#257 AI Strategy | Dave is joined by Kieran Flanagan, SVP of Marketing at HubSpot and former CMO at Zapier. Kieran is a rare blend of technical operator, creative strategist, and team builder. He’s spent his career pushing the edges of B2B marketing, most recently through his work leading AI transformation initiatives at scale.

Dave and Kieran cover:

• How AI is reshaping B2B marketing workflows, content creation, and team structure
• Why the best marketers will specialize at the “outer edges” of creativity or technical execution (and what happens if you stay stuck in the middle)
• Kieran’s leadership philosophy: how he manages 300+ people while staying deeply involved in creative execution

Whether you’re leading a marketing team or sharpening your own skills, this episode offers a clear look at how AI is changing the game and how B2B marketers can stay creative, strategic, and indispensable in the process.

Timestamps

• (00:00) - – Intro

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