Learning through brutal feedback and copy work

#318 | Dave is joined by Kieran Flanagan, SVP of Marketing at HubSpot and former CMO at Zapier. They break down how AI is reshaping B2B marketing workflows, content creation, and team structure, plus Kieran’s leadership philosophy for managing a 300+ person team while staying deeply involved in creative execution. 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 + why AI matters now
• (04:28) - – Kieran’s career + the 2-year mission framework
• (09:58) - – The grind, early-career advice, and earning your stripes
• (12:28) - – Operator vs. manager + strong opinions in leadership
• (20:28) - – Why collaborative brainstorms fail
• (25:28) - – ChatGPT vs. Claude + how Kieran actually uses AI
• (33:16) - – Where AI is taking B2B marketing (answers → actions)
• (44:46) - – Picking a lane: technical vs. creative marketers
• (52:16) - – The future CMO + agencies, in-person, and what still matters

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