⁠David Ebner⁠, president and founder of Content Workshop, is back on the show to talk about AI systems. Content Workshop just launched the ⁠AI Maturity Model⁠, a 10-question survey that benchmarks where your marketing team sits on the AI adoption scale compared to peers. David walks through the five stages, from solo prompting to fully systematized loop factories where agents handle the work and a QA agent named Karen checks everything. He also covers the new ⁠AI marketing courses ⁠Content Workshop is offering and what he is bringing to CyberMarketingCon including MD file giveaways that replace the traditional worksheet and a mysterious third booth.

⁠Gary Survis⁠ is an operating partner at I⁠nsight Partners ⁠who has spent years on both sides of the table, as an operator and as a board member evaluating CMOs. He joins Gianna and Charles on CyberCMO Confidential to talk about what investors want from marketing leaders and why most CMOs miss it. The conversation covers board meetings, CMO interviews, eighteen-month tenure, and why the CMO role is horizontal by nature and what happens when you treat it like it isn’t.

Every year, DataTribe reviews hundreds of early-stage cybersecurity startup submissions for the DataTribe Challenge. Leo Scott, Managing Director and Chief Innovation Officer, sees the market shift before most people do. He joins Gianna ahead of the Cyber Innovation Conference October 26th and 27th in Washington, DC, to talk through this year’s five finalists. The submissions are full of AI. Leo finds the companies one level down more interesting, solving what AI is changing about how attacks happen, how humans get tricked, and how agents get out of control. That is where the 2026 class points. If you want to see them pitch live, the conference is October 26th and 27th in Washington, DC, at ⁠cyberinnovationconference.com⁠.

Tracey Moon is a multi-time CMO and currently leads marketing at BlackCloak, a company that protects executives and their families in their personal lives to prevent corporate breaches. She joined Gianna and Charles on CyberCMO Confidential to talk about why she inserts herself into every part of the business, how she builds credibility before she rolls out her real plan, and why she calls her approach UMA: Unsolicited Moon Advice.

Gianna and Maria are together on the pod to talk about CyberMarketingCon 2026, happening November 15th through 18th in Austin, Texas. The theme this year is Create Your Own Adventure. They talk about sessions, tracks, career stories from past conferences, the buddy program, the WhatsApp group, and why Maria is starting a petition to rename customer marketing to community building. She will have a clipboard. There is also a sloth named Chompers. And Maria has a co-founder discount code for anyone who DMs her.

Lenin Alevski is an AI Security Engineer at Google who spent a week building a text-based cybersecurity survival game in his spare time. ⁠Accidental CISO⁠ puts you in the seat of the first security hire at a company where everything is on fire, and every fraught and heart-pounding decision leads to one of eight endings. He sat down with Gianna to talk about how the game came together, why spec-driven development matters more than vibe coding alone, and what 12,000 players and zero marketing budget taught him about building indie cyber games.

Gianna sits down with Vab Dwivedi, VP of Digital Experience at CrowdStrike, Sandra Liu, a cybersecurity creator with over 200,000 LinkedIn followers, and Eric Becker, Enterprise Account Director at LinkedIn. They covered the CrowdStrike and Sandra Liu creator campaign, why LinkedIn reaches cybersecurity buyers differently than any other platform, how Vab thinks about measurement when the buying journey isn't linear, and why content quality will always matter more than volume.

When David Politis sits down with Gianna and Charles on CyberCMO Confidential, you’re getting something rare: A CEO who loves marketing telling you exactly what he thinks when he watches CMOs operate. Why the CRO wins if you let them, why he stops listening the moment someone says they have a playbook, why the best CMOs he ever wanted to hire became CEOs. And what one engineer just built for 2,000 accounts that made him realize most companies are nowhere near what is now possible.

Yael Grauer won a Pulitzer and got laid off in the same year. She is a freelance investigative reporter covering cybersecurity, privacy, and surveillance. She sat down with Gianna to talk about what companies get wrong when journalists come knocking, why lying in that moment makes everything worse, and what it looks like from the other side of every pitch, every breach response, and every "no comment" that ends up in a story anyway.

Brian Reed has been a CMO six times. He's also watched AI flatten marketing for the past two years and has said so out loud, including in a manifesto he published called AI is Flattening Marketing: Cue the Return of Mad Men. On this CyberCMO Confidential episode, Brian, Gianna, and Charles Gold get into why storytelling and community are the two things AI cannot commoditize. Brian also talks about how he built a “crusty OT guy” persona to validate messaging authenticity, and what community-driven marketing looks like when your buyers wear steel-toe boots and aren’t online very often.

Gemma Goldstein had a quiet Thursday in the office, a domain someone spotted for sale, and an idea. A few short weeks later, Check Point's Exposure Management team had a browser-based arcade game live at exposuremanagement.ai with 11,000 players and a leaderboard. The game launched as part of a broader campaign, and MQLs went up 100% that month. Gemma is careful not to credit the game alone. She and Gianna cover how the campaign came together across multiple channels, what she would do differently now, and how vibe coding an ROI calculator in an hour replaced a project quoted as taking weeks. About Gemma: Gemma Goldstein is Head of Growth for Exposure Management at Check Point, a role she carried over from Cyberint after they were acquired in 2024. Before Cyberint, she spent three years at Envy, a B2B digital marketing agency focused on cybersecurity. Her background spans SEO, paid media, content, and creative strategy.