Surviving Sales Leadership – Details, episodes & analysis

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Surviving Sales Leadership

MySalesCoach

Business

Frequency: 1 episode/17d. Total Eps: 11

Sales leaders! Want to build strong teams without burning out in the process? Introducing Surviving Sales Leadership, where each episode is a practical conversation with experienced sales leaders and elite sales coaches about what actually works. Coaching reps, managing pipeline, forecasting, enablement, and navigating growth without everything feeling harder than it should. No “just hold people accountable” nonsense. Real-world tactics and strategies that work in sales right now. If you’re a sales manager, head of sales, sales director, or revenue leader who wants better results, better conversations with your team, and a little more confidence in the chaos, this show’s for you. Subscribe and start surviving sales leadership today!

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Apple Podcasts

🇬🇧 Great Britain - management
24/08/2026
#74
🇨🇦 Canada - management
19/08/2026
#86
🇬🇧 Great Britain - management
30/05/2026
#90
🇬🇧 Great Britain - management
17/04/2026
#92

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https://www.linkedin.com/in/justwillaitken/
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https://www.linkedin.com/in/tom-boston/
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https://www.linkedin.com/in/nkapur/
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Score global : 63%

Publication history

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The Comp Plan Mistakes That Push Good Reps Out

Episode 7

Thursday, April 9, 2026 • Duration 35:16

Simple comp plans are easy to explain. Bad comp plans are easy to regret.

This episode gets into the real damage sales leaders create when compensation becomes unclear, unfair, too clever, or easy to game.

Want to be a great coach for your team and drive results in the time you DO have for coaching?
Download the Modern Revenue Leader's Sales Coaching Manual

In this sales leadership lesson, Mike Pritchett of BuzzTrail and David Wilkins unpack what actually happens when comp plans drift away from the behaviours the business needs.

Reps disengage fast when they cannot clearly see how they make money
Changing comp after overachievement destroys trust and pushes good people out
Complex plans create confusion, politics, and arguments over who deserves what
Poorly designed incentives drive sandbagging, bad meetings, gaming, and low-value activity
Too much disparity across reps creates distraction, resentment, and “why are they getting more than me?” conversations
Team-based targets can hide poor performance and pull everyone toward mediocrity
Commission-only setups sound attractive in startups, but make it harder to judge fit and build real team energy
Small non-cash rewards can sometimes motivate better than taxed cash incentives
Public recognition, competition, and simple scoreboards still matter because sales is hard and momentum matters

The core message is straightforward: compensation is not just about paying people. It shapes behaviour, trust, culture, focus, and performance. When leaders get it wrong, they do not just create payroll problems. They create distraction, resentment, short-term thinking, and a sales team that starts working the plan instead of working the market.

This episode is for VPs of Sales, Heads of Sales, SDR leaders, and founders trying to build comp plans that stay simple, reward the right actions, reduce internal friction, and help good reps perform without creating avoidable chaos.

(00:00) - Start

Timestamps

00:00 Why simple comp plans outperform clever ones

08:35 The hidden damage of changing comp mid-year

16:42 Incentivising the wrong behaviour and how reps game the system

27:18 SDR and AE comp, quotas, territory fairness, and startup trade-offs

39:46 Why communal targets and uneven comp create resentment

48:58 Non-financial rewards, surprise incentives, and recognition that actually lands

Brought to you by MySalesCoach.

Learn more about how we support leaders in building elite and consistent sales teams:

www.mysalescoach.com

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How To Build a High Performing Sales Team In The Chaos of SaaS

Episode 5

Wednesday, March 25, 2026 • Duration 38:56

Everything feels like it’s moving—and nothing feels stable.

You’re expected to build a high-performing team while the ground keeps shifting beneath you.

Want to be a great coach for your team and drive results in the time you DO have for coaching?
Download the Modern Revenue Leader's Sales Coaching Manual

In this episode, Tom Boston and Emily Parker break down what it actually looks like to build and lead a sales team inside the chaos of SaaS—where strategy changes, expectations evolve, and pressure never lets up.

This episode is for:

Sales leaders who are building or scaling teams in fast-moving environments, dealing with inconsistent performance, struggling with hiring decisions, or trying to maintain control and morale while everything around them changes.

Inside this sales leadership lesson:

Feeling like you’ve “figured it out”… only for messaging, ICP, or strategy to change overnight
Trying to lead with confidence when you’re figuring things out in real time yourself
Translating top-down strategy into something your team actually understands and buys into
Hiring people who look great on paper but can’t adapt when the environment shifts
Managing high performers who resist structure and think results excuse behaviour
Dealing with promotion pressure from reps who think they’re ready—but aren’t
Keeping morale high when growth is messy, processes are broken, and support is limited
Carrying extra roles (ops, enablement, HR) while still being accountable for performance
Balancing autonomy with accountability without losing control of the team
Building a team that complements each other—not just a group of similar performers

00:00 – Why building a sales team in SaaS still feels chaotic

What Top Sales Leaders Do Differently

Episode 4

Thursday, March 12, 2026 • Duration 38:54

Many sales managers focus on pipeline, activity, and numbers.

Top sales leaders focus on developing people.

Want to be a great coach for your team and drive results in the time you DO have for coaching?
Download the Modern Revenue Leader's Sales Coaching Manual

In this episode, Tom Boston sits down with Nia Woodhouse and Ollie Sharpe to explore the leadership behaviours, coaching habits, and decision-making that separate average sales management from truly high-performing sales leadership.

The conversation looks at how elite sales leaders structure coaching, build hiring processes, and create environments where reps consistently improve. Nia and Ollie explain why the best leaders separate performance management from skill development, ensuring that coaching sessions focus on mindset, skills, and long-term capability — not just forecast discussions.

They also break down how top leaders set goals that are actually achievable by reverse engineering revenue targets into specific activity and performance milestones. Instead of chasing a big number without direction, great sales leaders help their teams build a clear roadmap that shows exactly how success will be achieved.

The episode also explores hiring philosophy, emotional intelligence in leadership, and why the best leaders create trust by standing in front of their team when things go wrong — and standing behind them when they succeed.

This episode is essential listening for VPs of Sales, Heads of Sales, Sales Managers, and Revenue Leaders who want to move beyond activity management and build teams that consistently perform, grow, and stay motivated.

Why Your Deals Aren’t Closing: The Gaps Reps Won’t Tell You (Until You Coach Differently)

Episode 3

Wednesday, February 4, 2026 • Duration 24:26

If deals keep stalling and the story is always “they’ve gone quiet,” the real issue usually showed up much earlier — and it often isn’t being said clearly in coaching.

PS.
Want to be a great coach for your team and drive results in the time you DO have for coaching?
Download the Modern Revenue Leader's Sales Coaching Manual

This session with Steve Myers and Richard Smith gets into the actual reasons deals don’t close, and how deal coaching can surface the truth without turning into a forecast grilling.

We break down how to diagnose what’s missing in the deal, validate what’s real vs assumed, and coach reps beyond surface-level reasons into compelling, evidence-backed buying drivers.

This is for you if you're a sales leader dealing with:

“Close” deals that never close and pipelines full of hope instead of proof
Reps who can’t clearly articulate why a prospect will actually buy
Stalled opportunities where next steps were never properly locked in
A coaching culture where people tell you what sounds good, not what’s true

In this episode, you’ll hear the deal-killers hiding in plain sight:

Reps mistaking “they want X” for a real problem worth solving
“I think…” language replacing evidence — and nobody challenging it properly
Surface-level pain (“save time,” “be more efficient”) with no detail behind it
Discovery that never gets to the full three levels of pain: symptom → business impact → how people feel about it
No clear understanding of where budget comes from, how the decision gets made, or where veto power sits
Leaders accepting the rep’s narrative without validating what’s actually happened
Weak upfront contracting — so next steps aren’t agreed, meetings aren’t booked, and deals drift into silence

The Sales Coaching Disconnect No One Wants to Admit

Episode 2

Wednesday, January 14, 2026 • Duration 30:00

Sales leaders believe they’re coaching more than ever.

Sales reps are saying the opposite.

Download The State of Sales Coaching in 2026 Report here

In this episode, Tom Boston sits with Kevin Beales (Founder & CEO at MySalesCoach) and Richard Smith (Head of Growth at MySalesCoach) to unpack the State of Sales Coaching in 2026 and the uncomfortable disconnect between sales leaders’ intentions and reps’ lived experience. Drawing on real data from sales leaders and sales reps, we explore why coaching feels broken, why AI hasn’t fixed it, and what actually drives quota attainment in today’s sales environment.

We cover why tenured reps want more coaching (not less), how pipeline reviews are being mistaken for coaching, why weekly coaching dramatically increases quota attainment, and why human coaching still outperforms AI-only approaches when it comes to mindset, behaviour, and long-term performance.

This episode is essential listening for VPs of Sales, Heads of Sales, Sales Managers, and Revenue Leaders who want to build a true coaching culture - not just survive this quarter.

Want to be a great coach for your team and drive results in the time you DO have for coaching?
Download the Modern Revenue Leader's Sales Coaching Manual

Brought to you by MySalesCoach. Learn more about how we support leaders in building elite and consistent sales teams:
www.mysalescoach.com

Surviving Sales Leadership - Trailer

Episode 1

Monday, January 12, 2026 • Duration 00:47

Sales leaders! Want to build strong teams without burning out in the process?

Introducing Surviving Sales Leadership, where each episode is a practical conversation with experienced sales leaders and elite sales coaches about what actually works.

Coaching reps, managing pipeline, forecasting, enablement, and navigating growth without everything feeling harder than it should.

No “just hold people accountable” nonsense.
Real-world tactics and strategies that work in sales right now.

If you’re a sales manager, head of sales, sales director, or revenue leader who wants better results, better conversations with your team, and a little more confidence in the chaos, this show’s for you.

Subscribe and start surviving sales leadership today!

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How Sales Leaders Are Using LinkedIn to Build Their Own SQL Machine

Episode 10

Thursday, May 28, 2026 • Duration 36:43

Most sales leaders treat LinkedIn as a brand exercise. Post a few times a week, get some likes from colleagues, move on. But the reps who are actually self-sourcing pipeline are using it completely differently - they're building their own SQL machine, turning engagement signals into warm conversations before they even pick up the phone.

📥 Download the Modern Revenue Leader's Sales Coaching Manual https://bit.ly/3QTbqsJ

Will Aitken built his entire outbound motion around LinkedIn across three different companies. Niraj Kapur has done 220+ videos and converts inquiries directly from them. Between them and host Tom Boston, there are over 170,000 LinkedIn followers on this episode.

In this episode, Will and Niraj sit down with our host Tom Boston to get into what that actually looks like in practice - the content strategy, the video outreach, and the personal vs professional balance that most reps get wrong.

In this episode:

Why LinkedIn personal brand is an MQL list you build yourself - and take with you when you leave
How Will uses LinkedIn content to warm up prospects already in his pipeline between stages
Niraj's video outreach approach that generates direct inquiries and how he converts them
The 80/20 rule for personal vs professional content and what happens when you get it wrong
Why the algorithm matters far less than most people think
How to use LinkedIn strategically for named accounts, not just broadcasting to the masses
The one question to ask before posting anything: would your CEO share this?

About Surviving Sales Leadership:
Surviving Sales Leadership sessions help sales leaders tackle their biggest sales challenges in short, focused bursts - we aim to get most episodes done in 30 minutes or less.

New episodes fortnight. Subscribe so you don't miss one.

🌐 Episode page:

The Questions You're Not Asking That Kill a Forecast in 5 Minutes

Episode 9

Thursday, May 14, 2026 • Duration 34:37

Most sales leaders have sat across from a rep who's fully convinced a deal is closing.
Champion engaged.
Proposal out.
Close date locked.
And they're wrong.

Richard Smith sits down with Chris Lingenfelter (VP Sales & CS, Level Up) and Nigel Arthur (former MD and SVP Sales, enterprise SaaS - now coach at MySalesCoach) to show exactly what separates pipeline from forecast - and how fast the difference becomes obvious when you ask the right questions.

They cover why emotion is the single biggest killer of forecast accuracy, what entry/exit criteria your CRM stages are probably missing, and why a rep who "feels really good" about a deal is a red flag, not a green light.

The session ends with a live deal review. Richard plays the rep. Nigel and Chris ask five questions.

The deal doesn't make the forecast.

Find out which questions did it.

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We Analysed 5117 Sales Coaching Calls - Here's Why Your Deals Are Stalling

Episode 8

Wednesday, April 22, 2026 • Duration 41:16

Want to be a great coach for your team and drive results in the time you DO have for coaching?
Download the Modern Revenue Leader's Sales Coaching Manual

---
About this episode:

Ever had that feeling where your pipeline looks busy… but nothing’s actually moving?
Yeah. Turns out, you’re not alone.

Sales leaders think stalled deals are a pipeline problem.

Sales reps are experiencing something very different.

In this episode, Ollie Whitfield sits down with Steve Myers, and John Richardson to unpack insights from analysing 5117 real sales coaching calls and what they reveal about why deals lose momentum.

The conversation exposes a gap between what salespeople ask for in coaching and what’s actually holding performance back.

While most conversations focus on pipeline, deal progression, and “tips and tricks,” the real blockers often sit deeper—in decision process clarity, mindset, and how sales teams think about control in the deal.

The episode explores why decision process dominates coaching conversations, why “closing” is often misunderstood, and how over-reliance on tactics masks underlying behavioural and mindset challenges.

It also highlights the disconnect between prospecting responsibility and pipeline ownership, and how this impacts quota attainment and sales velocity.

This episode is essential listening for: VPs of Sales, Heads of Sales, Sales Managers and Revenue Leaders who are trying to improve sales coaching effectiveness, increase deal velocity, and build a stronger coaching culture that goes beyond surface-level tactics.

Surviving Sales Leadership – Details, episodes & analysis

Podcast details

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Surviving Sales Leadership – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

Other4

LinkedIn4

RSS feed quality and score

Publication history

Latest published episodes

Similar podcasts and content

Related Shows Based on Content Similarities

Apple Podcasts

Spotify

Related Shows Based on Content Similarities

Other4

LinkedIn4