GTM 165: Vibe prompting, AI fluency, and the new rules of go-to-market | Kieran Flanagan

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Sep 30, 2025

Kieran Flanagan, SVP of Marketing at HubSpot and co-host of Marketing Against the Grain, dives deep into the transformative impact of AI on go-to-market strategies. He discusses the importance of prompting and context engineering, revealing how 'vibe prompting' can enhance learning with LLMs. Kieran outlines a three-part framework for building AI fluency in teams, introduces the concept of everyone managing AI interns, and predicts a shift towards personality-led growth in B2B marketing. Curiosity and persistence are emphasized as key traits for success in this AI-driven landscape.

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INSIGHT

Prompting + Context Is A Superpower

Prompt engineering plus context engineering multiplies output quality dramatically for knowledge workers.
Giving models the right context lets them produce far better, task-specific results.

ADVICE

Make Prompting A Core Team Skill

Teach prompting as a core skill, share examples, and run frequent AI hackathons to accelerate adoption.
Require team members to learn prompting; it's a sink-or-swim skill for modern GTM roles.

ADVICE

Use LLMs To Train Your Prompting

Use ChatGPT memory and custom GPTs as live prompting coaches and model-specific prompt engineers.
Iterate prompts relentlessly and use LLMs to self-evaluate and optimize prompts over time.

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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.