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GTM 148: Winning Every Tech Shift from a 3X Founder (From Internet to AI)

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Manage episode 485279838 series 2465233
Content provided by GTMnow by GTMfund. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by GTMnow by GTMfund or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

Sean Whiteley is a three-time founder and the current CEO of Qualified, the AI pipeline automation platform purpose-built for inbound GTM teams. Previously, he founded GetFeedback (acquired by Campaign Monitor) and Kieden (acquired by Salesforce), where he also served as SVP & GM. With over two decades at the forefront of tech’s biggest transformations—from on-prem to cloud to AI—Sean offers a rare, long-term view on how to build companies and go-to-market engines in the face of massive disruption.

Discussed in this Episode:

  • Why the speed of AI adoption outpaces every previous tech wave
  • How the role of RevOps and team design is being reshaped by agentic systems
  • Why today’s buyer journey is nonlinear, AI-assisted, and fully in control
  • Tactical breakdown: how Sean mapped and tagged every task at Qualified for AI automation
  • Why success teams must sit at the core of GTM strategy, not as an afterthought
  • The most common GTM myth Sean is seeing today—and why it’s outdated
  • The characteristics Sean looks for in long-term co-founders and GTM hires

Highlights:

02:00 Sean’s journey through on-prem, cloud, and now AI
05:00 Ops leaders as the new AI orchestrators inside GTM teams
08:30 From workflows to autonomous agents: how org charts are shifting
10:30 The “two-way doors” mindset for fast experimentation
13:30 The future of GTM: agents, trust falls, and buyer-led journeys
15:00 From personalization to “relevance at scale” in modern marketing
18:00 AI unlocks speed and efficiency—how that reshapes CAC payback and TCO
24:00 How Qualified created internal AI blueprints across every team
28:30 Inside the AI SDR: replacing manual inbound sales with 24/7 automation
32:00 Success is not post-sales—it’s the center of the GTM experience
36:00 Reinventing yourself as a founder through three companies
39:30 What still hasn’t changed: customer value and trusted partnerships
47:00 GTM myth: “We control the buying process”—why that’s dead
51:00 Where Sean learns about AI: customer conversations > thought leadership

Guest Speaker Links (Sean Whitely):

Host Speaker Links (Sophie Buonassisi):

Where to find GTMnow (GTMfund’s media brand):

The GTM Podcast
The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.

  continue reading

712 episodes

Artwork
iconShare
 
Manage episode 485279838 series 2465233
Content provided by GTMnow by GTMfund. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by GTMnow by GTMfund or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

Sean Whiteley is a three-time founder and the current CEO of Qualified, the AI pipeline automation platform purpose-built for inbound GTM teams. Previously, he founded GetFeedback (acquired by Campaign Monitor) and Kieden (acquired by Salesforce), where he also served as SVP & GM. With over two decades at the forefront of tech’s biggest transformations—from on-prem to cloud to AI—Sean offers a rare, long-term view on how to build companies and go-to-market engines in the face of massive disruption.

Discussed in this Episode:

  • Why the speed of AI adoption outpaces every previous tech wave
  • How the role of RevOps and team design is being reshaped by agentic systems
  • Why today’s buyer journey is nonlinear, AI-assisted, and fully in control
  • Tactical breakdown: how Sean mapped and tagged every task at Qualified for AI automation
  • Why success teams must sit at the core of GTM strategy, not as an afterthought
  • The most common GTM myth Sean is seeing today—and why it’s outdated
  • The characteristics Sean looks for in long-term co-founders and GTM hires

Highlights:

02:00 Sean’s journey through on-prem, cloud, and now AI
05:00 Ops leaders as the new AI orchestrators inside GTM teams
08:30 From workflows to autonomous agents: how org charts are shifting
10:30 The “two-way doors” mindset for fast experimentation
13:30 The future of GTM: agents, trust falls, and buyer-led journeys
15:00 From personalization to “relevance at scale” in modern marketing
18:00 AI unlocks speed and efficiency—how that reshapes CAC payback and TCO
24:00 How Qualified created internal AI blueprints across every team
28:30 Inside the AI SDR: replacing manual inbound sales with 24/7 automation
32:00 Success is not post-sales—it’s the center of the GTM experience
36:00 Reinventing yourself as a founder through three companies
39:30 What still hasn’t changed: customer value and trusted partnerships
47:00 GTM myth: “We control the buying process”—why that’s dead
51:00 Where Sean learns about AI: customer conversations > thought leadership

Guest Speaker Links (Sean Whitely):

Host Speaker Links (Sophie Buonassisi):

Where to find GTMnow (GTMfund’s media brand):

The GTM Podcast
The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.

  continue reading

712 episodes

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