Measuring AI ROI in GTM

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

Brought to you by: Mutiny

Are you a B2B Marketer running campaigns for target accounts? Then you know the struggle: tedious and manual processes, endless delays to get things live, and sales feeling like you’re not doing enough.

That’s where Mutiny comes in. Mutiny is the fastest place to launch breakthrough campaigns for your target accounts. 

AI agents research your accounts, build personalized landing pages, and scale everything from LinkedIn ads to sales handoffs, all in one seamless workflow. No more stitching tools together. Just smarter, more impactful campaigns powered by real data. Launch in days, not weeks.

See why teams who use Mutiny generate 3X more account engagement.

Book a demo at mutinyhq.com

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.