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The Seat
Sean McCaffrey, President & CEO - GSTV
Episode Summary:
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. Sean also shares what surprised him most as a CEO, how board service keeps him sharp, and what he looks for in future leaders; grit, curiosity, and being a perpetual student, especially as AI reshapes every function.
Themes Discussed:
- From athlete to executive: How team sports shape leadership and culture
- Accidental entry into advertising & sales and discovering OOH as a career
- The evolution of out-of-home: From static boards to audience-led digital engagement
- Scaling through consolidation: Navigating growth from regional to global organizations
- Solutions-based selling: Marketing conversations vs. “selling inventory”
- Leading through uncertainty: The Clear Channel go-private saga and lessons learned
- Control vs. Influence mindset: Why it matters even more in the AI era
- Mentorship & leadership modeling: Active listening, passion, and high character
- CEO realities: Decision-making, consensus-building, and moving fast without perfect info
- Developing future leaders: Curiosity outside scope, skill gaps, and continuous learning
Chapters:
00:00 - Intro & Sean's Background
06:52 - First sales role, Universal Outdoor & “accidental” entry into OOH
08:03 - What OOH looked like in the late 90s, regulation, real estate, national vs local
11:16 - Consolidation era, Universal/Eller to Clear Channel & learning the full business
22:01 - Leading through uncertainty - go-private chaos and the “Venn diagram” framework
26:57 - Mentors & values, passion, character, playing the long game
32:17 - Why GSTV & CEO lessons, decision velocity, boards, developing leaders
Keywords:
GSTV, Sean McCaffrey, out-of-home advertising, OOH, DOOH, retail media, convenience retail, video network, Clear Channel Outdoor, leadership, CEO, sales leadership, strategy, partnerships, change management, mentors, decision making, organizational growth, private equity, consolidation, brand safe media, measurement, audience addressability, AI in advertising, executive presence, boards, IAB, Ad Council, OAAA, DPAA, The Seat podcast
Sean's Bio:
Sean McCaffrey is President & CEO of GSTV, the nation’s leading video network at fuel and convenience retailers, reaching over 116 million Americans each month. He previously spent 16+ years at Clear Channel Outdoor, including as EVP of Strategy & Partnerships, leading enterprise revenue strategy and global agency relationships. Sean serves on the boards of the IAB Digital Video Center of Excellence, the Ad Council, OAAA, and DPAA. A former college football player at Drake University, he brings an athlete’s mindset to leadership, culture, and long-term growth.
GSTV's Website:
https://www.gstv.com/
Ray's Bio:
Ray Erickson is the host of The Seat, a podcast featuring 1:1 conversations with revenue leaders across media, marketing, and advertising, unpacking the early days, mentors, setbacks, and pivotal moments that shaped how they lead today. Ray is a longtime ad/media sales leader with experience spanning digital ad tech, CTV, and sports media, and he created The Seat to sharpen his own leadership edge while paying it forward to the next generation of aspiring sales leaders.
Social Links:
Instagram: @theseat.pod
TikTok: @theseat.pod
LinkedIn: The Seat Podcast (LinkedIn Page)
Host: Ray Erickson (LinkedIn)
Listen:
Apple Podcasts / Spotify / iHeart / SiriusXM / Acast
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5. Matt Ryter, VP Video Sales - Minute Media
48:09||Season 2, Ep. 5Episode Summary / Description: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."Themes Discussed:Finding your lane early (and learning what you don’t want to do)Breaking into sales without the “traditional” entry pathMentorship and the power of shared networksLeadership lessons from both great and bad managersPlayer-coach growing pains: teaching vs “I’ll just do it myself”Building a business from zero (Genius Sports)Selling tech & data vs selling media & contentCulture-first career moves and “kismet timing”Managing hybrid/remote teams without micromanagingPersonal brand, networking, and staying sane in the grindChapter Breakdown:00:00 - Intro02:02 - Providence College & early direction04:26 - ESPN stats job: dream…then burnout06:28 - CBS entry: ad ops & inventory grind07:36 - Breaking into sales via CNNMoney11:26 - Mentorship: Providence alum opens doors15:31 - Leadership begins: NFL then Genius17:16 - Genius Sports: build team from zero31:21 - Minute Media: “everything collided”36:14 - Trust-based leadership & hiring lessonsKeywords:Minute Media, Sports Illustrated, The Players’ Tribune, FanSided, SendToNews, Genius Sports, NFL, ESPN, CBS, Time Inc., CNNMoney, digital video, sports media, ad sales, leadership, mentorship, personal brand, networking, remote leadership, CTV, FAST channels, streaming, collaboration, trust, sales management, career growthMatt's Bio:Matt Ryter is the Vice President of Sales at Minute Media, where he leads commercial video sales initiatives and supports the company’s broader monetization strategy across premium sports storytelling and distribution. Previously, Matt served as VP of Sales at Genius Sports, helping build and scale the brand advertising business in North America. He also held roles at the NFL, Time Inc. (including Sports Illustrated / Fortune ecosystem), CBS, and ESPN. Matt is a proud Providence College alum and lives in the New York metro area with his wife and two children.Ray's Bio: Ray Erickson is the host of The Seat, a podcast featuring 1:1 conversations with revenue leaders across media, marketing, and advertising — unpacking the early days, mentors, setbacks, and pivotal moments that shaped how they lead today. Ray is a longtime ad/media sales leader with experience spanning digital ad tech, CTV, and sports media, and he created The Seat to sharpen his own leadership edge while paying it forward to the next generation of aspiring sales leaders.Social Links:Instagram: @theseat.podTikTok: @theseat.podLinkedIn: The Seat Podcast (LinkedIn Page)Host: Ray Erickson (LinkedIn)Listen: Apple Podcasts / Spotify / iHeart / AcastMinute Media Website: https://www.minutemedia.com/
4. Brie Thomas, SVP of Sales - Swoop
39:49||Season 2, Ep. 4Episode Description: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.The conversation explores empathy in leadership, managing through self-doubt, motivating without micromanaging, and how sellers can future-proof their careers in a rapidly changing media landscape. A must-listen for sellers stepping into management and leaders focused on building durable, people-first organizations.Key Themes:Building trust as the foundation of leadershipTransitioning from individual contributor to player-coachLeading without micromanagementManaging self-doubt and imposter syndromeMotivating teams in high-pressure environmentsNavigating regulated industries with integrityWhat aspiring sales leaders often get wrongEmpathy, energy, and accountability in leadershipChapter Breakdown:00:00 - Trust as the foundation of leadership02:00 - First sales role at iHeartMedia03:45 - Creativity, competition, and early selling lessons06:15 - Relationship-driven selling vs product pitching08:40 - Knowing you’re built for sales10:55 - Transitioning into leadership roles14:50 - What changes from IC to manager17:20 - Trust, motivation, and avoiding micromanagement21:00 - Managing self-doubt and imposter syndrome29:35 - Advice for aspiring sales leadersKeywords:sales leadership, revenue leadership, women in sales, media sales, ad tech careers, healthcare advertising, leadership development, trust in leadership, sales management, player coach, career growth, empathy in leadership, sales mentorship, digital media careersGuest Bio:Brie Thomas is the Senior Vice President of Sales at Swoop, where she leads revenue growth and client partnerships in healthcare advertising, one of the most regulated and complex areas of the media ecosystem. With a career spanning over two decades, Brie began in traditional media sales at iHeartMedia before transitioning into digital advertising, startups, and leadership roles. She has progressed from individual contributor to player-coach, VP, and senior executive, earning a reputation for trust-driven leadership, empathy, and building high-performing teams. At Swoop, Brie has played a key role in the company’s evolution into a market leader, helping advertisers reach patients responsibly through privacy-first, data-driven solutions.Host Bio:Ray Erickson is the host and creator of The Seat and a veteran sales and revenue leader with over 20 years of experience across media, ad tech, and streaming.Ray has held senior leadership roles at companies including Samsung Ads, Conversant, Sizmek, and Victory+, where he built and scaled high-performing sales organizations. Through The Seat, Ray sits down with revenue leaders to unpack the journeys, setbacks, and leadership lessons that shape how executives lead today.Social Links:Instagram: @theseat.podTikTok: @theseat.podLinkedIn: The Seat Podcast (LinkedIn Page)Host: Ray Erickson (LinkedIn)Listen: Apple Podcasts / Spotify / iHeart / AcastSwoop Website: https://swoop.com/
3. Jes Santoro, CRO - Cadent
45:04||Season 2, Ep. 3Episode Description: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, spanning Comcast, Vindico (a major inflection point), and multiple roles shaping cross-screen advertising innovation. Today at Cadent, Jes leads revenue across a suite of solutions designed to help brands and agencies navigate fragmentation, consolidation, and the “share shift” reality of modern advertising.This conversation is packed with practical leadership principles, clear direction, celebrating wins, calm under pressure, and empowering teams, along with what Jes looks for when hiring, how he spots curiosity in interviews, and why aspiring leaders should bring solutions (not just problems).Key Themes:Curiosity is the unlock: It shaped Jes’ entire career and remains his #1 hiring signal.Networking & initiative beats luck: Jes’ “30 Rock resume delivery” story is a masterclass in proactive career ownership.Leadership isn’t knowing the most: It’s hiring smart people, empowering them, and keeping the system on the rails.Clear direction & calm is contagious: Put it on paper, hold accountability, celebrate wins, and stay steady through chaos.Modern growth is share-shift: In a capped market, winning means being sharper, more organized, and more differentiated.Chapter Breakdown:00:00 – Science, Curiosity, and Career Direction02:30 – Breaking Into Media Without a Playbook06:30 – Lessons from Media Buying10:30 – Transitioning from Buyer to Seller18:30 – Early Management Mistakes22:30 – Vindico and Taking Career Risk25:45 – Hiring for Curiosity30:30 – Leadership Evolution Over Time34:45 – The CRO Seat at Cadent39:30 – Advice for Aspiring LeadersKeywords:advanced TV, programmatic, omnichannel advertising, identity, ad tech, CTV, digital video, revenue leadership, CRO, sales leadership, go-to-market strategy, leadership development, curiosity, mentorship, NBC Page Program, BBDO, Comcast, Vindico, TubeMogul, Adobe Ad Cloud, CadentGuest Bio:Jes Santoro is the Chief Revenue Officer at Cadent and a 25-year veteran across enterprise software, advanced TV, and integrated media. He has built and led high-performing revenue organizations and go-to-market strategy spanning TV, digital video, programmatic, and identity. Before Cadent, Jes held senior leadership roles at Adobe Ad Cloud, TubeMogul, Vindico, BBDO, and Comcast, helping shape some of the earliest innovations in advanced TV and cross-screen advertising. He also supports emerging companies as a limited partner with C2 Ventures and serves on industry committees and advisory boards.Host Bio: Ray Erickson is the host of The Seat and a longtime media revenue leader across digital, CTV/streaming, and ad tech. He’s built and scaled high-performing sales teams, launched vertical strategies, and partnered with brands and agencies to drive growth through modern video and data-driven advertising. Ray produces The Seat via Axis Advisory, LLC, where he focuses on executive conversations, revenue leadership storytelling, and advisory work across the media ecosystem.Social Links:Instagram: @theseat.podTikTok: @theseat.podLinkedIn: The Seat Podcast (LinkedIn Page)Host: Ray Erickson (LinkedIn)Listen: Apple Podcasts / Spotify / iHeart / AcastCadent: https://www.cadent.com/
2. Doug Weaver, Coach - The Weaver Collective
51:46||Season 2, Ep. 2Summary: 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.We close with Doug’s next chapter: the Weaver Collective...his curated coaching community designed to develop the next generation of sales leaders.Follow The Seat and stay connected for clips and episode drops:Chapter Timeline: 00:00 Teaser Open00:25 Doug’s intro: Wired, Upstream Group, The Drift, Weaver Collective02:03 Print-era lessons: scrappiness, creativity, “village of lost toys” accounts02:38 HotWired and the early web: what really happened in 199405:01 Young Doug: wanting to be a teacher & the mentor who shaped him06:34 What we’ve “lost” (and haven’t): consolidation then vs. now09:01 The Upstream origin story: how training happened by accident14:21 The #1 seller mistake: relationship diversification & proactive demand creation18:01 The #1 leader mistake: solving problems vs. coaching the process40:29 The next chapter: Weaver Collective, community coaching, and what to protect in the professionKeywords:Doug Weaver, Upstream Group, Weaver Collective, digital advertising, media sales, ad tech, CRO, revenue leadership, sales management, sales training, account strategy, consultative selling, demand creation, agency relationships, consolidation, IAB, HotWired, Wired, leadership coaching, mentorship, ethics in advertising, sales processGuest Bio (Doug Weaver):Doug Weaver is one of the architects of modern digital media sales. He spent nearly three decades as Founder & CEO of Upstream Group, advising 900+ media and technology companies including Wired, Spotify, Hulu, Facebook, BuzzFeed, Vevo, and The New York Times. Doug authored The Drift for more than 20 years, helped shape the foundational years of the industry, and trained thousands of sellers and leaders across media and ad tech. Today, he coaches senior leaders through the Weaver Collective at weavercollective.net.Host Bio (Ray Erickson):Ray Erickson is the creator & host of The Seat and a revenue leader across media, ad tech, and streaming. He’s held leadership roles at Samsung Ads, Conversant/Epsilon, and Katz Media, and is the founder of Axis Advisory, LLC. On The Seat, Ray sits down one-on-one with revenue leaders to unpack the early days, mentors, setbacks, and moments that shape how executives lead.Follow Us on Social:Instagram: @theseat.podTikTok: @theseat.podLinkedIn: The Seat Podcast