Content and Conversation: Organic Growth Insights from Siege Media

• Beyond Blogging: Building a Media Empire w/ HubSpot’s Kieran Flanagan‬ ‭

  Ross sits down with Kieran Flanagan, SVP of Marketing at HubSpot, for a deep dive into AI’s impact on SEO, content strategy in a post-search world, and the real story behind the "HubSpot traffic drop. Kieran breaks down why conversions—not clicks—have always been at the core of HubSpot’s strategy, how AI is reshaping team structures, and why co-citation and brand authority are the future of SEO. They also cover LLM optimization, the importance of tools in training sets, and what separates influential content from purely informational posts. Plus: Why lazy AI marketers will fail, what The Hustle acquisition means for HubSpot’s media strategy, and how to build long-term influence through POV-driven content. Chapters: 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 Repetitional 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? [https://www.youtube.com/watch?v=tBHoJMOkL6Y](https://www.youtube.com/watch?v=tBHoJMOkL6Y) Contrast Ratio by Siege Media [https://www.siegemedia.com/contrast-ratio](https://www.siegemedia.com/contrast-ratio) Interactive Content Data Use [https://www.siegemedia.com/strategy/content-marketing-trends#interactive-content](https://www.siegemedia.com/strategy/content-marketing-trends#interactive-content) The Hustle by HubSpot [https://blog.hubspot.com/the-hustle/page/1](https://blog.hubspot.com/the-hustle/page/1) Kieran Flanagan on LinkedIn [https://linkedin.com/in/kieranjflanagan](https://linkedin.com/in/kieranjflanagan) 🎧 Subscribe & Follow Subscribe for weekly tips: [https://bit.ly/3dBM61f](https://bit.ly/3dBM61f) iTunes: [https://podcasts.apple.com/us/podcast/content-and-conversation-seo-tips-from-siege-media/id1289467174](https://podcasts.apple.com/us/podcast/content-and-conversation-seo-tips-from-siege-media/id1289467174) Spotify: [https://open.spotify.com/show/1kiaFGXO5UcT2qXVRuXjsM](https://open.spotify.com/show/1kiaFGXO5UcT2qXVRuXjsM) Google Podcasts: [https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9jT3NjUkdLeA](https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9jT3NjUkdLeA) Follow Siege: [http://twitter.com/siegemedia](http://twitter.com/siegemedia) Follow Ross: [http://twitter.com/rosshudgens](http://twitter.com/rosshudgens) Directed by Cara Brown: [https://twitter.com/cararbrown](https://twitter.com/cararbrown) Email Ross: [[email protected]](mailto:[email protected]) #seo #contentmarketing Subscribe today for weekly tips: https://bit.ly/3dBM61f Listen on iTunes: https://podcasts.apple.com/us/podcast/content-and-conversation-seo-tips-from-siege-media/id1289467174 Listen on Spotify: https://open.spotify.com/show/1kiaFGXO5UcT2qXVRuXjsM Listen on Google: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9jT3NjUkdLeA Follow Siege on Twitter: http://twitter.com/siegemedia Follow Ross on Twitter: http://twitter.com/rosshudgens Directed by Cara Brown: https://twitter.com/cararbrown Email Ross: [email protected] #seo | #contentmarketing

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  44:57
• Scaling a Billion Dollar Brand: Lessons from Semrush’s CMO

  Ross sits down with Andrew Warden, CMO of Semrush, for a behind-the-scenes look at how the company has scaled past a billion-dollar valuation through brand innovation, performance marketing, and fearless experimentation. Andrew unpacks how he’s built and structured Semrush’s powerhouse marketing team, why they favor in-house execution over agencies, and how data science and AI are reshaping modern marketing ops. From viral hits like “Be Like Gaby” and “CEO Kiddos," this episode highlights what works—and what doesn’t—when building a global brand. 00:00 – Intro & Nick Eubanks M&A Stories 02:00 – Building the Semrush Marketing Team Structure 04:00 – Why In-House Creative Wins Over Agencies 06:00 – Brand, Digital, and Owned Media: Org Design Explained 08:00 – The Role of Data Science & Marketing Ops at Scale 10:00 – AI Ops: Automating for Speed, Not Just Hype 13:00 – Enterprise vs. SMB: Maintaining Brand Balance 16:00 – Big Wins: “Be Like Gaby” and User-Driven Campaigns 18:00 – When Humor Doesn’t Convert: Learning from the “CEO Kiddos” Flop 21:00 – Why Failure Is Part of the Process at Semrush 24:00 – Scaling Content: Growing the SEO Team from 4 to 40+ 26:00 – Localization: What Works, What Doesn’t 29:00 – Brand vs. Performance: How to Actually Measure Impact 33:00 – Traffic Down, Revenue Up: Moving Beyond Vanity Metrics 36:00 – What SEOs Should Actually Be Goal-ed On 39:00 – AI and Search: The Real Impact on Marketers 41:00 – Semrush’s AI Toolkit & ContentShake Overview 44:00 – The Most Underrated Features in Semrush 47:00 – Prompt Engineering & Early AI Adoption Lessons 48:00 – Conference Announcements & What’s Next for Semrush ContentShake: https://www.semrush.com/apps/contentshake/ Impress your boss commercial: https://www.youtube.com/watch?v=CNCR5XBEM5c Semrush’s most popular campaign: https://www.youtube.com/watch?v=GRHG5CjsPvo Andrew Warden on LinkedIn: https://www.linkedin.com/in/andrewwardenSubscribe today for weekly tips: https://bit.ly/3dBM61f Listen on iTunes: https://podcasts.apple.com/us/podcast/content-and-conversation-seo-tips-from-siege-media/id1289467174 Listen on Spotify: https://open.spotify.com/show/1kiaFGXO5UcT2qXVRuXjsM Listen on Google: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9jT3NjUkdLeA Follow Siege on Twitter: http://twitter.com/siegemedia Follow Ross on Twitter: http://twitter.com/rosshudgens Directed by Cara Brown: https://twitter.com/cararbrown Email Ross: [email protected] #seo | #contentmarketing

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  50:56
• From Content Engine to Freedom Engine w/ Chris Walker

  Chris Walker (CEO of Passetto) joins Ross to talk about personal transformation, scaling through delegation, and why most entrepreneurs are chasing the wrong kind of freedom. Chris shares insights from his month-long sabbatical, including frameworks for creating true independence—beyond just financial freedom—and lessons learned about leadership, agency structure, and internal alignment. Ross and Chris also unpack strategies for delegation, avoiding burnout, client selection, the evolving role of SEO, and how B2B companies should rethink go-to-market in a post-ChatGPT world. 00:00 – Welcome Chris Walker & “The Collision of Worlds” 00:51 – Why Bigger Doesn’t Mean Better (And Why Chris Took a Month Off) 02:05 – The Real Test: Can Your Business Run Without You? 03:09 – 10 Types of Freedom (Beyond Just Financial) 06:01 – Time, Social, Creative, Mission, Health & More 09:10 – Letting Go of the Clients That Drain You 13:07 – Freedom Through Delegation: Fake vs Real 15:05 – Why Firing Someone Might Set Them Free 17:20 – Rethinking Wealth: Why 2x More Money Won’t Make You Happy 20:00 – Breaking Mental Loops Around Growth, Suffering, and “Success” 22:50 – Why Resistance Means You’re Out of Alignment 26:00 – Layoffs, Misalignment, and Making the Hard Call 29:00 – A New Agency Playbook: 10 People, $10M 31:32 – Delegation as a Superpower (And Trap) 34:20 – Hiring Without Job Descriptions 37:00 – How Top Talent Finds You (Not the Other Way Around) 39:01 – From Fake Delegation to Freedom Frameworks 41:00 – Pattern-Matching LinkedIn Content for Real ICP Impact 43:13 – SEO Today: Outdated, Unpersonalized & Being Replaced 46:50 – Why ChatGPT over Google for User Intent 48:10 – The Case for Diversified GTM (and SEO’s Narrow Role) 50:00 – Reframing Search: It’s Not Just Google Anymore 52:20 – Personal Holdings Companies & Managing Partners 54:00 – Why Resume-Perfect Execs Often Underperform 56:00 – Agency Scale: Founder as Visionary, Not CEO 59:00 – Building the Business That Serves Your Life Chris Walker on LinkedIn: https://www.linkedin.com/in/chriswalker171 Chris’s Company, Passetto: https://www.passetto.com Siege Media: https://www.siegemedia.com Subscribe for weekly episodes: https://bit.ly/3dBM61f Listen on iTunes: https://podcasts.apple.com/us/podcast/content-and-conversation-seo-tips-from-siege-media/id1289467174 Listen on Spotify: https://open.spotify.com/show/1kiaFGXO5UcT2qXVRuXjsM Follow Ross on Twitter: https://twitter.com/rosshudgens Follow Siege Media on Twitter: https://twitter.com/siegemedia Directed by Cara Brown: https://twitter.com/cararbrown Email Ross: [email protected] #seo | #contentmarketingSubscribe today for weekly tips: https://bit.ly/3dBM61f Listen on iTunes: https://podcasts.apple.com/us/podcast/content-and-conversation-seo-tips-from-siege-media/id1289467174 Listen on Spotify: https://open.spotify.com/show/1kiaFGXO5UcT2qXVRuXjsM Listen on Google: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9jT3NjUkdLeA Follow Siege on Twitter: http://twitter.com/siegemedia Follow Ross on Twitter: http://twitter.com/rosshudgens Directed by Cara Brown: https://twitter.com/cararbrown Email Ross: [email protected] #seo | #contentmarketing

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  49:01
• The SEO Behind Zillow’s 1 Billion‬‭ Visits/Year w/ Kristan Bauer‬‭

  Kristan Bauer returns for a deep dive into the technical and organizational SEO strategies that helped Zillow grow to nearly 2 billion annual visits. She shares tactical insights on enterprise SEO at scale, including testing frameworks, internal collaboration, indexing strategies, and what it takes to lead with executive presence in a high-stakes environment. Ross and Kristan also unpack the challenges of long-tail targeting, structuring an SEO team for success, and how to know when it’s time to build your own SEO testing platform. 00:00 – Welcome Back Kristan & The Zillow SEO Journey00:34 – From Agency to Zillow: What Made Zillow’s Traffic Explode01:09 – How Zillow Reached Nearly 2 Billion Visits/Year03:23 – The Hidden SEO Power of Off-Market Listings04:23 – Internal Linking Tactics to Boost Indexing06:52 – Long-Tail Dynamic Pages from Listing Descriptions08:44 – Managing Page Quality in Long-Tail SEO10:21 – When & Why Zillow Invested in an SEO Testing Platform12:09 – How SEO Was Structured at Zillow (and Why It Worked)13:58 – Quarterly Planning + Executive-Level SEO Visibility15:05 – One-on-One Collaboration With Other Channel Leads17:10 – Building a Culture of Shared Ownership Around SEO18:56 – Risk Management via SEO Testing Platforms20:39 – Why Testing Is a Must at Enterprise Scale22:51 – How Zillow Prioritized Smart Resource Allocation24:41 – How to Know When It’s Time to Build a Platform26:41 – Structuring SEO Inside Product vs. Marketing30:06 – How Cross-Team SEO Works at the Enterprise Level32:21 – Building Executive Presence & Communicating Up34:05 – Wins, Challenges & Transparent SEO Reporting36:00 – SEO Summits with Airbnb, Yelp, TripAdvisor & More41:00 – Final Lessons: Communication, Creativity & Big Rocks Kristan’s Website: https://www.kristanbauer.comKristan on LinkedIn: https://www.linkedin.com/in/kristandaubleOur Previous Episode on Enterprise Real Estate SEO: https://www.siegemedia.com/conversation/kristan-bauer Subscribe today for weekly tips: https://bit.ly/3dBM61f Listen on iTunes: https://podcasts.apple.com/us/podcast/content-and-conversation-seo-tips-from-siege-media/id1289467174 Listen on Spotify: https://open.spotify.com/show/1kiaFGXO5UcT2qXVRuXjsM Listen on Google: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9jT3NjUkdLeA Follow Siege on Twitter: http://twitter.com/siegemedia Follow Ross on Twitter: http://twitter.com/rosshudgens Directed by Cara Brown: https://twitter.com/cararbrown Email Ross: [email protected] #seo | #contentmarketing

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  43:14
• Is Technical SEO Dying? + What to Do Instead w/ Eli Schwartz

  Ross welcomes Eli Schwartz, author of‬‭ Product-Led‬‭ SEO‬‭ , to unpack the evolving‬ role of SEO in a world shaped by AI, shifting perceptions, and organizational‬ challenges.‬‭Eli dives into why SEO is being deprioritized, what companies are getting wrong,‬ and how product-led SEO is the path forward.‬‭They cover layoffs, agency churn, the role of growth teams, and why most‬ companies‬‭ shouldn’t‬‭ do SEO at all.‬ ‭ Show Notes:‬‭ 00:00 Welcome Back Eli & The Current Pulse on Search‬‭ 00:53 Marketing Layoffs & Volatility in SEO‬‭ 02:31 Why SEO Struggles to Defend Its Value‬‭ 05:49 AI Search vs Traditional SEO — What Actually Changes?‬‭ 07:58 Are We Just Rebranding SEO?‬‭ 09:27 Visibility, Links & Human-Like Search Engines‬‭ 12:50 The Problem With “AI SEO” Hype‬‭ 14:45 Why Edge Case SEO Will Die Fast‬‭ 18:19 Why “Technical SEO” Isn’t a Moat Anymore‬‭ 22:06 The AI Content Misstep: Spam at Scale‬‭ 24:27 The New SEO: Blending Human + AI + Product‬‭ 28:11 Your Product Has to Be Good Now — Period‬‭ 29:20 Revisiting the Book: What Eli Would Update‬‭ 30:20 The Spicy Take: Most Companies Shouldn’t Do SEO‬‭ 35:03 How to Evaluate if SEO is Right for You‬‭ 38:45 The “Tax Preparer” Problem With Agencies‬‭ 41:06 If You’ve Fired 3 SEO Agencies… It’s You‬‭ 43:20 The SEO Funnel Needs the Right Org Buy-In‬‭ 46:01 Growth & Product Titles Are the Key‬‭ 47:28 The Sales Enablement Side of SEO‬‭ 50:30 Content Strategy vs Keyword Volume Obsession‬‭ 51:40 The Non-Apocalypse of AI‬‭ 55:04 The Real AI Shift Will Be Gradual‬‭ 56:01 How to Actually Execute Product SEO‬‭ 59:49 Final Thoughts & Where to Follow Eli‬‭Show Links:‬Eli’s Newsletter:‬‭ https://www.productledseo.com/‬Eli’s Book on Amazon:‬‭ https://www.amazon.com/dp/B091D572ZL‬Eli on LinkedIn:‬‭ https://www.linkedin.com/in/schwartze‬‭‭‭ Subscribe today for weekly tips: https://bit.ly/3dBM61f Listen on iTunes: https://podcasts.apple.com/us/podcast/content-and-conversation-seo-tips-from-siege-media/id1289467174 Listen on Spotify: https://open.spotify.com/show/1kiaFGXO5UcT2qXVRuXjsM Listen on Google: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9jT3NjUkdLeA Follow Siege on Twitter: http://twitter.com/siegemedia Follow Ross on Twitter: http://twitter.com/rosshudgens Directed by Cara Brown: https://twitter.com/cararbrown Email Ross: [email protected] #seo | #contentmarketing

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  48:07

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