Kieran Flanagan is the SVP of Marketing at HubSpot and Co-Host of Marketing Against the Grain. A longtime operator and investor, he’s at the forefront of how AI is reshaping go-to-market. With a background in engineering and years leading growth and marketing teams, Kieran now spends his time building, experimenting, and sharing lessons on how prompting, agents, and personality-led growth will define the next era of software companies.
Discussed in this episode
Episode highlights
00:46 — The 100x difference between good and bad prompting
03:57 — The rise of “context engineering” as a GTM skill
07:22 — Kieran’s 3-part framework for AI fluency inside teams
09:31 — Why “vibe prompting” is as powerful as vibe coding
11:00 — How AI boosts conversions & deal velocity in sales workflows
15:10 — Using ChatGPT memory as a personalized prompting coach
22:19 — Everyone now manages a PhD-level AI intern
31:12 — The 3 biggest shifts coming to GTM: influence, AI optimization, multimodal
37:42 — Why AI makes human creativity more valuable than ever
43:06 — The grind, reps, and curiosity as the ultimate AI skills
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Guest links
LinkedIn: https://www.linkedin.com/in/kieranjflanagan/
Newsletter (The AI Marketing Generalist):https://www.kieranflanagan.io/
Podcast (Marketing Against the Grain):https://www.youtube.com/@MATGpod/videos
Host links
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
X (Twitter): https://x.com/sophiebuona
Newsletter: https://thegtmnewsletter.substack.com/
Website: https://gtmnow.com
The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.