Lenny's Podcast: Product | Growth | Career

Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)

108 snips

Feb 26, 2023

Annie Pearl, Chief Product Officer at Calendly and former CPO at Glassdoor, discusses her journey in product management and the evolution of Calendly's strategy. She shares insights on transitioning from product-led growth to incorporating a sales team and the importance of strategic hiring. Annie emphasizes mentorship, networking, and practical experience as key to breaking into product roles. She also explores building collaboration between product and sales teams, fostering a user-centric culture, and the challenges in establishing effective Associate Product Manager programs.

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ADVICE

Polite Calendly Scheduling

When sending a Calendly link, offer the recipient a chance to share their availability first.
Reduce friction by suggesting specific times in the email, using Calendly's "add times to email" feature.

ADVICE

Transitioning into Product Management

Consider formal paths like Associate Product Manager (APM) programs at larger companies or applying directly for junior roles.
Explore informal routes such as shadowing PMs, internal transfers through Subject Matter Expert programs, or joining early-stage startups.

ADVICE

Tips for Transitioning to PM

Express interest in product management, partner with PMs, and do some product work on the side.
Search for "associate product manager" on Glassdoor to find open APM roles.

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