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/

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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.

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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.

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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

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