Optimizing for AI Assistants

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

• Why prompting and context engineering are the most important skills for GTM operators
• How “vibe prompting” accelerates learning and output with LLMs
• The three keys to building AI fluency inside teams
• Measuring ROI from AI across sales, marketing, and operations
• Why every professional is now a manager (of AI agents)
• How websites will evolve into multimodal closing mechanisms
• The rise of personality-led growth in B2B marketing
• Why curiosity and persistence matter more than ever in an AI-first world

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.