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 cultureAccidental entry into advertising & sales and discovering OOH as a careerThe evolution of out-of-home: From static boards to audience-led digital engagementScaling through consolidation: Navigating growth from regional to global organizationsSolutions-based selling: Marketing conversations vs. “selling inventory”Leading through uncertainty: The Clear Channel go-private saga and lessons learnedControl vs. Influence mindset: Why it matters even more in the AI eraMentorship & leadership modeling: Active listening, passion, and high characterCEO realities: Decision-making, consensus-building, and moving fast without perfect infoDeveloping 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 Hosted on Acast. See acast.com/privacy for more information.
