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.