Take a Seat

Ethan Heftman, Chief Revenue Officer at New Tradition, joins Ray Erickson on The Seat to walk through a career built in some of the most competitive and creative corners of media. From his early days in sales to leading revenue at one of the most innovative out-of-home companies in the country, Ethan shares how he got to the CRO seat, what it takes to sell a new medium, and why relationships and reputation are the only currency that really compounds over time.

Kym Insana, Founder & President of AlwaysOn Digital, joins Ray Erickson on The Seat to trace a career built on bold bets, hard pivots, and the kind of leadership that only comes from betting on yourself. From her early days in media to building and running her own company, Kym shares what it really takes to step out on your own, how she thinks about talent, culture, and growth, and why the most important career decisions she made were the ones that scared her most.

Sean Galligan, Chief Revenue Officer at Kochava, joins Ray Erickson on The Seat to break down a career built at the intersection of media, data, and performance marketing. From early days in broadcast and digital to leading revenue at one of the most important measurement and attribution platforms in mobile advertising, Sean shares how he got to the CRO seat, what it takes to lead in a technical sales environment, and why he believes the best leaders are the ones who know how to get out of the way.

In this episode of The Seat, Ray Erickson sits down with Brian Danzis, Global Chief Revenue Officer at Seedtag, to unpack a 25-year journey defined by building, risk-taking, and evolving leadership. From early days at Turner and being one of the first sellers in emerging categories like in-game advertising and streaming video, to scaling global revenue organizations at Spotify and now Seedtag, Brian shares what it really takes to lead.

In this episode of The Seat, Ray Erickson sits down 1:1 with Lindsey Kintner, Global Head of Sales at Foursquare. With more than 20 years across AOL, MySpace, The Wall Street Journal, Condé Nast, Fortune, and now Foursquare, Lindsey shares the key moments that shaped her path from account management into leading global revenue teams. The conversation dives into the importance of storytelling in a data-driven world, what great sales leadership looks like today, and how to identify and develop top talent. Lindsey also shares her leadership mindset, from 'Be the Bison' and facing challenges head-on, to the importance of zooming out to prioritize and act.

In this episode of The Seat, Ray Erickson sits down with Chad Hickey, Founder and CEO of Givsly, for an unfiltered conversation about the career moments, mindset shifts, and late-night decisions that led him to build one of the most innovative companies in advertising today. He opens up about imposter syndrome at the executive level, what turning 40 unlocked in him, and how a volunteer dinner with the CMO of McDonald's China sparked the idea that became Givsly. Chad also shares his will-versus-skill hiring philosophy, what great sales leaders are getting wrong in today's environment, and why the rise of AI is the single biggest opportunity for hungry young professionals to prove their value.

Sara Badler, Chief Advertising Officer, North America, at The Guardian, joins The Seat to discuss her journey from early programmatic pioneer to C-suite leader at one of the world's most respected news organizations. From building global teams at The New York Times and Dotdash Meredith to learning tough lessons at Morning Brew, Sara shares why outcomes matter more than titles and how patience, scrappiness, and ego-free leadership define modern executives.

Sean McCaffrey, President & CEO of GSTV, joins Ray Erickson on The Seat to unpack a 25+ year career spent building at the intersection of media, marketing, and out-of-home. Starting as a young seller in the late 90s, Sean rode the wave of consolidation that shaped modern OOH, grew through 16+ years at Clear Channel, and eventually stepped into the CEO seat at GSTV to build a national video platform at fuel and convenience retail. The conversation spans Sean's athlete mindset from his Drake football days, how early mentors shaped his leadership style, and why 'focusing on what you can control and influence' became a defining principle during a high-stakes period of corporate uncertainty.

In this episode of The Seat, Ray Erickson sits down with Gabrielle Heyman, VP of Global Brand Sales & Partnerships at Zynga, to unpack a 20+ year career built at the intersection of gaming, media, entertainment, and advertising. Gabrielle shares her origin story from early days at CBS.com, the dot-com era and in-game advertising at EA, breakout years at Yahoo, the leap to BuzzFeed, and ultimately her long-term rise at Zynga. They dig into what changes when you go from elite individual contributor to leader; response time, delegation vs. micromanagement, managing up to the C-suite, protecting your time from meetings, and how she thinks about the modern consumer as a 'layman anthropologist.' Gabrielle also breaks down Zynga's business, why mobile is the biggest gaming segment, and how her team monetizes the 95% of players who don't pay through in-app advertising.

Matt Ryter's path to Vice President wasn't linear and that's the point. From a first job logging stats at ESPN (that actually made watching sports worse) to learning the ad business at CBS and Time Inc., Matt's career is a story of finding the right lane, building a personal brand, and growing into leadership by being willing to learn in public. Now VP of Sales at Minute Media, Matt shares how he went from big-company structure to startup chaos at Genius Sports, what he learned building a team from scratch, and why modern leadership is less about control and more about trust, especially in a post-COVID world. Along the way, he breaks down what he looks for when hiring, a common mistake young sellers make ('saying yes' too quickly), and the mantra he lives by, 'Collaboration moves at the speed of trust.'

In this episode of The Seat, host Ray Erickson sits down with Brie Thomas, Senior Vice President of Sales at Swoop, for a candid conversation about trust, leadership evolution, and building high-performing teams in complex environments. Brie traces her career from selling radio spots at iHeartMedia to navigating digital startups, becoming a player-coach, and ultimately leading revenue teams in one of the most regulated sectors in advertising, healthcare. Along the way, she shares how her leadership style evolved, why trust is the foundation of effective teams, and what aspiring sales leaders often misunderstand about long-term success.

In this episode of The Seat, Ray Erickson sits down with Jes Santoro, Chief Revenue Officer at Cadent, to unpack a 25-year journey across enterprise software, advanced TV, and integrated media, built on one consistent trait...curiosity. Jes starts with an unconventional origin story, studying biology and cardiopulmonary physiology, working as a teaching assistant, and nearly heading to medical school, before taking a 'gap year' that changed everything. That pivot led him to New York, a bold hustle into 30 Rock, and ultimately the NBC Page Program, where a single relationship opened doors to an early career at the center of Must-See TV. From there, Jes moves into the agency world at BBDO, where his curiosity about the early internet sparked a leap into entrepreneurship and eventually, a path into sales leadership.

Doug Weaver is one of the true architects of modern digital media sales. He sold web sponsorships in the earliest days of HotWired, helped shape the industry's foundational years, and spent nearly three decades as Founder & CEO of Upstream Group advising 900+ media and technology companies (from Wired and Hulu to Spotify, Facebook, BuzzFeed, and The New York Times) while training thousands of sellers and leaders (including Ray). In this episode, Doug breaks down what's actually changed (and what hasn't) in a world of consolidation, why most sellers plateau when they start making real money, and the most common mistakes he's seen over decades, both for reps and managers. We go deep on relationship diversification, selling 'left of budget,' coaching the process (not solving the problem), and why values and ethics matter more than ever as the stack evolves.

Heather Carver's career is a masterclass in adaptability, leadership, and long-term relationship building. In Season 2, Episode 1 of The Seat, Heather, who JUST stepped into her new role as Chief Customer Officer at tvScientific, joins Ray Erickson to unpack her journey from early ad operations roles to her first CRO seat and beyond. They discuss imposter syndrome, radical candor, emotional intelligence, managing through change, and why strong leadership starts with listening first. Heather also shares how to think about career pacing, mentorship, and what high-performing ICs should do before asking for a leadership role. This conversation is packed with practical lessons for anyone navigating growth in media, ad tech, or leadership.