great salespeople know how to get clear answers and move deals forward.
• Technology Should Serve Sales, Not Distract From It – Sales tech should help reps focus on high-quality calls and pipeline movement, not overwhelm them with unnecessary complexity.
• Coaching Should Go Beyond Deals – Many managers only focus on pipeline and forecasting, but real sales growth comes from coaching skills, behaviors, and long-term development.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Sales leadership is full of hidden pitfalls that can derail even the most experienced managers. In this episode, Kevin Gaither—former ZipRecruiter sales leader, CRO of Inside Sales Expert, and author of It Happened on the Sales Floor—pulls back the curtain on the most common mistakes sales managers make. He challenges the myth that you can be friends with your reps, shares the six must-have traits for every sales hire, and explains why most coaching efforts fall flat. If you’re a CRO or frontline sales leader, this conversation will change how you think about hiring, coaching, and managing your team.

Kevin’s straight-shooting approach delivers hard-earned lessons from building and scaling high-growth sales teams. We cover why many first-time managers fail, how to identify coachable reps, and the key to developing a sales culture that breeds success. Whether you’re struggling with underperforming reps, overwhelmed managers, or a lack of accountability, this episode offers actionable strategies to avoid costly leadership missteps and build a team that consistently wins.

Top Takeaways:

• You Can’t Be Friends with Your Sales Reps – Building personal friendships with your team creates favoritism risks, weakens accountability, and can backfire when tough decisions need to be made.
• Hire for Six Non-Negotiable Traits – Every great sales hire must have need for achievement, competitiveness, optimism, coachability, continual learning, and organizational skills—if they’re missing even one, don’t hire them.
• Coaching Is More Than Just Deal Reviews – Most managers only coach around pipeline and forecasting, but real coaching focuses on skill development and long-term rep growth.
• First-Time Managers Fail Without Proper Training – Many sales leaders assume they can manage just because they were top reps, but without structured training, they struggle to develop their teams effectively.
• A Strong Hiring Process Is the #1 Predictor of Sales Success – The best sales strategy in the world won’t work if you put the wrong people in the seats—hiring is the most critical leadership skill.
• Reps Don’t Change Just Because You Want Them To – Without consistent coaching, accountability, and reinforcement, reps will default to old habits, no matter how much you tell them to improve.
• Perception Is Reality in Sales Leadership – Even if you treat your team fairly, if others perceive favoritism or inconsistency, it will erode trust and team cohesion.
• Managers Need a Playbook, Not Just Experience – Experienced managers still need structure and frameworks to be effective; winging it leads to inconsistent coaching and missed opportunities for rep development.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Most sales leaders focus on hitting their numbers, but few take the time to diagnose why their teams struggle in the first place. In this episode, Bob Tharp, a seasoned sales leader with 35+ years in complex solution sales, reveals the hidden obstacles that stall revenue growth and how CROs can fix them. From controlling the controllables to holding reps accountable without micromanaging, Bob shares a practical, no-nonsense approach to building a high-performing sales organization.

Join host Matt Benelli as he and Bob dive into the biggest coaching mistakes sales leaders make, why most 1:1s fail to drive real improvement, and how AI-driven coaching can transform frontline managers into true performance multipliers. If you’re tired of surface-level sales advice and want real strategies to improve your team’s execution, this episode is a must-listen.

Top Takeaways:

• Sales success starts with diagnosing the real issues, not just chasing numbers. Many organizations focus on revenue targets without addressing the root causes of underperformance, leading to recurring problems.
• Sales coaching must be holistic, considering both macro and micro factors. Effective coaching looks beyond individual rep performance to evaluate how company strategy, sales processes, and cross-functional alignment impact results.
• Control the controllables—great salespeople take ownership of their success. Reps can’t always change their environment, but they can control their mindset, activity level, and how they adapt to challenges.
• Most managers struggle with accountability because they avoid tough conversations. Leaders often delay difficult discussions, leading to prolonged underperformance and a culture of low expectations.
• One-on-ones should focus on skill development, not just deal reviews. Many sales managers default to discussing pipeline, but the most impactful 1:1s prioritize coaching reps on behaviors that drive long-term success.
• Emotional intelligence is critical for coaching and leadership. Effective leaders read the room, de-escalate tense conversations, and guide reps to self-discovery rather than dictating solutions.
• AI-powered sales tools are valuable, but human coaching is irreplaceable. Platforms like Gong and SixSense provide insights, but without human judgment and structured coaching, they’re just another dataset.
• Top performers create their own opportunities instead of relying on inbound demand. Great sales reps don’t just wait for leads; they proactively diagnose customer pain points and create demand through consultative selling.
• Sales leaders must stop thinking like super reps and start thinking like business owners. Instead of jumping in to save deals, effective managers build systems that develop reps and create scalable, repeatable success.
• Consistency in coaching is the key to sustainable growth. Sporadic coaching sessions don’t drive behavior change—regular, structured coaching ensures reps continuously improve and hit their targets.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Thad Zilka, a veteran leader in sales and leadership, discusses the transformative power of coaching in sales performance. Drawing insightful parallels to the world of sports, Thad challenges the notion that star salespeople don't need guidance. Through sharing his own journey, he highlights the pivotal role of structured business plans and the consistent need for accountability to truly achieve greatness. His perspective provides a refreshing look at how even seasoned professionals can benefit from external coaching to elevate their skills from good to exceptional.

We explore the intriguing role of AI in the field, balancing its impressive capabilities with the irreplaceable human touch. AI tools are revolutionizing data analysis and idea generation, yet Thad and Matt caution against losing the personal connections that are foundational to successful sales interactions. The conversation expands to the career trajectories of sales professionals and the often-misguided rush towards management roles, urging a mindful approach to career decisions and recognizing the true decision-makers in complex sales environments.

Passion and persistence become the heart of our narrative as we dive into the vibrant world of gold investment and the lifelong dedication of being a Kiss fan. We share a mix of encounters and personal stories, from rock concerts to collecting memorabilia, all underscoring the power of perseverance in both life and business. The episode wraps up with reflections on influential leaders like Zig Ziglar and Ronald Reagan, emphasizing the essence of emotional intelligence and the noble art of sales. Join us for a considerable list of insights that promise to inspire, educate, and entertain.

Top Takeaways:

• Even the best sales reps need coaching. Hiring great talent isn’t enough—without continuous coaching, even experienced reps can reinforce bad habits.
• A strong business plan keeps reps accountable. Sales professionals should have a personal business plan with clear 30-, 60-, and 90-day goals that managers actively track.
• Tough conversations are necessary for growth. Great leaders don’t avoid difficult discussions; they address performance issues head-on by asking direct questions and reading between the lines.
• Self-awareness and emotional intelligence (EQ) are essential. The best managers don’t just listen—they watch for body language, energy shifts, and unspoken struggles to understand what’s really going on.
• AI should enhance coaching, not replace it. AI can surface coaching insights, identify patterns, and save time, but human connection and emotional intelligence are irreplaceable.
• One-on-ones should focus on development, not just deals. Many managers fall into the trap of turning 1:1s into pipeline reviews instead of using them to build rep skills and long-term success.
• Not every great salesperson should become a manager. Many top reps feel pressured to move into leadership, but management requires a different skill set that isn’t right for everyone.
• Sales leadership is about removing obstacles. The best managers clear roadblocks, eliminate bureaucracy and create an environment where their team can focus on selling.
• Coaching consistency separates good teams from great ones. Sporadic feedback doesn’t drive lasting change—regular, structured coaching ensures continuous improvement and accountability.
• The role of sales managers is harder than ever. With more responsibilities and less time, FLMs need better tools and processes to coach effectively without getting overwhelmed.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

What if the secret to transforming your sales team lies within the art of the one-on-one meeting? Join me, Matt Benelli, and our special guest, Andy White, VP of Sales at Trivy, as we debunk myths and uncover these meetings' critical role in building trust and alignment in modern sales teams. We dive into the heart of creating coaching cultures and learn why remote and hybrid work environments make these interactions more indispensable than ever. Andy shares his expertise aligning team and company goals while fostering accountability and connection through structured, meaningful conversations.

This enlightening discussion reveals a powerful framework for one-on-one meetings that can propel your team's performance to new heights. With categories focusing on personal, professional, and future-facing topics, we explore how leaders can effectively navigate hiring challenges and compensation expectations. Andy sheds light on crafting an operating guide for leaders that enhances communication and accountability, making even the most challenging conversations manageable while nurturing a supportive and growth-focused environment.

Prepare to rethink leadership strategies as we examine the transition from frontline management to executive roles, highlighting the importance of consistency, problem-solving, and AI tools that revolutionize sales efficiency. You'll hear about innovative solutions like Zinnia and cost-effective platforms that boost productivity and improve customer experiences. As we close, discover how Trivie's approach to corporate training through gamification and personalization can bridge knowledge gaps, ultimately driving sales success. Whether you're looking to refine your leadership skills or explore the intersection of AI and sales, this episode promises a wealth of valuable insights.

Chapters:
(00:00) - Building Sales Leadership Trust and Alignment

(10:14) - Effective Framework for Productive One-on-Ones

(15:30) - Building Trust Through Effective One-on-Ones

(20:33) - Effective Communication in Leadership Accountability

(31:51) - Leveraging Consistency and Problem-Solving Skills

(38:12) - Leveraging AI Tools for Sales Efficiency

(44:33) - Coaching Impact and Fundamentals

Key Takeaways:

• The One-on-One Meeting is Not Dead, But It is Often Ineffective - Many sales leaders neglect or mismanage one-on-ones, reducing them to deal reviews instead of meaningful coaching conversations.
• Trust is the Foundation of Effective Coaching - Sales representatives need to feel supported and valued before they will fully engage in coaching and performance discussions.
• A Structured One-on-One Framework Drives Better Outcomes - Breaking meetings into personal check-ins, professional development, and future planning ensures that they remain productive and aligned with long-term growth.
• Managers Must Focus on Skill Development, Not Just Deal Status - Coaching should prioritize behaviors and competencies that lead to better sales results rather than simply tracking pipeline updates.
• Asking Sales Reps for Feedback Strengthens Leadership - Inviting feedback on management effectiveness fosters a culture of accountability and continuous improvement.
• Accountability is Essential for Driving Consistent Performance - Managers should document key action items from each meeting and follow up to ensure that coaching translates into tangible progress.
• Alignment is Crucial for Sales Success - When company goals, compensation structures, and sales objectives are misaligned, quota attainment suffers, and disengagement increases.
• Sales Leaders Must Be Problem-Solvers, Not Just Problem Identifiers - Senior leadership values managers who present solutions alongside challenges rather than simply escalating issues.
• AI Can Enhance Coaching and Improve Sales Effectiveness - Tools like CoachEm provide managers with data-driven insights, helping them conduct more impactful coaching sessions without adding to their workload.
• Companies That Prioritize Coaching Build More Resilient Sales Teams - Investing in structured coaching processes leads to higher quota attainment, lower turnover, and a stronger sales culture.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Can senior executives really afford to skip coaching? Join us for a fascinating discussion with Josh Horstmann, Operating Partner at Francisco Partners Consulting, as we dismantle the myth that top leaders don't need coaching. We promise you'll learn how to harness coaching for all levels of performance, from struggling team members to high-flying stars like UFC champion Jon Jones. Josh shares unique insights on smarter hiring, building a "virtual bench," and creating a coaching-centric culture that enhances both individual and organizational growth.

Experience the art of team building and leadership through a sports lens as we explore the parallels between business teams and elite sports teams. Josh reveals how understanding diverse personalities and strengths can lead to success, much like the winning strategies of top coaches like Andy Reid. Discover how hiring individuals who surpass your own skills in specific areas can elevate your team’s performance and why being present in coaching conversations is paramount. We’ll guide you through creating a balance between strategy and execution, ensuring leaders are equipped to navigate career transitions and avoid the pitfalls of hasty promotions.

Unlock the secrets to effective leadership attributes that drive success, especially during company acquisitions. Josh delves into the qualities that distinguish thriving senior sales leaders, sharing his personal experiences with impactful coaching. Learn how self-awareness and a compelling narrative can transform your approach to leadership. As we conclude, we’ll touch on finding inspiration beyond the boardroom and the importance of seeing through an individual's lens to foster self-growth. This episode is filled with actionable insights and reflections to empower anyone in a leadership role.

Chapters:
(00:00) Myth of Not Needing Coaching
(04:28) Value of Coaching for High Performers
(11:16) Effective Team Building and Coaching
(16:10) Coaching Strategies for Leadership Success
(25:32) Navigating Career Transitions and Performance
(34:03) Effective Leadership Attributes for Success
(38:54) Empowering Potential Through Individual Lens

Key Takeaways:

• Coaching Isn’t Just for Underperformers – Even A players and executives need coaching to continue growing and refining their skills.
• Forecast Reviews Are Not Coaching – Too many one-on-ones focus solely on pipeline updates rather than skill development and long-term growth.
• The Best Performers Still Need Guidance – High performers benefit from strategic coaching on leadership, negotiation, and career development—not just deal execution.
• Top Reps Don’t Always Make the Best Managers – Selling and coaching are two different skill sets; promoting star reps without leadership training often leads to ineffective managers.
• Identify “Runners” vs. “Builders” in Leadership Roles – Some leaders excel at optimizing existing processes (runners), while others thrive in building something new (builders); knowing the difference is key to scaling effectively.
• Be Present and Intentional in Coaching Conversations – Effective coaching requires full attention, structured agendas, and follow-through—not distracted, last-minute check-ins.
• Ad Hoc Coaching Is Not a Substitute for Structured Development – Informal, on-the-fly coaching moments are valuable but should complement, not replace, scheduled coaching sessions.
• Building a “Virtual Bench” is Critical for Leadership Succession – Sales leaders should proactively develop and identify future managers before leadership roles open up.
• A Strong Coaching Culture Starts at the Top – If executives don’t prioritize coaching, it won’t become a sustainable practice throughout the organization.
• Organizations That Invest in Coaching Outperform Their Peers – Companies with a structured coaching culture see lower attrition, higher quota attainment, and stronger leadership pipelines.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Unlock the secrets to skyrocketing your sales growth with insights from Brent Holloway, the CRO and co-founder of SaaS Sales Advisors. Imagine doubling your company's revenue without expanding your sales force—Brent breaks down how understanding unit economics and refining customer profiles are key to achieving this. We navigate through the intricate layers of sales productivity and efficiency, uncovering how tailored strategies can lead to consistent, sustainable success.

Brent introduces us to the powerful sales velocity formula, a game-changer in understanding unit economics within sales teams. By dissecting essential metrics like win rates, average deal size, and sales cycle length, we explore how even a hypothetical mid-market team can transform its approach to sales, driving productivity and boosting profitability. Brent's approach challenges conventional tactics by emphasizing the importance of pursuing opportunities with high win rates and the critical need to refine strategies based on insightful patterns.

The conversation takes a futuristic turn as we consider the evolving landscape of sales practices since 2008, highlighting the enduring impact of "Sales 2.0" despite technological advancements. Brent shares personal anecdotes on scaling businesses, emphasizing a strategic balance between ambitious growth and judicious investments. We end on a high note by celebrating the role of mentorship and structured frameworks like GROW in overcoming adversity, both personally and professionally. This episode is a treasure trove of wisdom for sales leaders eager to optimize their strategies for enduring success.

Chapters:
(00:00) Sales Leadership and Unit Economics
(13:02) Improving Sales Productivity and Efficiency
(20:48) Sales Technology and Effectiveness Strategies
(31:42) Overcoming Adversity in Sales

Key Takeaways:

• Master Unit Economics: Understand and optimize the four sales velocity levers—opportunity volume, win rate, average sales price (ASP), and sales cycle length—to drive smarter, more efficient growth.
• Focus on ICP (Ideal Customer Profile): Tailoring your strategy to target the right customer segments improves efficiency, reduces wasted effort, and delivers higher-value deals in shorter timeframes.
• Coaching as a Multiplier: Structured, development-focused coaching—not just pipeline reviews—helps sales managers build consistency, accountability, and sharper rep performance.
• Leverage Data and AI: Using AI tools and analyzing historical data empowers leaders to identify winning patterns, optimize resources, and refine strategies for sustainable success.
• Scale with Balance: Avoid the pitfalls of overambitious growth by aligning headcount expansion with adequate investments in enablement, coaching, and supporting resources.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Unlock the secrets of genuine connection in sales and leadership with our guest Lane Monson, an executive leader and coach who challenges the conventional wisdom of salesmanship. Do most salespeople really know how to connect deeply with others? Discover what Lane has to say as we unravel the five levels of connection, which many sales professionals only partially navigate. Through Lane's insightful anecdotes, including a transformative experience with a Navy chaplain, learn how asking the right questions can turn ordinary interactions into significant, life-changing connections.

Explore the seven keys to achieving 1% success as a sales leader, starting with the realization that great leaders are essentially great coaches. This episode promises to reshape your understanding of leadership from traditional motivators to empathetic guides. Using an analogy from organic chemistry, Lane illustrates the journey through challenging phases, emphasizing belief, desire, and the power of perseverance. By focusing on individualized coaching and understanding unique team motivations, listeners will gain insights into building belief through small wins, fostering a vision-driven approach to leadership that prioritizes personal growth alongside team success.

Exceptional sales leaders are more than just business savvy—they're compassionate coaches who build meaningful connections. Through captivating discussions about figures like Michelle Potter and Joey Green, we emphasize the evolution from motivational tactics to genuine empathy in sales leadership. Lane's journey from CEO to executive performance coach offers lessons in lifelong learning, mentorship, and curiosity, encouraging listeners to embrace unexpected career shifts. Tune in to uncover valuable insights into becoming not just a successful leader, but also a compassionate facilitator of growth and connection within your team.

Chapters:
(00:00) Myth Busting and Connection in Coaching
(09:18) Leadership Strategies and Personal Development
(26:51) Leadership and Connection
(36:03) Lessons Learned and Executive Performance Coaching
(51:48) Coaching Insights and Connection Building

Takeaways:

1. Salespeople Overestimate Connection: Many salespeople believe they connect well, but they fail to ask high-value questions, listen deeply, or build trust effectively.
2. The 7 Keys to 1% Success for Sales Leaders: Success comes from great coaching, fostering belief and desire, defining vision and purpose, building deep connections, asking high-value questions, and maintaining a growth-focused mindset.
3. Purpose Drives Perseverance: Understanding individual and organizational purpose helps leaders and teams navigate challenges and stay committed.
4. Accountability Requires Carefrontation: Balancing candor and care (“carefrontation”) helps leaders hold teams accountable while maintaining trust and respect.
5. Personalized Coaching is Essential: Tailoring coaching approaches to individual team members’ motivations, goals, and personalities fosters better alignment and outcomes.
6. A Growth-Focused Mindset is Key: Leaders must challenge old thought patterns and adopt accurate, supportive beliefs to inspire their teams.
7. True Connection Comes from Understanding: Leaders who deeply listen, empathize, and value their team members create stronger trust and engagement.
8. Encouragement and Structure Build Morale: Over-delivering encouragement and using structured coaching frameworks improve morale and ensure consistent performance.
9. Overcoming Resistance Requires Empathy: Resistance in teams often stems from fear, fatigue, or lack of clarity, and leaders must address these with active listening and care.
10. Leadership Transports People: Great leaders act like coaches, helping individuals move from where they are to where they need to be by providing guidance and direction.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

What if sales success wasn’t just about the money? Join us as we challenge this age-old myth with insights from Jim Gannon, SVP of Sales at Sysdig. Discover how autonomy, competition, and a genuine drive to impact the business play pivotal roles in achieving sales excellence. Jim reveals why curiosity and the willingness to learn from peers set top performers apart, shedding light on the motivations that propel seasoned pros and ambitious newcomers alike.

The episode further unpacks the essence of team dynamics with a spotlight on recognition and accountability. By celebrating the collective efforts of everyone from sales engineers to onboarding teams, we uncover how fostering an inclusive culture strengthens team cohesion. Jim dives into the balancing act leaders face in maintaining a positive yet accountable environment, emphasizing the critical role of enablement and data-driven insights in recognizing high-performing teams.

Leadership and mindset take center stage as Jim shares his experiences leading in Japan, offering valuable lessons on cultural awareness and scalable processes. Explore how a winning attitude, even against fierce competition, can be nurtured within sales teams. From strategies for private companies to tales of overcoming odds in the sports world, this conversation is your playbook for elevating sales performance and leadership prowess. Don't miss Jim's engaging stories and practical advice that promise to inspire and transform.

Chapters:
(00:00) Busting Sales Myths With Jim Gannon
(12:08) Fostering Team Recognition and Accountability
(19:05) Enhancing Sales Enablement Through Accountability
(28:01) Building a Winning Mindset in Sales
(33:51) Enhancing Customer Success in Sales
(38:55) Casting a Leadership Shadow
(42:53) Cultural Awareness and Training Stories

Takeaways:

1. Sales Motivation Beyond Money: Jim Gannon challenges the common myth that salespeople are primarily driven by monetary incentives. He emphasizes that autonomy, competition, and the desire to impact the business are key motivators. Understanding these can help CROs better tailor their leadership and incentive structures.
2. Curiosity as a Differentiator: Top-performing salespeople often exhibit a strong sense of curiosity and a willingness to learn. CROs should foster an environment that encourages intellectual engagement and peer learning to enhance team performance.
3. Recognition and Accountability: Building a cohesive sales team involves recognizing contributions from all team members, not just those who close deals. CROs should focus on fostering a culture of inclusivity and accountability, which aligns with company values and encourages collective success.
4. Sales Enablement and Data-Driven Coaching: Effective sales enablement requires moving beyond content overload to live training sessions and leveraging tools like Gong for data-driven coaching. CROs should ensure their teams have access to insights that can improve performance and identify areas for development.
5. Building a Winning Mindset: In challenging market conditions, CROs should inspire their teams by sharing stories of underdogs who have succeeded against the odds. This helps instill confidence and drive, encouraging teams to execute the basics with excellence.
6. Cultural Awareness in Global Leadership: For CROs overseeing international teams, understanding cultural nuances is crucial. Jim's experiences in Japan highlight the importance of cultural sensitivity and the concept of a "leadership shadow" in global contexts.
7. Leveraging Competitive Spirit: Salespeople who thrive often enjoy the challenge of competing against larger, better-branded competitors. CROs can harness this competitive spirit by encouraging strategies that focus on differentiation and value delivery.
8. Balancing Inspirational Leadership with Accountability: Jim emphasizes the need for CROs to balance inspirational leadership with creating a culture of accountability. This involves setting high standards while motivating teams to achieve them through clear, consistent expectations and support.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

What if the secret to exceptional coaching lies not in having all the answers, but in embracing authenticity and vulnerability? Join us as we chat with Chris Michelmore, the head of mid-market acquisition at Zoom, who brings his unique perspective on coaching both athletes and salespeople. Chris challenges the notion that great coaches must be the best performers, instead highlighting the power of meeting individuals where they are and guiding them toward their goals. Through compelling anecdotes, Chris underscores the significance of building trust and genuine connections, paving the way for both personal and team success.

Our conversation hits effective coaching techniques, contrasting the "peanut butter coaching" approach with more personalized methods. Chris advocates for tailored strategies that align with individual and collective aspirations, emphasizing that true improvement requires more than a one-size-fits-all mindset. By understanding the diverse needs of team members, coaches can foster an environment where each person thrives, creating a balanced dynamic that enhances performance across the board. The discussion also touches on the delicate balance of emotional investment, highlighting the pitfalls of overcoaching and the importance of wisely allocating resources.

Chris's insights extend to the importance of feedback and communication, sharing lessons learned from both positive and negative coaching experiences. Through personal stories, he illustrates how bad coaching can be as instructive as good coaching, contributing to a coach's growth and adaptability. With nods to renowned coaches like Michael Phelps' coach, Bob Bowman, and Bill Walsh, Chris emphasizes the value of focusing on process and community over outcomes. This episode promises to enrich your understanding of coaching, leaving you with actionable insights to apply within your own teams.

Chapters:
(00:00) Coaching Salespeople With Authenticity
(09:32) Effective Coaching Techniques and Strategies
(22:23) The Pitfalls of Overcoaching
(26:34) Building Trust and Effective Communication
(34:09) Unveiling Coaching Potential and Pitfalls

Takeaways:

1. Embrace Authenticity and Vulnerability: Chris emphasizes the importance of authenticity in coaching. CROs should not feel pressured to have all the answers or be the best in the room. Instead, being genuine and vulnerable can foster stronger relationships and build trust within the team.
2. Personalized Coaching Over One-Size-Fits-All: Tailoring coaching strategies to meet individual team members where they are is crucial. Personalized coaching that aligns with individual aspirations helps bridge the gap between where they are and where they want to be, driving better buy-in and improvement.
3. Balance Team and Personal Goals: Effective coaching involves balancing team-wide objectives with individual goals. This ensures that both the collective and personal aspirations are met, enhancing overall performance and team cohesion.
4. Allocate Emotional Capital Wisely: Emotional resources are finite, and CROs must allocate them wisely. Overinvesting in individuals who do not reciprocate the effort can lead to burnout. Focus on empowering those who show genuine drive and willingness to succeed.
5. Learn from All Coaching Experiences: Both positive and negative coaching experiences offer valuable lessons. Even controversial coaches can provide insights into different methodologies that may be effective. CROs should maintain a growth mindset and continuously learn from various coaching styles.
6. Focus on Process Over Outcomes: Inspired by renowned coaches like Bob Bowman and Bill Walsh, Chris advocates for focusing on the process and community rather than solely on outcomes. By improving processes, the desired results will naturally follow.
7. Encourage Feedback and Build Trust: Creating an environment where team members feel comfortable providing feedback is vital. Acting on this feedback helps build reliability and trust, essential components for a successful coaching culture.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

As we close the book on 2024, I want to take a moment to say THANK YOU. Whether you tuned in for one episode or all 52, you're part of a movement that believes coaching is the rocket fuel for performance. This year, Coach the Scale recorded over 65 episodes, reaching thousands of sales leaders. But this isn’t about vanity metrics—this is about impact. Each episode brought lessons that slapped us in the face and whispered, "Pay attention."

So, let's hit rewind on the top 10 lessons from 2024 that every sales leader needs tattooed (metaphorically) on their brain:

1. Coaching isn’t teaching—it’s training for battle.
Your reps don’t learn to box by watching YouTube. It’s role plays, feedback, and reps that build champions.

2. High performers are your blue-chip stocks.
Feed them or someone else will. Stop spending all your energy on the bottom 20%.

3. Focus on behaviors, not just outcomes.
Outcomes lag. Daily actions drive the engine. We are what we repeatedly do.

4. Active listening is a martial art.
As Colum at CoachEm says, curiosity is the currency that unlocks trust.

5. Feedback is love.
Frequent, honest feedback isn’t a luxury—it's oxygen for growth. (Thanks to Dr. Rachel Pacheco for the unforgettable underwear analogy. 😅)

6. Transparency and vulnerability are superpowers.
Admit mistakes. Wear your struggles. Trust follows authenticity.

7. Master the basics before getting fancy.
Tech is a tool, not a crutch. Fundamentals win championships.

8. Coach to the career, not the quarter.
Short-term wins are great, but long-term investment in your people pays compounding dividends.

9. Embrace AI or get left behind.
AI won’t replace salespeople. It will replace those who don’t use it.

10. Don’t rush to solutions.
Sales is like a carwash—the rinse cycle (discovery) is crucial. Skip it, and the dirt stays.

🔥 Every guest brought their A-game this year, and 2025 is already shaping up to be NEXT LEVEL. We’re kicking off with sales leaders from Zoom and Sysdig to answer the big questions:

• What makes a great sales leader?
• How do you create buy-in without being a dictator?
• How do you hold yourself (and your team) accountable?

Your voice matters. Keep the feedback, guest ideas, and tough questions coming.

Coaching isn’t a checkbox. It’s a craft, a mindset, and the only sustainable way to build teams that thrive. If you’re not coaching them, you’re losing them.

Here’s to an even stronger 2025.

Happy Holidays, and see you next year!

#SalesLeadership #CoachingCulture #EndOfYearReflections #CoachTheScale

What if your beliefs about feedback and coaching timelines are holding you back? Guest host Colum Lundt, CEO of CoachEm, takes the helm to interview our regular host, Matt Benelli! Both are co-founders of CoachEm and share the myths and misconceptions about coaching sales teams. Matt dismantles the notion that coaching yields immediate results, likening this misconception to expecting instant mastery in swimming. They advocate for feedback that strikes a balance, highlighting strengths while pinpointing areas for improvement, and the power of self-assessment that transforms coaching into a nurturing ground for growth.

Navigating the murky waters of management can be daunting for new leaders. Our discussion uncovers the universal struggle of setting expectations and the weight of maintaining accountability within teams. Through candid anecdotes, they uncover why some managers shy away from difficult conversations and the all-too-common trap of wanting to be liked. By modeling self-accountability and utilizing strategies like setting clear goals, holding regular one-on-one meetings, and providing timely feedback, managers can foster an environment of responsibility and success within their teams.

Finally, Matt explores the art of leadership through preparation and engagement. We highlight how leaders like Mike Myers and Bill Belichick exemplify humility, discipline, and adherence to team values. These seasoned mentors teach us the importance of thorough preparation, the strategic use of "commander's intent," and conveying messages from higher-ups in an inspiring way. Matt reflects on how building a team around shared values paves the way for long-term success.

Chapters:
(00:00) Building Coaching Cultures
(15:27) Accountability and Effective Management Strategies
(31:48) Effective Leadership Lessons Learned
(43:32) Coaching Lessons and Leadership Attributes

Takeaways:

• Long-term Investment in Coaching: Sales coaching is not about immediate results. It's a long-term investment in behavior change, similar to learning a new skill. Sales leaders should approach coaching with patience and commitment, focusing on gradual improvement over time.
• Balanced Feedback: Effective feedback should be balanced, highlighting both strengths and areas for improvement. Encouraging self-assessment among team members can create a more constructive and positive coaching environment, promoting growth and development.
• Accountability and Modeling Behavior: Sales leaders must hold themselves accountable before they can effectively hold their teams accountable. Modeling the behavior they wish to see in their teams is crucial for setting clear expectations and maintaining accountability.
• Structured Management Strategies: Implement structured strategies such as setting clear goals, tracking progress, and providing timely feedback. Address underperformance immediately to prevent issues from escalating, and maintain regular one-on-one meetings to reinforce accountability.
• Leadership Beyond Directing: Leadership involves preparation, engagement, and composure under pressure. Convey motivational messages effectively and focus on building inclusive environments. Use the "commander's intent" concept to guide teams towards common objectives.
• Learning from Notable Leaders: Emphasize humility, positivity, and adherence to team values as demonstrated by leaders like Mike Myers and Bill Belichick. Investing in managerial training and focusing on shared team values can lead to long-term success.
• Commitment to Self-Development and Curiosity: Encourage a commitment to self-development and foster a culture of curiosity within the team. These traits can be developed and are essential for continuous improvement and effective leadership.
• Effective One-on-One Meetings: Maintain the importance of one-on-one meetings with team members. Consistently holding these meetings demonstrates care for team members' success and fosters a culture of accountability and feedback.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

What if everything you thought you knew about leadership was turned on its head? Join us for an enlightening conversation with J.D. Sillion, a two-time CEO and three-time CRO, as he dissects the myths surrounding leadership and unveils a powerful framework for guiding teams through both high-growth and turnaround situations. Drawing inspiration from sports legends like Phil Jackson, J.D. emphasizes nurturing potential over wielding authority to foster an environment where teams can thrive. Our discussion traverses the challenges of sales accountability and the critical roles of strategy, structure, and culture in achieving team success.

Imagine a sales process so efficient that each deal feels like a win for your entire organization. J.D. Sillion discusses the pitfalls of low win rates and their impact on morale and scalability, advocating for a culture of accountability. But what does it mean to truly empower autonomy within your team? J.D. explores the nuances between kindness and niceness, emphasizing the need for honest conversations that help team members grow. Learn about the success contract framework and how maintaining high standards can transform your organization and align teams with a shared mission.

Reflecting on personal growth and the mentors who shape us, JD shares stories from his own journey, highlighting influential figures like Lisa Gallagher and Sal Sylvester. Through personal anecdotes, JD reveals how overcoming ego and embracing continuous learning can lead to profound transformation. Whether it's climbing metaphorical peaks in business or contemplating the art of giving a TED Talk, J.D.’s insights are a masterclass in leadership. As we wrap up, listeners are left inspired to challenge the status quo, driven by the insights of thought leaders such as Greg Popovich, Jim Collins, and Marshall Goldsmith.

Chapters:
(00:00) Building a Culture of Winning
(12:16) Achieving Sales Accountability and Empowering Autonomy
(27:26) Leadership Lessons for Success
(34:39) Continuous Transformation in Business and Sales
(41:56) Navigating Leadership and Coaches

Takeaways:

• Visionary Leadership and Team Success: JD emphasizes the importance of creating a compelling vision and fostering an environment that nurtures potential. CROs should focus on building a culture that supports team success rather than relying on authority or outperforming team members.
• Strategic Framework for Transformation: JD introduces a strategic framework centered on strategy, structure, and culture. CROs can use this framework to guide their organizations through high-growth and turnaround scenarios, ensuring alignment with a clear vision and purpose.
• Sales Accountability and Targeting: It is crucial for CROs to ensure sales accountability and target the right audience to enhance success rates. Focusing on product-market fit and maintaining high standards will boost win rates and morale within the sales team.
• The Importance of Difficult Conversations: True leadership involves having honest conversations that drive improvement and growth. CROs should distinguish between being kind and being nice, where kindness means caring enough to engage in challenging dialogues for the benefit of the team.
• Continuous Learning and Adaptation: JD underscores the value of continuous learning and adapting to new challenges, likening business obstacles to scaling Mount Everest. CROs should encourage a culture of perseverance, improvement, and embracing feedback.
• Role of Mentorship: Mentors and coaches play a vital role in shaping leadership journeys. CROs should seek guidance from influential figures to transform their leadership styles and inspire their teams.
• Autonomy and Accountability: Autonomy should be earned through accountability. CROs need to establish clear, non-negotiable KPIs and regularly review performance to foster a culture of responsibility and excellence.
• Global Perspective: For CROs leading international teams, understanding cultural nuances and decision-making processes is essential. Tailoring leadership and sales strategies to fit diverse cultural contexts can significantly enhance global business operations.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Keith Rabkin, the Chief Revenue Officer at PandaDoc, takes us on a journey through his unconventional path to sales leadership, revealing a fresh perspective on motivating sales teams that challenges the age-old myth of money being the sole motivator. Keith unpacks the art of understanding individual aspirations and leveraging them to enhance performance through his innovative two-by-three matrix approach. With an emphasis on setting personal goals and addressing team development needs, Keith provides actionable strategies for leaders committed to cultivating a robust coaching environment that inspires.

We rethink the sales process as a collective endeavor rather than a solitary pursuit, emphasizing the benefits of a customer-centric approach. Keith and I uncover the perils of the lone wolf mentality and highlight how collaboration and teamwork can elevate both sales outcomes and customer satisfaction. By involving multiple team members and building trust, sales professionals can foster long-term relationships that lead to repeat business and larger deals, proving that sales truly is a team sport.

Adapting to change in the sales landscape is no small feat, yet Keith shares his experiences and insights from the transition to value selling at PandaDoc. Drawing from the book "Switch" by Chip and Dan Heath, we discuss the role of enablement teams and consistent messaging in facilitating this shift. Keith’s reflections on mentorship and leadership reveal the importance of honest conversations, personal growth, and effective coaching in creating resilient and successful sales teams. Through his journey, Keith exemplifies how a focus on customer-centric values and strong mentorship can shape impactful leaders.

Chapters: 

• (00:00) - Modern Sales Leadership
• (10:31) - Sales as a Team Sport
• (13:52) - Navigating Difficult Conversations in Leadership
• (18:52) - Adapting to Change in Sales
• (33:23) - Coaching Influence on Leadership Success
• (36:34) - Coaching and Talent Development Strategies

Takeaways:

• Sales leadership is not solely about financial incentives. Keith Rabkin emphasizes understanding individual motivations beyond monetary goals. He introduces a structured two-by-three matrix framework to help leaders align personal aspirations with organizational needs, creating a more effective coaching environment.
• Sales should be approached as a collaborative, customer-centric effort rather than a solitary endeavor. Keith highlights the drawbacks of the lone wolf mentality and underscores the benefits of teamwork in building trust, improving close rates, and increasing deal sizes.
• Difficult conversations are crucial in sales leadership. Keith discusses the importance of honesty, data-driven feedback, and planning in managing expectations and improving team dynamics. These conversations, when handled well, foster transparency and opportunities for growth.
• Transitioning to value selling requires consistent reinforcement and support from enablement teams and managers. Keith shares insights on overcoming comfort zones and emphasizes the importance of repetition and planning in implementing change effectively.
• Mentorship plays a significant role in shaping effective leaders. Keith reflects on his career growth at PandaDoc, influenced by mentorship from industry leaders, and how a focus on customer-centric values can drive success and innovation.
• Effective coaching and leadership involve pushing team members to grow and excel. Drawing parallels to sports coaching, Keith emphasizes the importance of recruiting resilient individuals and fostering a challenging environment to promote critical thinking and development.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

In today’s episode, Matt interviews Ed Diller, Sales Leader at New Relic. They explore effective coaching practices and myths in sales leadership. They discuss the importance of strategic communication, creating win-win scenarios, and maintaining work-life balance in a post-COVID world. Ed shares valuable lessons from his extensive career, emphasizing the need for risk-taking, clear communication, and the benefits of focusing on strengths. He also highlights the role of coaching in career progression and how leaders can foster engagement and avoid burnout in hybrid work environments.

Takeaways:

• Ensure clear and concise communication, especially when working remotely. Utilize tools to mitigate grammatical errors and enhance the professionalism of communications.
• Use virtual face-to-face meetings (via Zoom or similar platforms) to maintain human connection and engagement within the team. Promote informal interactions to build camaraderie.
• Focus on being invited to higher-level discussions rather than bypassing immediate contacts. Build rapport and trust with initial points of contact before aiming for discussions with their superiors.
• Address the need for work-life balance in a remote work environment to prevent burnout among team members.
• Recommend that aspiring sales leaders read beyond typical sales books, exploring works that provide broader insights into leadership, strategy, and empathy.
• Focus on modeling the behaviors and strategies you want to see in your team. Provide constructive feedback aligned with their career aspirations, not just their current roles.

Quote of the Show:

• “Great salespeople don't just want a bigger paycheck for selling more. They want to take on more, they want to do more.” - Ed Diller

Links:

• LinkedIn: https://www.linkedin.com/in/edwardmdiller/ 
• Website: https://newrelic.com/ 

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Today, Matt discusses the significance of building coaching cultures with sales leader Derek Bates, VP of Northeast Sales at Alteryx. They delve into the myths of sales coaching, the importance of efficiency and work-life balance, and Derek's unique 3-P (People, Process, Performance) framework. Derek shares insights from his extensive career at Oracle and how he has applied those experiences at Alteryx. Additionally, they touch on personal stories, including Derek's college baseball coach's influence, the role of leadership in retaining talent, and strategies for effective time management.

Takeaways:

• Recognize that money isn't the only motivator. Salespeople are complex, and good leaders need to understand what truly drives their team members beyond just their compensation.
• Encourage discipline and efficiency to maintain a healthy work-life balance. Overworking should not be glorified; find ways to help your team manage their time effectively.
• Tailor your coaching approach to the individual needs of each team member. Every person is different; understanding their unique triggers and motivational factors will help you coach them more effectively.
• Hire and build teams with a diversity of thought. Different perspectives can lead to innovative solutions and a more dynamic team environment.
• Teach and practice strong time-management skills. Block off dedicated time for key activities like prospecting to maintain a steady pipeline and avoid the rollercoaster effect in performance.
• Develop and refine processes that support your team but allow their creativity to shine with customers. A good process should eliminate internal inefficiencies.
• Teach your team to look at the bigger picture in their deals and accounts. Hitting short-term targets is important, but building sustainable long-term relationships with clients is essential.

Quote of the Show:

• “Not everybody works like you, otherwise they would be in your role.” - Derek Bates

Links:

• LinkedIn: https://www.linkedin.com/in/derek-bates-a14a7720/ 
• Website: https://www.alteryx.com/ 

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

In this episode of Coach2Scale, Matt Benelli sits down with Mark Roberge, the founding CRO of HubSpot and the Co-Founder of Stage2 Capital. They discuss innovative approaches to sales coaching, including the importance of focusing on the percentage of reps hitting quota and why new reps should not shadow top performers. Mark shares insights on proactive coaching methods and the significance of data in diagnosing sales issues. They also talk about Stage 2 Capital, a fund that leverages the expertise of top sales and marketing leaders to guide startups. This conversation is a must-listen for anyone involved in sales leadership, exploring effective coaching techniques and the science of scaling revenue.

Takeaways:

• Prioritize the percentage of reps hitting quota over overall team attainment to get a true sense of team health and sustainability.
• Avoid having new reps shadow top performers due to potential bad habits and lack of universal applicability in their methods. Instead, create a standardized sales process that codifies best practices.
• Develop a systematic approach to coaching by holding regular one-on-one sessions where managers diagnose and address specific performance issues with each rep, using data to guide the coaching process.
• Use metrics to evaluate the effectiveness of coaching, such as tracking improvements in specific areas like opportunity funnel conversion rates.
• Design processes that force managers to be proactive, such as monthly or quarterly reviews that focus on qualitative and quantitative performance assessments.
• Select potential managers based not just on their sales performance but on their leadership abilities and coaching potential. Consider the different skill sets required for managing and selling.
• Develop training programs that help reps learn to self-diagnose their performance issues, fostering independence and continuous improvement.

Quote of the Show: 

• “A great rep doesn’t have to wait till the monthly or the quarterly review or the next chat with the managers. They can reflect and they almost can self-diagnose mid-meeting.” - Mark Roberge

Links:

• LinkedIn: https://www.linkedin.com/in/markroberge/ 
• Website: https://www.stage2.capital/ 
• Book: https://www.amazon.com/Sales-Acceleration-Formula-Technology-Inbound/dp/1119047072/ref=sr_1_1?adgrpid=1343603773753404&dib=eyJ2IjoiMSJ9.HRz6Z9-h6Fs_mYwBMgiU0-foFhPZk7lV1Y_-t8l-nzMDqpScpOw4nmQ_rYxPA1wcnpX3TBFyb8yNpSzjlVTs59n_PTI8-NNIEgP19eSWNT1KTmXw4bM-Ik1ON3bbLvRpNl5MzAe1p06iMnrZbZx8kDWOUuQgr-pQuENmlU-h-Q6xc4J6ediHpdD_5Lsji4ppITe9CHQf52MHPix2VP3jV2_TAuJrp94U-1HkqjU0-jA.pWGGm1VSdrsIGa-hXJX--Sl-r0tIg3TZy93Ed_nAf98&dib_tag=se&hvadid=83975476617453&hvbmt=be&hvdev=c&hvlocphy=104857&hvnetw=o&hvqmt=e&hvtargid=kwd-83975581283309%3Aloc-190&hydadcr=21931_13325420&keywords=the+sales+acceleration+formula&qid=1731013960&sr=8-1 

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

In this episode of Coach2Scale, Matt speaks with Pat Deskin, Chief Revenue Officer at NewStore, to debunk the myth that senior sales reps don't need coaching. Pat emphasizes the importance of consistent one-on-ones, urgency in sales, and the integration of people and process to scale companies successfully. The discussion also explores Pat's influential experiences and favorite coaching philosophies from Vince Lombardi. 

Takeaways:

• Ensure that even your most experienced reps receive consistent coaching. Coaching should be part of the regular routine, helping them to continually evolve and improve.
• Implement a structured one-on-one meeting framework that includes consistent questions like "What did you do differently this week?" and covers key aspects like forecast, key deals, pipeline, and help needed.
• Dedicate the last one-on-one of each month to discussing personal development, career aspirations, and any struggles. Keep this separate from business discussions to humanize the interaction.
• Encourage your team to act quickly and not delay responses or actions. Immediate responses, even on weekends or nights, can make a significant difference in client relationships and deal success.
• Hire and promote individuals who demonstrate curiosity and problem-solving skills. These traits are essential for tackling both internal and external challenges.
• Create a competitive yet collaborative environment where team members are held accountable.
• Break down complex processes into simple, clear elements. This makes them easier to follow and ensure everyone is on the same page, similar to Vince Lombardi's approach.

Quote of the Show:

• “A play doesn't run really well unless everybody's on the same page and there's a leader who's demanding excellence at all time.” - Pat Deskin

Links:

• LinkedIn: https://www.linkedin.com/in/patrickdeskin/ 
• Website: https://www.newstore.com/ 

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

In this episode of Coach2Scale, Matt Benelli engages in a thought-provoking conversation with Jill Harris, VP of Sales for North America at GoTo. Jill shares her insight on balancing empathy and accountability in sales coaching. She emphasizes the importance of asking the right questions and fostering a collaborative environment when it comes to sales leadership. Jill introduces her Sales Coaching Plan, which focuses on co-creating solutions and addresses the root causes of underperformance. The episode discusses fostering self-awareness and accountability among reps, navigating the risks of an excuse culture, and maintaining a growth mindset amidst change.

Takeaways:

• Understand that empathy is essential, but it should not replace accountability. Balance both to create effective and compassionate leadership.
• Focus on asking insightful questions rather than having all the answers. This approach allows sales reps to self-identify areas for improvement.
• Develop performance and development plans together with your sales reps. This ensures engagement and ownership from both sides.
• Develop a structured coaching framework that includes sales skills, product knowledge, and operational metrics.
• Encourage a growth mindset within your team. Frame challenges as opportunities for development rather than insurmountable obstacles.
• Build trust with your team by actively listening to their concerns and providing thoughtful feedback. 
• Acknowledge that change is constant and prepare your team to adapt. Mentally and structurally prepare for inevitable industry shifts.

Quote of the Show:

• “The best coaches are those that are fantastic listeners, they ask so many good questions. They essentially peel back the onion where they're helping the coachee to come to their own conclusions.” - Jill Harris

Links:

• LinkedIn: https://www.linkedin.com/in/jill-harris-549b052/ 
• Website: https://www.linkedin.com/in/jill-harris-549b052/ 

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale 

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io

Today host Matt Benelli engages in a thought-provoking conversation with sales leader Steve Boss. The discussion spans a variety of topics, including effective sales coaching, the challenges of transitioning to management, and the importance of self-advocacy and mentorship. Highlighting the significance of managing both up and down within an organization, the episode provides practical advice on being solution-oriented and proactive. Steve emphasizes the vital role of authenticity, empathy, and individualized communication in leadership. The two also explore the transformative potential of AI in sales, illustrating how technology can enhance efficiency and effectiveness.

Takeaways:

• Start taking on the responsibilities of the job you want before it becomes available. This demonstrates your capability and preparedness for the next role.
• Be the same person at work as you are at home. Authenticity fosters trust and stronger relationships with your team.
• Recognize the individuality of each team member and tailor your coaching to fit their unique needs and stages in their careers.
• Encourage team members to take the lead on projects and responsibilities. This not only empowers them but also prepares them for future leadership roles.
• Be constructively discontent. Recognize issues in the organization but always frame them with solutions that align with overall company goals.
• Always bring a point of view and a solution when presenting issues to upper management. This helps in being seen as a problem-solver rather than a complainer.
• Seek mentors who have your best interests at heart and can offer unbiased advice.

Quote of the Show:

• “Nothing's going to happen for you in this corporate world just because you think you deserve it. You got to get up every day, you got to work hard, you got to prove it.” - Steve Boss

Links:

• LinkedIn: https://www.linkedin.com/in/bosssteve/ 

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU 
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 
• YouTube: https://www.youtube.com/@Coach2Scale

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward.  These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io