Sean Whiteley is a three-time founder and the Co-Founder 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The most common GTM myth Sean is seeing today—and why it’s outdated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: https://x.com/GTMnow_
YouTube: @gtm_now
The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/

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.

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

The GTMnow Podcast