The Future of B2B Marketing with Kieran Flanagan

32 snips

Jan 5, 2026

Kieran Flanagan, SVP of Marketing at HubSpot and former CMO at Zapier, dives into the transformative impact of AI on B2B marketing. He shares his unique 'two-year mission' framework for meaningful work and discusses the balance between management and creative roles within large teams. Kieran offers insights on how AI shifts marketing from mere answers to actionable strategies, urging marketers to specialize in either technical integration or creative storytelling. He also warns of AI fatigue while celebrating its potential to enhance craft and personalization.

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ADVICE

Two-Year Mission Framework

Work in two-year missions to earn your stripes and stay motivated.
Timebox goals so you can see impact and avoid burnout by rotating missions every two years.

ANECDOTE

YouTube Grind Taught Persistence

Kieran describes grinding on YouTube pivot that nearly killed him but taught persistence.
The hard grind separated those who succeeded from those who did not.

ADVICE

Be Clear About How You Work

Write a 'how to work with me' doc and use AI to surface honest feedback about your style.
Use push-and-pull: declare quarters you will be in the weeds and expect others to pull you in when needed.

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#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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