The Sell Like A Leader Podcast

David Kreiger sits down with Denise Willett, Vice President of Sales at Coconut Software, which builds appointment, queuing, and video banking tools for financial institutions, and former CRO of Nest Wealth. Over the past year, Denise has been building AI agents hands-on for her own sales team, and in this episode she breaks down what it actually takes.

In this episode, they cover:

• What an AI agent is, and why a good prompt and a good agent solve different problems
• The two-day enablement format that had Coconut's sales and marketing teams building agents
• Why building the agent isn't the hard part, and the planning template Denise's team fills out before building anything
• How her team cut account planning from three hours to eight minutes
• Agents that surface next best actions and the accounts reps should focus on each week

If you feel like you should be building AI agents for your sales team but aren't sure where to start, this conversation gives you a practical place to begin.

Connect with Denise Willett:

https://www.linkedin.com/in/denisewillett/

https://www.coconutsoftware.com/

Connect with David Kreiger:

https://www.linkedin.com/in/davidkreiger/

https://salesroads.com/

Subscribe to the podcast and follow our Podcast LinkedIn page so you don't miss any episodes!

https://www.linkedin.com/company/sell-like-a-leader-podcast/

David Kreiger sits down with Donald C. Kelly, founder of The Sales Evangelist, one of the longest-running B2B sales podcasts in the world with nearly 2,000 episodes, and Chief Creative Officer of Blue Mango Studios, to break down exactly how a struggling seller becomes a closer.

In this episode, they cover:

• The role-play habit most reps avoid, and why it builds real muscle memory
• Why leaders should be the ones earning market trust before an SDR ever picks up the phone
• Why "the gift of gab" is the wrong explanation for who succeeds in sales, and what actually separates top performers
• How Donald used AI to reverse-engineer a competitor's client list into a hyper-targeted, FOMO-driven outreach campaign

If you're building or coaching a sales team and still think talent is the differentiator, this conversation will change your mind.

Connect with Donald C. Kelly:

https://www.linkedin.com/in/donaldckelly/

https://prospectpro.io/

Connect with David Kreiger:

https://www.linkedin.com/in/davidkreiger/

https://salesroads.com/

Subscribe to the podcast and follow our Podcast LinkedIn page so you don't miss any episodes!

https://www.linkedin.com/company/sell-like-a-leader-podcast/

David Kreiger sits down with Mark Roberge, Co-Founder and Managing Partner of Stage 2 Capital, founding CRO of HubSpot, and senior lecturer at Harvard Business School, to break down the three-step framework behind his new book, The Science of Scaling — a data-driven answer to the question most founders never rigorously address: when to scale.

In this episode, they cover:

• Why the metrics most founders use to "prove" product-market fit are actually the wrong ones
• The three-variable formula for building your own leading indicator of retention
• The real reason churn gets blamed on customer success and product, when the sales team is usually the root cause
• Why hiring in a "lump sum" after a fundraise breaks companies, and the pacing model Mark recommends instead
• Two moats built for the AI era: an AI-native org chart, and a "trust moat" in the vertical markets everyone else is ignoring

If you've told your board you're ready to scale without a defensible reason why, this conversation gives you the full framework to get one.

All proceeds from Mark's new book, The Science of Scaling, go to mental health research at McLean Hospital. Sell Like A Leader is giving away 15 copies — DM David Kreiger on LinkedIn to grab one.

Connect with Mark Roberge:

https://www.linkedin.com/in/markroberge/

Connect with David Kreiger:

https://www.linkedin.com/in/davidkreiger/

https://salesroads.com/

Subscribe to the podcast and follow our Podcast LinkedIn page so you don't miss any episodes! https://www.linkedin.com/company/sell-like-a-leader-podcast/

David Kreiger sits down with Justin Michael, creator of the Justin Michael Method and author of over 10 books, to explore why doing the opposite of what feels natural is the real key to winning in outbound.

His central premise is simple and uncomfortable: whatever thousands of sellers are doing right now is probably the wrong move.

In this episode, he breaks down:

• Why permission-based openers make buyers want to hang up
• How dating psychology explains why availability and neediness kill your pipeline
• The three walls every seller hits, and why most people never get past the first one
• How to build a semi-automated tech stack without losing the human edge that closes deals

If you're a sales leader still coaching your team on what feels safe, this conversation will change how you think about outbound entirely.

Connect with Justin Michael:

https://www.linkedin.com/in/michaeljustin/

Connect with David Kreiger:

https://www.linkedin.com/in/davidkreiger/

https://salesroads.com/

Subscribe to the podcast and follow our Podcast LinkedIn page so you don't miss any episodes!

https://www.linkedin.com/company/sell-like-a-leader-podcast/

David Kreiger sits down with Lynn Hidy, Founder of Up Your Telesales, to explore the most common mistakes inside sales leaders make and what it actually takes to build a team that performs consistently over time.

Lynn spent over two decades on the inside sales floor and made the unconventional choice to step back from management and stay a seller. That decision gave her a rare, ground-level view of what leadership gets wrong and what it takes to get it right.

In this episode, they cover:

• Why the skills that make a great individual contributor rarely transfer to leadership
• How redefining success inside a sales org keeps your best sellers doing what they're actually good at
• The bell curve reality that most leaders are ignoring
• The shift from product talk to problem talk, and how it makes your team less transactional almost overnight

If you're a sales leader trying to build a durable inside sales team without burning out your best people, this conversation will challenge how you think about promotions, performance, and coaching in 2026.

Connect with Lynn Hidy:

https://www.linkedin.com/in/lynnhidy/

Connect with David Kreiger:

https://www.linkedin.com/in/davidkreiger/

https://salesroads.com/

Subscribe to the podcast and follow our Podcast LinkedIn page so you don't miss any episodes!

https://www.linkedin.com/company/sell-like-a-leader-podcast/

David Kreiger sits down with Tom Stearns and Peter Cleary for a rare two-guest episode inspired by their newly released book, Graphic Sales: How to Build a Prospecting Playbook for Sales Leaders.

Together, they turned decades of real client work and hard-learned lessons into a sales book unlike any other.

In this episode, they cover:

• Why most sales leaders are misdiagnosing their biggest problem
• What a sales manager's day actually looks like once a real playbook is in place
• The evergreen fundamentals that have driven pipeline for decades and will still matter
• How the "Hell No" list transforms SDR performance, protects AE time, and stops your team from chasing wrong leads

If you're a revenue leader who's been putting out fires instead of building a system, this episode is for you.

And if you want to start applying these ideas right away, you don't have to wait for the episode to sink in. You can actually get your hands on the material behind it.

Download the first two chapters of Graphic Sales for free, along with the templates and tools behind the book here: https://www.stearns.io/

And if you want to go a level deeper, there are also paid kits available. Use code PODCAST for 30% off.

Connect with Tom Stearns:

https://www.linkedin.com/in/tomstearns/

Connect with Peter Cleary:

https://www.linkedin.com/in/peterecleary/

Connect with David Kreiger:

https://www.linkedin.com/in/davidkreiger/

https://salesroads.com/

Subscribe to the podcast and follow our Podcast LinkedIn page so you don't miss any episodes!

https://www.linkedin.com/company/sell-like-a-leader-podcast/

David Kreiger sits down with Jason Mironov of TA Associates to unpack how growth-focused investors evaluate sales organizations.

With over a decade of experience leading investments in tech-enabled services, Jason brings a rare "outside-in" lens to what revenue leaders must do to build an investment-ready business.

In this episode, he breaks down:

• Why gross vs. net retention tells the real story of your repeatability and why you should be tracking 10-15 key data points from day one
• Why spending an extra month upfront on sales education pays the biggest long-term dividends for rep productivity
• Why vibe coding your way into an enterprise customer base is a myth, and how AI is leveling the playing field for analytics
• What founders and revenue leaders should be building right now if they ever want institutional investment

If you're a revenue leader who wants to understand how world-class investors evaluate talent, culture, and the "direction of travel" for your revenue, this conversation is for you.

Connect with Jason Mironov:

https://www.linkedin.com/in/jmironov/

https://www.ta.com/

Connect with David Kreiger:

https://www.linkedin.com/in/davidkreiger/

https://salesroads.com/

Subscribe to the podcast and follow our Podcast LinkedIn page so you don't miss any episodes!

https://www.linkedin.com/company/sell-like-a-leader-podcast/

David Kreiger sits down with Aaron Ross, author of the bestselling Predictable Revenue, to revisit the principles that reshaped how the SaaS world thinks about sales, and examine what those principles mean in today's high-noise environment.

Aaron brings two decades of perspective on outbound, specialization, and pipeline building, and he challenges revenue leaders to stop chasing the playbook and start developing the instincts the current climate demands.

In this episode, he breaks down:

• Why the tactics from Predictable Revenue may have changed, but the core principles are more relevant than ever
• How AI is accelerating buyer attention fragmentation, and why ICP focus is now a non-negotiable
• The case for even deeper sales specialization as AI agents take on more of the SDR and AE workload
• Why the corporate world's hunger for stability is colliding head-on with a fundamentally non-linear era
• How emotional agility, intuition, and creativity are becoming the true competitive differentiators in sales leadership

Aaron's outside-in perspective will challenge how you think about building predictable revenue in 2026.

Connect with Aaron Ross:

https://www.linkedin.com/in/aaronross

Serendipity Sheet (new projects):

https://docs.google.com/document/d/1gCSfmPJRKzwl_1g2z5nxoEEOWDBAXojGglEUGU6yIp8/edit?pli=1&tab=t.0

www.freshair.substack.com

www.IronCrown.co

www.Delphi.ai/airzilla

http://www.fromimpossible.com/talk

Connect with David Kreiger:

https://www.linkedin.com/in/davidkreiger/

https://salesroads.com/

Subscribe to the podcast and follow our Podcast LinkedIn page so you don't miss any episodes!

https://www.linkedin.com/company/sell-like-a-leader-podcast/

David Kreiger sits down with Caryn Kopp, Chief Door Opener at Kopp Consulting, to explore why today's prospecting landscape is stacked against sellers, and what sales leaders need to do differently to break through.

Caryn brings a human-first philosophy to prospecting built on 27 years of opening C-suite doors, and she challenges some of the most common assumptions. In this episode, she breaks down:

• Why executive buyers ignore outreach that "feels" AI-generated
• How precision targeting and disciplined ICP selection outperform volume
• The structural shift sales leaders must make to build a predictable pipeline
• The difference between using AI for research vs. outsourcing your thinking
• Why prospecting requires a different DNA than closing, and why most AEs shouldn't own both

If you're a revenue leader trying to balance AI efficiency with real pipeline results, this conversation will challenge how you think about prospecting in 2026.

Connect with Caryn Kopp:

https://www.linkedin.com/in/carynkopp/

https://koppconsultingusa.com/

Connect with David Kreiger:

https://www.linkedin.com/in/davidkreiger/

https://salesroads.com/

Subscribe to the podcast and follow our Podcast LinkedIn page so you don't miss any episodes!

https://www.linkedin.com/company/sell-like-a-leader-podcast/

David Kreiger sits down with Chris Bondarenko, Chief Revenue Officer at 360 Learning, to explore what it really takes to build and scale high-performing revenue teams in today's rapidly evolving sales environment.

Chris brings a people-first approach to sales leadership that emphasizes the strategic importance of hiring the right personas, developing talent through continuous learning, and understanding where AI actually creates value versus where it falls short.

In this episode, he breaks down:

• Why top sales reps need to think like quarterbacks
• The three specific ways AI helps top performers win
• How to define clear success personas for each sales role and hire against these personas
• The two core revenue processes that must be clearly defined before any SaaS company can scale effectively

You'll also hear Chris's perspective on why people will always be the differentiator in sales, the dangers of rushing to automate without considering brand impact, and why leaders need more time to simply think about their business.

Connect with Chris Bondarenko:

https://www.linkedin.com/in/chrisbondarenko/

https://360learning.com/

Connect with David Kreiger:

https://www.linkedin.com/in/davidkreiger/

https://salesroads.com/

Subscribe to the podcast and follow our Podcast LinkedIn page so you don't miss any episodes!

https://www.linkedin.com/company/sell-like-a-leader-podcast/