Future CMO, agencies, and in-person trends

#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

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive.

AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.

Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. 

***

Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

• They give you unlimited podcast editing and strategy for your B2B podcast.
• Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.
• Visit hatch.fm to learn more