Behind the scenes of Calendly’s rapid growth

Annie Pearl, chief product officer at Calendly and formerly CPO at Glassdoor and director of product at Fox, discusses how Calendly builds product, how it grew from a free viral tool into a company adding a sales motion, and how people can break into product management. The conversation also covers strategy, OKRs, roadmapping, and team culture.

01Key learnings

• When sharing a scheduling link, first invite the other person to share their availability, and paste your open times directly into the email to reduce friction.
• Break into product via internal transfer: show curiosity, help with product work on the side, and build relationships with PMs, since this path brought Pearl many of her strongest hires.
• Start from a clear product strategy that defines where you play and where you don't, including the markets, segments, and personas you will target.
• Narrowing to a target persona is hard but essential; saying no to features like niche integrations lets teams deliver great value to the people who matter most.
• Commit to dates only for work within your control: commit to discovery, then solutioning, then build, and estimate delivery only once the solution is known.
• Early sales hires for a product-led company should fit the inbound, PQL-driven motion and the buyer persona (department heads), not outbound hunters selling to CIOs.
• Treat the sales and go-to-market teams as a major source of customer insight, since they talk to far more customers than any single PM can.
• Connect OKRs top to bottom with tight dependency mapping across the company, rather than leaving product OKRs siloed from other departments.

02Frameworks mentioned

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.