#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
(02:34) - – Kieran’s marketing journey
(04:34) - – His 2-year mission framework
(06:34) - – Advice for early-career marketers
(08:04) - – Why the grind still matters
(09:34) - – Ireland’s SaaS and startup scene
(10:34) - – Balancing operator vs. manager
(12:34) - – AI-generated “How to work with me”
(15:04) - – Kieran’s push-and-pull leadership style
(16:34) - – Giving direct creative feedback
(18:34) - – Why “collaborative brainstorms” fail
(19:34) - – The value of strong opinions
(20:34) - – Learning through tough feedback
(21:34) - – ChatGPT as a creative partner
(23:34) - – Claude vs. ChatGPT vs. Gemini
(25:34) - – Prompting differences in GPT-3.5 vs. 4.0
(29:50) - – Decision fatigue and AI loyalty
(30:50) - – Where AI is taking B2B marketing
(31:50) - – From answers to actions
(33:50) - – Micro-audiences and personalization
(35:50) - – The return of branded traffic
(36:50) - – Why AI reignited Kieran’s spark
(38:50) - – Avoiding AI-induced multitasking burnout
(40:20) - – Deep work vs. whack-a-mole
(41:20) - – Don Draper meets ChatGPT
(42:20) - – Picking a lane: tech vs. creative
(43:50) - – The value of podcasting practice
(44:50) - – Building a prompt muscle
(46:50) - – How Kieran trains GPTs
(48:50) - – Prompting tips for marketers
(49:50) - – The future CMO: part IC, part leader
(50:50) - – How agencies will evolve with AI
(51:50) - – In-person is back
(52:50) - – Overrated AI use cases
(53:50) - – Favorite tool: GenSpark
(55:50) - – Mistakes marketers make with AI
(56:50) - – Does anyone care if it’s AI?
(57:50) - – Lessons from fatherhood
(58:50) - – Final thoughts and wrap-up

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