The High Performance Sales Leader – Details, episodes & analysis

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The High Performance Sales Leader

Pree Sarkar

Business

Frequency: 1 episode/16d. Total Eps: 47

"Actionable Insights from Inspiring Tech CROs & VPs" dives deep into the world of sales leadership within the dynamic technology sector.

Join us for 20-30 minute candid conversations with distinguished sales leaders—from nimble startups to global powerhouses—as they share their personal journeys, strategies, and secrets behind their remarkable results.

Whether you're an aspiring sales leader or a seasoned expert looking for fresh insights, this podcast offers a treasure trove of real-world wisdom, actionable takeaways, and lessons learned from the front lines of tech sales.

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🇬🇧 Great Britain - management
17/11/2025
#97
🇬🇧 Great Britain - management
27/10/2025
#64

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https://www.linkedin.com/in/preesarkar/
51 shares
https://www.linkedin.com/in/fcalle/
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Score global : 48%

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Ep 47: How Losing a $1M Deal Led to Achieving 29 President Clubs with Stephen Cottrell

Episode 47

Friday, August 15, 2025 • Duration 28:10

Ever felt like you were doing everything right in a deal, only to lose it and realize you were never truly in the game? Or wondered how some reps consistently hit President’s Club like it's just another checkbox?

Stephen Cottrell doesn’t just hit quota. He’s earned 29 President’s Club awards over a 35-year career, closed over $1B in sales, and done it all across 48 countries. But it didn’t start that way. From boiling noodles in a Boston shoebox apartment to getting outflanked by IBM on a $1M deal, Stephen learned the hard way that grit, curiosity, and a process-driven mindset aren’t optional, they’re survival.

This episode isn’t about polished one-liners or LinkedIn fluff. It’s about what actually works: why MEDDIC changed his career, how to build resilience before you build pipeline, and the real reason being liked isn't enough. If you’ve ever wondered what separates the good reps from the elite, Stephen lays it all out. No filter, no fluff.

Let’s get into it.

Connect with Stephen Cottrell:
👉LinkedIn: https://www.linkedin.com/in/cottrell/

Connect with The High Performance Sales Leader Host:
👉LinkedIn: https://www.linkedin.com/in/preesarkar/

Hiring or replacing someone in the next 90 days?

We partner with tech sales leaders who are time-poor and under-pressure, and introduce them to top performers without wasting time or risking average hires, so that they can build winning teams and careers.

Message pree@switchgears.io today!

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E46: $5M to $55M: Craig Harris’ ScaleUp Journey at Deputy

Wednesday, July 16, 2025 • Duration 32:18

I spoke with Craig Harris, former CEO at Plexus and COO at Deputy … he has been a key part of some of the most exciting scale-ups in Australia.

Here’s Craig’s story ….

For 25 years, I’ve helped tech companies build at pace. But one journey that stands out—because of what it gave me, taught me, and broke in me—was Deputy.

In four years, we scaled from $5M to $55M. We didn’t do it with smoke and mirrors. We did it with systems, sweat, and a few very sore lessons. I’ll walk you through the path we took to scale, the frameworks that held under pressure, and how we pivoted when COVID sideswiped the entire business.

Not the “forgot your keys again” kind of chaos—but the high-octane, VUCA-drenched kind where companies grow fast, systems break, and you have to lead anyway.

Let’s get into it.

Connect with Craig Harris:

LinkedIn: https://www.linkedin.com/in/craig-harris-au/

Connect with The High Performance Sales Leader Host:

LinkedIn: https://www.linkedin.com/in/preesarkar/

Message pree@switchgears.io today!

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E37: Scaling from $5M to $38M: The Unreasonable Path to Startup Success with Russell Evans

Monday, November 11, 2024 • Duration 31:49

Russell Evans, former CRO at Dubber, discussed his transition from large corporations to startups, highlighting Dubber's growth from $5 million to $38 million ARR in five years. Key drivers included partnerships with Cisco and Microsoft, the unified communications as a service (UCaaS) market's 18-22% annual growth, and a partner-only go-to-market strategy. Evans emphasised the importance of cultural fit, data-driven decision-making, and maintaining a high-energy, partner-centric approach. Challenges included building a global team and ensuring partners were genuinely aligned with Dubba's vision. Evans also stressed the need for unreasonable expectations and clear communication to manage stakeholder and investor expectations.

Episode Highlights:

Why Russell Left the Corporate Giants for a Startup Rollercoaster
Scaling from $5M to $38M ARR in Five Years
Partner-Centric Models are Not for the Faint-Hearted
Building a Global Team is Harder Than You Think
The Importance of Repeating Yourself—Endlessly
Why Hiring for Attitude is the Key to Success
The Secret Sauce to Partner Success
The FOLAD Factor: Fear of Looking Like a Dick
Building a Culture of Trust and Accountability
The Unreasonable Person Drives Change
Unreasonable Expectations are Key to Growth
Managing Investor Expectations is a Delicate Balancing Act

Connect with Russell Evans:

LinkedIn:https://www.linkedin.com/in/russell-evans/

Connect with The High Performance Sales Leader Host:

LinkedIn: https://www.linkedin.com/in/preesarkar/

E36: Fail Fast, Fail Forward: The Key to Thriving in High-Pressure Sales and Leadership with Alex Palmer

Monday, October 21, 2024 • Duration 33:02

In this episode, we sit down with Alex Palmer, SMB Manager - ANZ at Deel, a hyper-growth Pre-IPO SaaS company revolutionizing payroll and workplace mobility worldwide. Originally from the UK, Alex came to Australia with dreams of playing professional cricket. His experience as an athlete shaped his approach to leadership, emphasizing continuous improvement, resilience, and a focus on team growth. Today, he leads with transparency, honesty, and a passion for helping others succeed—both on his team and through his mentoring work with organizations like Rare Birds and Early Work.

Episode Highlights:

From Cricket to Tech Sales: A Journey of Serendipity
Why Team Sports Prepare You for Business (More Than You Think)
The Pivot to Tech Sales: A Lucky Break or a Calculated Move?
From Sales Rep to Leader: The Mental Shift
The Art of Building High-Performance Teams
How to Spot a Bar-Raiser in Your Team
Eating the Frog: Why Doing the Hardest Thing First Matters
Why Ownership Beats Talent Every Time
The Duck and Eagle Theory: Managing Different Types of Performers
Radical Candour: The Key to Authentic Leadership
Creating Psychological Safety in High-Pressure Sales Environments
Fail Fast, Fail Forward: Iteration is Everything

Connect with Alex Palmer:

LinkedIn: https://www.linkedin.com/in/alex-palmer/

Connect with The High Performance Sales Leader Host:

LinkedIn: https://www.linkedin.com/in/preesarkar/

E35: Video, Social Selling and Authentic Leadership Insights From The Front Lines with Mark Fazackerley

Monday, September 23, 2024 • Duration 24:32

In this episode, we explore the power of a beginner’s mindset with Mark Fazackerley, a high-performance sales leader and martial arts practitioner. Mark shares how adopting a sense of wonder can open up infinite possibilities, whether in business or personal growth. We also delve into his journey through martial arts, how it shaped his leadership style, and his unique perspective as the "Roving Reporter" on LinkedIn.

About Mark Fazackerley:

Mark Fazackerley, a high-performance sales leader who has made a significant impact across some of the most well-known companies in the industry, including Oracle, Talend, Qlik, and MicroStrategy. Mark is not only respected for his leadership and sales acumen but also for the authentic way he shows up in the world—a quality deeply influenced by his lifelong passion for martial arts.

Many of you may recognise Mark from his engaging LinkedIn Video posts as the ‘Roving Reporter,’ where he leads by example in the realm of social selling. In this episode, we’re going to dive deep into his journey, his philosophies on leadership, and how martial arts has shaped the way he connects with and inspires others.

Episode Highlights:

02:35 The Early Influence of Kung Fu
05:48 Karate as a Life-Changing Decision
07:30 Applying Martial Arts Discipline in Sales
08:46 Embracing the Beginner’s Mindset
12:16 The Importance of Situational Awareness in Sales
13:40 The Birth of the Roving Reporter: A Social Selling Experiment
15:36 Harnessing the Power of Video Content
17:00 Overcoming the Fear of Putting Yourself Out There
24:17 The Power of Authenticity in Leadership

Connect with Mark Fazackerley:

LinkedIn:https://www.linkedin.com/in/markfazackerley/

Connect with The High Performance Sales Leader Host:

LinkedIn: https://www.linkedin.com/in/preesarkar/

E34: Beyond the Hype: How AI is Transforming Business—and Why Human Touch is Key with Peter Sharples

Monday, September 9, 2024 • Duration 42:53

What has shaped your journey so far?

In this episode, we sit down with Peter Sharples, Vice President APAC at Builder.ai, a Series D unicorn revolutionizing the tech landscape through AI-driven app development. Peter, formerly with AWS, shares his journey from civil engineering to becoming a leader in the tech industry, highlighting the transformative shift from cloud computing to AI. He also reflects on the key decisions and experiences that have defined his career.

Episode Highlights:

The Journey Begins: Learning from Mistakes
The Power of Serendipity: When One Door Closes
Early Lessons: The Importance of Humility and Resilience
Embracing Change: Moving Beyond Comfort Zones
The Game Changer: Lessons from AWS
The Future is AI: Why I’m Betting on the Next Decade
Adapting to the New Normal: What the Future Holds

Connect with Peter Sharples:

LinkedIn: https://www.linkedin.com/in/petersharples/

Connect with The High Performance Sales Leader Host:

LinkedIn: https://www.linkedin.com/in/preesarkar/

Message pree@switchgears.io today!

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E33: Leading with Purpose: How to Navigate Uncertainty, Change and Growth with David Oakley

Monday, September 2, 2024 • Duration 37:56

In this episode, David Oakley shares his experiences transitioning from industry-leading giants like IBM and Oracle to working with innovative companies such as ServiceNow and Miro. He delves into the benefits of starting a career in large organizations and how those experiences shaped his approach in more agile, cutting-edge environments. Dave also discusses the importance of self-management, leadership, and creating a sustainable work environment that fosters long-term success.

Episode Highlights:

01:19 The Unplanned Path: From Big Names to High-Growth Startups

03:03 Learning from the Giants: The Benefits of Big Company Experience

04:13 Managing Yourself: The Foundation of Leadership

07:01 Playing the Long Game: Balancing Sprints with Sustainability

10:32 Building Cross-Functional Cohesion: The Power of Teaming

14:58 Leading with Purpose: Connecting the Dots for Your Team

20:39 Adapting Your Leadership Style: From Experience to Facilitation

32:24 Embracing AI: The Future of Sales Leadership

Connect with David Oakley:

LinkedIn: https://www.linkedin.com/in/oakleydavid/

Connect with The High Performance Sales Leader Host:

LinkedIn: https://www.linkedin.com/in/preesarkar/

E32: From Expectation to Achievement: How I Landed My Dream Sales Leadership Role with Kwame Aforo-Addo

Monday, August 26, 2024 • Duration 26:51

In the realm of personal and professional development, few stories capture the essence of persistence and determination quite like that of Kwame Aforo-Addo. A sales leader at UKG Software, a third-degree black belt, and a former regional-level 100-meter sprinter, Kwame’s journey is a testament to the power of unwavering commitment to one’s goals. His story is one that inspires not only his peers and colleagues but also those who are navigating the challenges of career transitions and personal growth.

Episode Highlights:

01:56 Meeting Kwame: The Unannounced Visit

05:32 The Power of Consistent Daily Action

07:49 Building Confidence Through Commitment

10:28 Overcoming Challenges During the Career Break

13:37 The Athlete’s Mindset: Training for Success

15:49 The Role of Mentorship and Networking

Connect with Kwame Aforo-Addo:

LinkedIn: https://www.linkedin.com/in/kwameaa/

Connect with The High Performance Sales Leader Host:

LinkedIn: https://www.linkedin.com/in/preesarkar/

Message pree@switchgears.io today!

E31: From AE to APAC Sales Director: Fail, Learn and Grow with Tanya Neary

Monday, August 5, 2024 • Duration 29:38

Tanya Neary, Senior Director of New Business APAC at Culture Amp, an Australian startup turned global SaaS player, has spent over a decade shaping and growing the company. Her journey is a rich tapestry of challenges, successes, and invaluable lessons. In this interview, Tanya shares her insights on growth, culture, and leadership.

Episode Highlights:

01:30 Tanya Neary's Visionary Journey

03:00 Identifying the Market Gap

07:13 Encouraging Innovation Through Failure

09:21 Nurturing a Strong Company Culture

11:05 Navigating Challenges with Resilience

15:39 Global Expansion Strategies

21:23 Embracing Change and Adaptability

Connect with Tanya Neary:

LinkedIn: https://www.linkedin.com/in/tanya-neary

Connect with The High Performance Sales Leader Host:

LinkedIn: https://www.linkedin.com/in/preesarkar/

Message pree@switchgears.io today!

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E30: Breaking Barriers: From HR to Sales Leadership with Emma Cahalane | Sales Leader ex Google/ DoorDash

Monday, July 22, 2024 • Duration 26:42

In today's episode, we're thrilled to have Emma Cahalane, a seasoned sales leader, sharing her invaluable insights and experiences. Emma's journey from HR to sales leadership has been nothing short of inspiring, and her expertise spans diverse sectors, including tech giants like Google and innovative startups like Sonder and DoorDash. She discusses prevalent gender dynamics in sales and offers strategies for fostering inclusivity and championing diversity, effective sales techniques, and many more.

Join us as we uncover the secrets to sales success.

Episode Highlights:

00:44 From HR to Sales: The Initial Leap

02:53 Overcoming Early Challenges in Sales

05:04 Gender Dynamics in the New Business Team

07:28 The Drive to Leadership

08:59 Leading Diversity Initiatives at Google

11:42 Addressing Challenges in Scaling Organisations

18:41 The Importance of Sponsorship and Retention

20:51 Creating an Environment for Progression

Connect with Emma Cahalane:

LinkedIn:https://www.linkedin.com/in/emmacahalane1/

Connect with The High Performance Sales Leader Host:

LinkedIn:

The High Performance Sales Leader – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

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The High Performance Sales Leader – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

LinkedIn31

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

LinkedIn31