4.4 • 637 Ratings
🗓️ 11 July 2025
⏱️ 76 minutes
🧾️ Download transcript
Kieran Flanagan is the CMO at HubSpot, where he’s led the transformation of their growth strategy from SEO-led to multi-channel and AI-powered. Formerly SVP of Marketing, he helped scale HubSpot’s user base to millions and revenue past $2B. Before HubSpot, he drove breakout growth at Marketo and Salesforce. Kieran is one of the most respected voices in SaaS marketing and a pioneer in growth-driven content strategy.
Agenda:
00:03 – The Death of Growth Teams? Kieran's Wild Prediction
06:44 – AI Innovation Pods: The New Org Structure for Startups
10:18 – Email Personalization That Tripled Conversions
13:21 – From Software Budget to Labor Budget: The Shift is Happening
16:35 – The Big Lie: Why Autonomous Agents Still Suck
19:24 – The Secret Sauce Behind HubSpot’s Email AI Stack
21:44 – Segment-Based Marketing Is Dead. Enter Micro Audiences.
24:15 – Content Collapse: Why Google Organic Is Getting Torched
30:52 – The Future of AI SEO: 1 Product, 100 Pages, Infinite Prompts
33:16 – Memory = Moat: Why ChatGPT Is Becoming Unbeatable
35:46 – Prompt Engineering is the New Coding: Here's How to Win
41:03 – The Death of the Middle Manager Marketer
46:17 – OpenAI vs. Anthropic: Kieran’s $400M Bet
48:00 – Europe Is Falling Behind: The Harsh Truth on Regulation
52:39 – CMO Playbook 2025: Micro-Audiences, Creator-Led, AI at Scale
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0:00.0 | Welcome back to 20 VC with me, Harry Stebbings, and this is a very special episode of 20 Growth, |
0:05.0 | as we welcome back one of my favorite growth minds. So for those that don't know, 20 Growth |
0:09.8 | is the monthly show where we sit down with the best growth leaders to unpack how they think, |
0:15.7 | learn, build the best growth organizations today. And rejoining me in the hot seat is Kieran Flanagan. |
0:22.0 | As I said, I think he's one of the greatest minds in growth today. He runs all things growth |
0:26.5 | and especially AI implementation at HubSpot. Today was a very natural free-flowing conversation |
0:32.2 | that originated from one of his LinkedIn posts, which I loved. And I so appreciate him |
0:36.8 | rejoining me in the hot seat |
0:38.1 | today to really delve into how AI changes the growth landscape as we know it. |
0:43.7 | But before we dive into the show today, Secureframe empowers businesses to build trust with |
0:48.1 | customers by simplifying information security and compliance through AI and automation. |
0:53.4 | Thousands of fast-growing businesses, |
0:55.0 | including NASDA, AngelList, Doodle and Coder, trust Secureframe to expedite their compliance journey |
1:00.7 | for global security and privacy standards, such as SOC2 and ISO-27,1, CMMC, NIST standards, and more. |
1:09.3 | Backed by top-tier investors and corporations like Google and |
1:12.3 | Kleiner Perkins, the company is among Forbes's list of the top 100 startup employers for 2024, |
1:18.2 | G2's best software awards for higher satisfaction products, and a recipient of the 2024 Cybersecurity |
1:24.3 | Excellence Awards, something I definitely never got in school myself. |
1:28.1 | Learn more today at Secureframe.com. |
1:30.7 | Now, let's switch gears to the future of mobile and how one company is turning your screen |
1:35.3 | into real returns. |
1:36.6 | We spend nearly half our waking hours glued to our phones, upwards of 50 hours every week. |
... |
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