MySalesDay

In this episode of the My Sales Day podcast, Michael Hess sits down with Doug Weaver to explore what happens when a long, successful chapter ends—and what the next one requires of modern sales leaders.

Doug reflects on the emotional reality of moving on from Upstream Group after a multi-decade run, why creating a “proper ending” mattered, and what it feels like to step into a new venture as a solo act. From there, the conversati...

What separates good sellers from great ones usually isn’t hustle—it’s self-awareness.

In this episode of the My Sales Day podcast, host Michael Hess sits down with Ryan Picchini (CRO at dotCMS) to unpack a skill most sellers avoid: analyzing your own selling behaviors. Ryan explains why self-evaluation is the lever that improves win rates, strengthens relationships, and helps sellers build a repeatable path to performance—not ju...

Prospecting hasn’t gotten easier—but it has gotten more human.

In this episode of the My Sales Day podcast, Michael Hess welcomes back Susan Unger, a career prospector who quite literally does this work for a living. Susan is a senior “door opener” at Kopp Consulting, where her sole focus is securing first meetings with C-level decision makers when no prior relationship exists. If anyone understands the emotional grind of cold o...

In today’s selling environment, you get fewer shots with buyers—and less time when you get them. That’s why meeting management (or better: conversation management) has become a modern sales superpower.

In this episode of the MySalesDay podcast, Michael Hess sits down with Lawrence Horne—joining from the UK countryside—to break down what great sellers do before, during, and after a buyer conversation to earn trust, control moment...

AI has moved past the “is this real?” phase—and entered the “who’s actually adopting it well?” phase. In this episode of the My Sales Day podcast, Michael Hess sits down with Jason Tsai (joining from London) to break down what AI is actually doing inside modern sales orgs, where teams are still stuck, and how B2B sellers can use AI to sell more—not just produce more “work.”

Jason shares the career path that led him from media pl...

In this episode, Grant le Riche, VP of Client Strategy at Eighty Twenty joins me to dive into the mindset required to master the complex sales process. Grant shares how his career evolved from highly transactional sales to a more strategic, consultative approach. We talk about the importance of preparing for every interaction, even when you think it's just a formality, and how he recovered a deal after his boss "junked up" a meetin...

Qualifying clients is the invisible sword every seller must wield, but too few do so effectively. Penry Price, Founding and Managing Partner at Charcoal Advisors, joins me to explore why qualifying is foundational to successful selling, despite often being underutilized. Penry leans on his experiences at Google, LinkedIn, and other major media entities to highlight how a disciplined approach to qualifying protects precious selling ...

Charlie Thomas, Founder of Charlie Thomas Coaching & Consulting, doesn’t focus on pitching harder. Instead, he leans on point of view selling to think bigger. Charlie joins me to share how bold ideas and strategic alignment can transform not just deals, but careers. He recounts the day he closed a multimillion-dollar partnership with Dr. Pepper Snapple by inventing a value-driven offsite on the fly, and how that single act help...

Recruiting isn’t just about filling positions but changing lives. Mike Giunta, Managing Director at TalentClimb, joins me to talk about the deeper human side of recruiting, sharing stories of how his careful, ethical approach has built lasting trust and stronger client relationships. From his decision to lose a lucrative placement because of a recruit’s falsified credentials to understanding candidate motivations beyond just career...

To Daryl Faulkner, Account Director at Heritage Werks, “patient tenacity” isn’t just a phrase — it’s a proven strategy. In this episode, Daryl breaks down how he closed a surprising incremental deal with a legacy client known for not having budget. He also shares how attentive listening, long-term relationship building, and asking the right questions set him up to capitalize when a new budget opportunity appeared. We also discuss w...

Human-centered selling requires more than just closing deals — it means understanding people, showing empathy, and leading with purpose.

In this episode, Doug Weaver, Founder and CEO at Upstream Group, joins me to share the timeless lessons he’s learned from decades of teaching and practicing sales. From a creative career-defining win at Allure Magazine to decades of training top sellers in digital media, connected TV, online au...

Sales career growth takes more than just hitting quota. In this episode, Joe Didato — a sales veteran with over 25 years of experience in media, ad tech, and SaaS — breaks down what it really takes to advance and stay relevant. From relationship-driven selling to winning big accounts through custom value alignment, Joe shares practical wisdom that’s helped him thrive across industries. He also reflects on lessons learned the hard w...

Strategic sales relationships take time — and Erin Frey knows the payoff. As Senior Account Executive at Nexxen, Erin shares how she transitioned from the buy side to becoming a trusted, long-term partner to clients. 

In this episode, Erin dives into the power of empathy and relationship-building in a fast-moving and unpredictable sales world. We discuss how to balance transactional and strategic selling, why courage matters mor...

Sales is more than just closing deals — it’s about discipline, evolution, and knowing when to adapt.

Nik Kontoulas, Managing Director ANZ at Seedtag and CEO and Founder of JustEggs, joins me to share his journey from an ambitious young seller to launching and selling a business — twice. Nik unpacks the evolution of the sales pitch, explaining why the best sellers are those who anticipate market changes before anyone else. He also d...

What are the ingredients to a great sales pitch?

According to Matt Rosenberg, Principal Consultant at First Chair Marketing, they’re storytelling, collaboration, knowing how to find and use sales enablement help.

Matt shares insights with me from his experience leading sales solutions teams and working hand-in-hand with sellers as well as consulting for businesses with widely different sales cultures.

He discusses why tea...

Big sales typically don’t happen overnight — momentum builds in increments.

Stuart Prentice, Senior Account Executive at Nexxen, joins me to break down how resilience in sales isn’t about grinding endlessly but about recognizing and capitalizing on small wins. We discuss the power of incremental selling and keeping deals alive through consistent engagement, adding value before contracts are signed, and strategically re-igniting ...

In this compelling episode, Steve Loguidice, CEO and founder of Varisa Strategic Advisers, shares hard-earned lessons from his 22 years in the industry.

Steve talks about how he turned a long-shot pitch into a groundbreaking deal with MTV during his time at BuzzFeed. By focusing on the client’s needs and aligning with their long-term goals, Steve was able to create a campaign so effective it became the blueprint for future ...

Stephen Clifford (Cliff), Managing Director of East Coast Client Partnerships at Infillion, thinks a lot of sales professionals spend too much time behind a screen — and not enough of it getting in front of their clients.

Cliff shares how creative outreach (like a game of pickleball) and empathy-driven approaches can help sellers connect with even the toughest decision-makers. He also discusses the importance of asking tough que...

Resilience defines every great salesperson, and Nena Slifer, Vice President of Healthcare Strategic Partnerships at iHeartMedia, has embodied it in every step of her career.

From overcoming the challenges of being a young, single mother to mastering enterprise-level sales, Nena’s journey is a testament to grit, thoughtfulness, and strategic vision. She shares how she turned a rejected pitch into a multi-season podcast, the delic...