Ross sits down with Kieran Flanagan, SVP of Marketing at HubSpot, for a deep dive into AI’s impact on SEO, the myth of traffic loss at HubSpot, and how content strategy is evolving in a post-search world.

Kieran unpacks what really happened during the viral “HubSpot traffic drop” controversy and explains why conversions over clicks have always been the priority. They also dive into the shift from backlinks to brand mentions, optimizing for LLMs, and how HubSpot is transforming its internal structure with AI.

Plus: the power of freemium tools, why lazy AI marketers will fail, and how acquisitions like The Hustle are building long-term influence.

‭Show Notes:‬

00:00 – Intro: Did HubSpot Really Lose 80% of Blog Traffic?
02:00 – HubSpot’s Real Metrics: LTV: CAC, Not Just Clicks
04:00 – Google’s AI & the New Era of Search Disruption
06:00 – What Content Will Be Cannibalized by LLMs
08:00 – Influence or Information: Winning with Point of View
10:00 – From Links to Mentions: Co-Citation SEO Strategy
12:00 – Optimizing for LLMs: Citations, Not Just SERPs
14:00 – AI, Brand Authority & The Reputational Layer
17:00 – Tools, Training Sets, and the Battle of Ideas
20:00 – Inside HubSpot’s Media Play: The Hustle, Podcasts & Creators
24:00 – Why Interactive Tools Still Work (If Done Right)
26:00 – Gated Content & Moving the “Free Line”
28:00 – New Team Models: Journalists, Generalists, and Engineers
32:00 – Kieran’s Leadership Framework: Manage Problems, Not People
35:00 – Contrarian Bet: Buying The Hustle & Building Influence
38:00 – Lessons from Zapier vs HubSpot’s Go-To-Market
40:00 – Why Lazy AI Marketers Will Fail
42:00 – Is M&A Still a Growth Lever for HubSpot?
44:00 – Final Thoughts & Where to Follow Kieran

Show Links:‬

Did Hubspot Lose 80% of Blog Traffic?

Contrast Ratio by Siege Media

Interactive Content Data Use

The Hustle by HubSpot

Kieran Flanagan on LinkedIn

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