Being Customer Obsessed: Insights from Jessica Gilmartin, Calendly’s CRO
Key Takeaways
- Customer Obsession Is an Operating System: Jessica reframes customer obsession as a daily operating discipline, not a value statement. Calendly's CRO org runs every cross-functional decision through a customer lens.
- Experiment and Learn from Failures: Jessica's mantra: stop framing initiatives as total wins or total losses. Treat each as an experiment with a learning, and the team learns to take more—and smarter—bets.
- Coordinate Customer-Facing Teams as One: Marketing, sales, and CS sit in different orgs at most companies, which fragments the customer experience. Jessica's CRO mandate at Calendly is to make them operate as one motion.
- Diverse Audiences Demand Segmented GTM: Calendly serves SMB self-serve users, mid-market teams, and enterprise IT. Jessica argues each segment needs its own GTM motion—a single playbook always under-serves at least two of them.
- CRO Must Operate Across Marketing, Sales, CS: The modern CRO isn't just the sales leader—it's the operator who owns the full revenue lifecycle. Jessica's role at Calendly models that broader scope.
- Patience Beats Panic in Revenue Cycles: Down quarters trigger panic moves that compound the problem. Jessica's discipline: hold the strategy through noise, adjust execution against leading indicators only.
- Calendly's Bottom-Up Brand Compounds: Calendly's PLG roots gave it a brand most enterprise sellers would kill for. Jessica's job is to layer enterprise motion on top without breaking the bottom-up love.
Key Topics
Experiment and learn from failures, rather than seeing everything as either a total win or a total loss. In this episode,Jessica Gilmartin, CRO of Calendly, shares her perspective on defining go-to-market and the importance of coordinating customer-facing teams like marketing, sales, and customer support.
Join us to explore the challenges of serving diverse audiences and keeping employees focused on the customer through initiatives like a brand manifesto. Let’s just get right in, which is how do you view and define go to market?
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