Most marketers use AI to write generic emails.

Kieran Flanagan used it to increase sales meetings by 30% and build a “Chief of Staff” that manages his 350-person team.

Kieran is the SVP of Marketing at HubSpot, where he has helped scale the company from 250 to over 7,000 employees.

He is also the co-host of the popular “Marketing Against the Grain” podcast.

In other words, Kieran doesn’t just theorize about AI; he is actively “vibe coding” custom internal tools to overhaul HubSpot’s entire go-to-market motion.

In this episode, Kieran opens his laptop to show exactly how he builds custom AI agents that extract viral talking points from video, automate complex management reporting from Slack, and personalize outreach at massive scale.

Here’s what you’ll learn in this episode:

• The “Vibe Coding” Strategy: Why building your own simple tools beats buying off-the-shelf software.

• 30% More Meetings: The exact email workflow change that drove massive sales efficiency.

• Management Automation: How to use AI to summarize weekly team activity and identify blockers across 350 employees.

• The Death of Prompt Engineering: Why “context grafting” and intent matching are replacing complex prompts.

TIMESTAMPS:

00:00 - Introduction

00:30 - Managing a 350-person team at HubSpot

04:05 - How AI drove a 30% increase in sales meetings

08:07 - Building custom data sets for personalized outreach

14:47 - Demo: Kieran’s custom “Viral Talking Points” tool

21:18 - Why “Vibe Coding” is the future of marketing workflows

25:49 - Turning video transcripts into high-performing LinkedIn posts

30:45 - The evolution of prompt engineering (and why it’s dying)

38:37 - The “Shakespeare Trap” of using AI for feedback

42:30 - Using AI agents for deep research and storytelling

50:28 - Automating management: Summarizing Slack and identifying blockers

59:05 - Why AI makes creativity more valuable, not less

01:02:40 - The #1 trait Kieran looks for when hiring

01:03:15 - Sneak peek: AI agents inside Google Sheets

Where to find Kieran:

LinkedIn: https://www.linkedin.com/in/kieranjflanagan/

X: @searchbrat

Website: https://www.kieranflanagan.io/ , https://www.hubspot.com/

Podcast: @MATGpod

Where to find Tim:

LinkedIn: https://www.linkedin.com/in/timsoulo/

X: @timsoulo

Website: https://www.timsoulo.com/