Episode 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 leadership
• Transitioning from individual contributor to player-coach
• Leading without micromanagement
• Managing self-doubt and imposter syndrome
• Motivating teams in high-pressure environments
• Navigating regulated industries with integrity
• What aspiring sales leaders often get wrong
• Empathy, energy, and accountability in leadership

Chapter Breakdown:

00:00 - Trust as the foundation of leadership

02:00 - First sales role at iHeartMedia

03:45 - Creativity, competition, and early selling lessons

06:15 - Relationship-driven selling vs product pitching

08:40 - Knowing you’re built for sales

10:55 - Transitioning into leadership roles

14:50 - What changes from IC to manager

17:20 - Trust, motivation, and avoiding micromanagement

21:00 - Managing self-doubt and imposter syndrome

29:35 - Advice for aspiring sales leaders

Keywords:

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 careers

Guest 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.pod

TikTok: @theseat.pod

LinkedIn: The Seat Podcast (LinkedIn Page)

Host: Ray Erickson (LinkedIn)

Listen: Apple Podcasts / Spotify / iHeart / Acast

Swoop Website:

https://swoop.com/

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Episode 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 Direction

02:30 – Breaking Into Media Without a Playbook

06:30 – Lessons from Media Buying

10:30 – Transitioning from Buyer to Seller

18:30 – Early Management Mistakes

22:30 – Vindico and Taking Career Risk

25:45 – Hiring for Curiosity

30:30 – Leadership Evolution Over Time

34:45 – The CRO Seat at Cadent

39:30 – Advice for Aspiring Leaders

Keywords:

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, Cadent

Guest 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.pod

TikTok: @theseat.pod

LinkedIn: The Seat Podcast (LinkedIn Page)

Host: Ray Erickson (LinkedIn)

Listen: Apple Podcasts / Spotify / iHeart / Acast

Cadent: https://www.cadent.com/

Hosted on Acast. See acast.com/privacy for more information.

Summary:

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:

1. 00:00 Teaser Open
2. 00:25 Doug’s intro: Wired, Upstream Group, The Drift, Weaver Collective
3. 02:03 Print-era lessons: scrappiness, creativity, “village of lost toys” accounts
4. 02:38 HotWired and the early web: what really happened in 1994
5. 05:01 Young Doug: wanting to be a teacher & the mentor who shaped him
6. 06:34 What we’ve “lost” (and haven’t): consolidation then vs. now
7. 09:01 The Upstream origin story: how training happened by accident
8. 14:21 The #1 seller mistake: relationship diversification & proactive demand creation
9. 18:01 The #1 leader mistake: solving problems vs. coaching the process
10. 40:29 The next chapter: Weaver Collective, community coaching, and what to protect in the profession

Keywords:

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 process

Guest 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.pod

TikTok: @theseat.pod

LinkedIn: The Seat Podcast

Hosted on Acast. See acast.com/privacy for more information.

Description:

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.

Chapter Breakdown:

00:27 - Welcome to The Seat & Heather’s journey (tvScientific / Freestar / Magnite / Amazon)

01:29 - Union College, early ambition, and the “law school” detour

03:49 - Startup life at BusRadio: ambiguity, pivots, and learning fast

04:49 - Snagajob: culture, KPIs, and the “human element” at work

06:49 - Programmatic’s early days: EQ training & “Ad Ops is Sexy” era

10:06 - Match/IAC & NYC network effects: relationships compound

14:01 - IC to Leader: delegation, trust, and imposter syndrome

20:01 - Hard feedback with empathy & Freestar CRO lessons (talent, attitude, systems)

36:42 - Mentorship & visibility: “do the job before the job” + lightning round

Keywords:

career journey, leadership development, ad tech, programmatic advertising, connected tv, women in leadership, mentorship, radical candor, emotional intelligence, sales leadership, customer success, executive growth

Heather's Bio:

Heather Carver is Chief Customer Officer at tvScientific, where she leads customer and partner strategy focused on measurable outcomes in connected TV and programmatic advertising. Previously, Heather served as the first Chief Revenue Officer at Freestar and held senior leadership roles at Magnite, Amazon Ads, and other leading ad tech companies. With over 15 years of experience across SSP's and DSP's, Heather is known for her customer-first approach, operational expertise, and people-centric leadership style.

She also serves on the board of the Women in Programmatic Network and actively advises emerging ad tech companies

Ray's Bio:

Ray Erickson is the creator and host of The Seat, a podcast featuring one-on-one conversations with senior revenue and business leaders across media, marketing, and advertising. A longtime ad tech and CTV media executive, Ray focuses on unpacking the real career journeys behind leadership titles, the mentors, missteps, and moments that shape how executives lead today.

Social:

Instagram: @theseat.pod

TikTok: @theseat.pod

LinkedIn: The Seat Podcast

Hosted on Acast. See acast.com/privacy for more information.

Description:

Matt Weisbecker is a media and advertising executive with 30 years of experience building and scaling revenue organizations across broadcast, digital media, and ad tech.

In this episode, Ray Erickson sits down with Matt to trace the full arc, from an unexpected start at AOL (selling early digital programs like search banners and helping shape revenue models for iconic brands like AIM), to leading in complex organizations like NBC, to building high-performing teams across roles at Amazon, GumGum, Epsilon/Conversant, and as Chief Revenue Officer at MyCode.

Matt shares what great leadership actually looks like day-to-day...adapting your leadership style to different personalities, staying transparent with teams (“go do this… and here’s why”), and why “professional persistence” is one of the most underrated skills in sales.

They also dig into a practical edge for modern sellers...storytelling that works in today’s shorter meetings, and why listening, including being comfortable with silence, often gets you the truth faster than talking.

Chapter Breakdown:

01:45 - Morning routine: gratitude, mushroom coffee, news scan

04:56 - Falling in love with digital & building inside sales at AOL

06:35 - When leadership became the path (and why)

11:47 - Mentorship theme: who shaped Matt’s leadership

12:01 - AOL mentor story, Paul Corvino & the Motorola meeting

15:27 - NBC mentors & the “empower your people” leadership model

24:49 - Advising founders now: what leaders consistently underestimate

29:08 - What he hopes people say about working for him (impact, trust, “I have your back”)

33:27 - Sales skills that matter, professional persistence, storytelling, transparency

38:24 - Listening, reading the room, and being comfortable with silence

41:42 - Lightning round

43:18 - Ray’s recap & closing thoughts

44:15 - Outro / where to follow The Seat

Keywords:

sales leadership, mentorship, professional persistence, digital advertising, ad tech, media sales, leadership development, storytelling in sales, listening skills, transparency in leadership, managing up, managing down, AOL, NBC, Amazon Ads, GumGum, Epsilon, Conversant, MyCode, multicultural marketing, Mundial Media, ThinkLA

Matt's Bio:

Matt Weisbecker is a media and advertising executive with 20+ years of experience building and scaling revenue organizations across broadcast, digital media, and ad tech. He’s held leadership roles at AOL, NBC, Amazon, GumGum, and Epsilon/Conversant, and most recently served as Chief Revenue Officer at MyCode. Today, Matt is an Executive Advisor at Mundial Media, partnering with leadership teams on growth and commercial strategy, and serves on the board of ThinkLA.

Ray's Bio:

Ray Erickson is a media and advertising sales leader with deep experience in CTV, digital, and ad tech. On The Seat, he interviews revenue executives to unpack the mentors, setbacks, and defining moments that shape how sales executives lead.

Follow The Seat:

• LinkedIn: The Seat Podcast
• Instagram: @theseat.pod
• TikTok: @theseat.pod
• Subscribe: Apple Podcasts | Spotify | iHeart

Hosted on Acast. See acast.com/privacy for more information.

In this episode of The Seat, host Ray Erickson sits down with Jeff Pabst, a seasoned media and technology revenue leader who has built and scaled teams across radio, ad tech, music streaming, gaming, and the creator economy. Jeff shares how curiosity shaped his career moves, why mentorship and coaching are force multipliers, and how to build repeatable systems that drive revenue growth.

From his early days selling radio at Interep to leadership roles at ShareThis, Shazam, and FaZe Clan, Jeff breaks down the mindset and operating principles he uses to hire, develop, and scale high-performing teams, plus the simple question a CTO asked him that still guides how he thinks about success: are you a builder or a seller?

In this episode, we cover:

• The “builder vs. seller” framework and why sales matters to company health
• Why curiosity is the trait Jeff hires for (and can’t teach)
• How to build a repeatable system for scaling revenue teams
• Mentorship, coaching, and creating a feedback loop that actually works
• The “learning years vs. earning years” idea and career pacing for future leaders
• Why investing in your network is even more important in a remote-first world

00:00 - Cold Open: Builder or seller?

00:41 - Intro: Jeff Pabst and what we’ll unpack

01:48 - LA / morning routine / getting started

03:04 - The early days: Radio sales, training, and mentorship

05:17 - Negotiation + the pull toward digital

06:20 - UC Davis, “nepo baby” origin, and first break into media

08:58 - Quarter-life crisis + traveling the world

09:27 - Specific Media: early digital + cold-calling muscle

12:02 - ShareThis: first-time manager, scaling fast, building systems

16:40 - Scaling revenue orgs: spotting trends before they happen

18:04 - Leadership: hiring mistakes, diverse teams, toolkits, training

22:13 - Hiring filter: curiosity, coachability, competence, execution

26:03 - Failure → opportunity: the interview that changed everything

27:48 - Mentors, peers, coaching, and managing pressure

30:20 - Advice that stuck: builder vs. seller + the power of phone calls

34:40 - Mentorship story: building alongside a key leader

37:01 - The through line: interest + people + culture

39:25 - Creator economy + where media is headed

41:07 - Advice to future leaders: learning years vs. earning years

44:44 - Speed round: Surfline, Chicago, and Pivot

46:28 - Wrap

Keywords

career journey, media advertising, digital media, leadership, high-performing teams, mentorship, sales growth, communication, networking, sales advice, creator economy, ad tech, programmatic, go-to-market, revenue leadership, sales management, coaching, building systems, radio to digital, Shazam, ShareThis, FaZe Clan

Guest bio (Jeff Pabst)

Jeff Pabst is a seasoned media and technology revenue leader with 20+ years of experience building and scaling high-performing commercial teams across ad tech, music streaming, gaming, and the creator economy. He has held senior roles at Interrep, Specific Media, ShareThis, Shazam, Loaded, and FaZe Clan, and is known for his people-first leadership style, curiosity, and ability to create repeatable systems that scale revenue. Jeff currently provides executive strategy at FaZe Clan and is Managing Partner at Second Point Advisors, where he advises founders and growth-stage companies on go-to-market and commercial strategy.

Host bio (Ray Erickson)

Ray Erickson is the host of The Seat and a sales leader in media, marketing, and advertising with deep experience across CTV, programmatic, streaming, and digital video. Ray has built and led revenue teams across the ad ecosystem and is passionate about unpacking the real stories behind revenue leadership, the mentors, setbacks, and defining moments that shape how executives lead.

Follow The Seat:

• LinkedIn: The Seat Podcast
• Instagram: @theseat.pod
• TikTok: @theseat.pod
• Subscribe: Apple Podcasts | Spotify | iHeart

Connect with Jeff:

• LinkedIn: https://www.linkedin.com/in/jeffrey-pabst/
• Company/Advisory: https://www.linkedin.com/company/second-point-advisors/

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In this episode of The Seat, host Ray Erickson sits down with Michael Rosen, Chief Revenue Officer at Origin Media, for an honest conversation about leadership, mentorship, and what it really takes to build and scale high-performing teams.

Michael shares his journey across media, marketing, and sales leadership roles, from early career lessons to executive leadership, highlighting the mentors who shaped his path, the importance of empathy, and the balance between accountability and care. He unpacks how trust, vulnerability, and perspective-driven leadership create stronger organizations and better outcomes.

Whether you’re an aspiring sales leader or a seasoned executive, this conversation offers practical insights on leading through change, empowering teams, and growing as a leader while staying grounded.

Key Themes & Topics Discussed

• The role of mentorship in long-term career growth
• Leading with empathy without sacrificing accountability
• Building trust and psychological safety within teams
• Navigating organizational change and uncertainty
• Developing leaders by encouraging initiative and perspective
• Why vulnerability and honesty strengthen leadership credibility
• Lessons learned from scaling teams across media and tech

Key Takeaways

• Mentorship plays a critical role at every stage of a career
• Empathy is a leadership strength, not a weakness
• Trust and open communication drive better team performance
• Continuous learning is essential for long-term growth
• Great leaders empower others rather than control outcomes

Notable Quotes

• “I think mentorship comes in three flavors.”
• “I want you to come with a perspective.”
• “Leadership is about caring deeply and being honest.”

Episode Chapters

00:00 - Early education and career aspirations

03:27 - Mentorship and early career lessons

06:35 - Transitioning into leadership roles

12:31 - Navigating change management

17:22 - Rebranding and revenue challenges

19:47 - Building and leading strong teams

25:40 - The evolving role of mentorship

32:06 - Empathy, vulnerability, and leadership

39:29 - Michael’s current role at Origin Media

40:02 - Closing thoughts

About the Guest:

Michael Rosen is the Chief Revenue Officer at Origin Media, a connected TV creative ad platform. He brings over 25 years of experience building and scaling media businesses across companies including Intersection, Foursquare, First Look Media, AT&T, WeatherBug, and Bloomberg. Michael also serves on the boards of The New York Pops and Sandy Hook Promise and is co-chair of the UJA-Federation of New York Marketing Council.

Keywords / Tags

leadership, mentorship, sales leadership, media executives, career development, empathy, team building, change management, professional growth, ad tech, marketing leadership, CRO

Follow & Connect

🎙️ Host: Ray Erickson

📸 Instagram: @theseat.pod

🔗 LinkedIn: The Seat Podcast

🎵 TikTok: @theseat.pod

🌐 Listen & stream: https://shows.acast.com/the-seat

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In this episode of The Seat, Ray Erickson sits down with Ryan Spicer, Chief Revenue Officer at Atmosphere TV, to unpack how a former teacher and soccer coach broke into media, took smart risks, and built a leadership style grounded in self-awareness and accountability.

Ryan shares how he literally begged for his first media job at VH1, why he made a controversial lateral move from digital back to linear TV at Turner, and how that decision later put him in the perfect position to lead integrated sales teams.

They dive into the shift from individual contributor to manager, what a CRO actually does at a high-growth company, and why every rising seller needs both mentors and advocates in their corner. If you’re a 30-something seller eyeing the CRO seat one day, this one’s a blueprint.

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