The GTMnow Podcast

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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