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

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May 27, 2025

Sean Whiteley, a three-time founder and CEO of Qualified, shares his insights on navigating tech shifts from the internet to AI. He delves into the accelerated pace of AI adoption and its reshaping of RevOps and team structures. Whiteley discusses the evolving nonlinear buyer journey, the need for success teams at the core of go-to-market strategies, and dispels common GTM myths. He emphasizes the importance of strategic collaboration and the traits he looks for in co-founders, ensuring companies can thrive in a rapidly changing environment.

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INSIGHT

Speed Drives Platform Shifts

Speed is the defining change across tech platform shifts; time to value and market has dramatically shortened.
AI further accelerates this, challenging historic methods in operations, processes, and team structures.

INSIGHT

Ops Teams Are AI Orchestrators

Operations teams gain importance as they control data, systems, and processes critical for AI orchestration.
AI enables automation of many workflows, transforming org structure and workflow execution fundamentally.

INSIGHT

Buyers Control The Process

The buyer now has all the power and controls a nonlinear, AI-assisted buying process.
Vendors must adapt to buyer-led research fueled by AI agents and community insights.

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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The most common GTM myth Sean is seeing today—and why it’s outdated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 GTMnow Podcast
The GTMnow 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.

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