How the CMO Role is Changing w/ ex-CMO of Calendly Jessica Gilmartin

Jessica Gilmartin was previously the CMO and CRO at Calendly, Head of Revenue Marketing at Asana, and Head of Product Marketing for Wildfire at Google. Today, she works closely with founders and first-time CMOs from pre-revenue through $100M ARR, advising them on everything from hiring, org design to GTM focus and executive communication.

In this episode, we talk about how AI is changing the CMO role and marketing org, where it’s wildly overhyped vs working, and many other topics.

Listen on: YouTube, Spotify or Apple Podcast

We discuss:

* Why CMO + CRO combo roles usually fail

* Why companies now hire CMOs from smaller, scrappier startups

* Where AI is truly useful vs pure hype

* Why random acts of marketing kill momentum

* How Calendly moved from viral PLG to focused enterprise ABM

* The real reason CMOs only last 18 months

* Why taste, courage, and focus still matter more than tools

Connect with Jessica:

* LinkedIn: https://www.linkedin.com/in/jessicagilmartin/

Connect with Finn:

* LinkedIn: https://www.linkedin.com/in/finnthormeier/

* Project 33: https://www.project33.io/

My personal takeaways:

* We’re overvaluing AI right now: Jessica believes we’ll replace most of our day-to-day work with AI in 5-10 years. But right now board members are mandating AI adoption without specific use cases. The reality is AI is making teams 10-20% more efficient and that it works as an enabler, but not as a replacement. The best use cases she’s seeing are data enrichment for lead prioritization, competitive research for product marketing, and using LLMs as synthetic customer panels.

* There are three paths to CMO and CEOs keep hiring wrong. 50% of B2B CMOs come from product marketing, 50% from demand gen, brand CMOs are rare in B2B. CEOs want a unicorn who’s great at both strategic messaging and technical growth. Jessica’s advice: “It’s like asking a backend engineer why they can’t code mobile apps.” Hire for your actual problem right now, not the one you’ll have at $100M.

* The only mistake with bad hires is keeping them. Jessica repeats this constantly to clients, that you will always make bad hires. Or you hire people who were good then but aren’t right now. The mistake afterwards is keeping them too long. When you bring the right person on board, your life gets 10-100x easier.

* Attribution is broken and that’s okay. You’re getting 70-80% accuracy at best. Jessica’s approach is to use the 80-20 rule. Get directionally correct data so teams understand where they can make impact and then work from there. The bigger issue is that companies wait too long to implement basic data and reporting infrastructure.

* Random acts of marketing kill focus. At Calendly, Jessica pivoted the entire team to one thing: repositioning for enterprise customers. Because their CAC was zero for casual users due to viral growth. Marketers hate focus and they want to sprinkle seeds everywhere. But the winning strategy is making big bets, being explicit about trade-offs, and ensuring no one does random acts of marketing.

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