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

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• The most common GTM myth Sean is seeing today—and why it’s outdated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):

• LinkedIn: https://www.linkedin.com/in/seanwhiteley
• Qualified Website: https://www.qualified.com

Host Speaker Links (Sophie Buonassisi):

• LinkedIn: https://www.linkedin.com/in/sophiebuonassisi
• Newsletter: https://substack.com/@sophiebuonassisi

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

• Website: https://gtmnow.com
• LinkedIn: https://www.linkedin.com/company/gtmnow
• Twitter/X:

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.