Lenny's Podcast: Product | Career | Growth

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

February 26, 2023

AI Summary

5 min read

Annie Pearl, Calendly's chief product officer, explains the company's product strategy, development processes, and shift from pure product-led growth (PLG) to incorporating sales-led growth, drawing on experiences at Glassdoor and Box to refine focus on core users.

Product Strategy Framework

Calendly uses a framework from Playing to Win defining strategy as choices on winning aspiration (best place to schedule, prepare for, and follow up on external meetings), where to play (sales, recruiting, customer success teams), and how to win. This narrows prioritization from broad horizontal users (freelancers, educators) to ideal customer profiles (ICPs) in organizations, enabling teams to say no—e.g., skipping Venmo integration for solopreneurs. Horizons guide resource allocation: year 1 was 70% on core scheduling (horizon 1), shifting to 30/60/10 across three horizons by year 3.

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What you'll learn

1 *(04:09) **Calendly Usage Tips**
2 *(06:04) **Breaking into Product Management**
3 *(13:27) **Calendly Product Org Structure**
4 *(19:07) **OKRs and Strategy Evolution**
5 *(21:20) **Narrowing Target Market and Prioritization**
6 *(23:45) **PLG to Sales-Led Growth Transition**
7 *(32:16) **Product Development and Planning Process**

+ Full timestamped outline available in the app

Show Notes

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Annie Pearl is the Chief Product Officer at Calendly. Previously, she was Chief Product Officer at Glassdoor, as well as Director of Product Management at Box. She was named one of the most influential women in Bay Area business by the San Francisco Business Times. In today’s episode, Annie shares three paths into product management and advice on how to get your foot in the door. She also gives us an inside look at how Calendly’s product teams are structured, how they transitioned from solely PLG to adding a sales team and unlocking new growth levers, how they do planning, and much more.

Find the full transcript here: https://www.lennysnewsletter.com/p/behind-the-scenes-of-calendlys-rapid

Where to find Annie Pearl:

• LinkedIn: https://www.linkedin.com/in/anniepearl/

• Email: [email protected]

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• Twitter: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

Referenced:

• How to send a calendar invite with Calendly: https://calendly.com/blog/how-to-send-a-calendar-invite

• Google’s APM program: https://careers.google.com/programs/apm/

• The 15 Best Associate and Rotational Product Manager Programs: https://medium.com/agileinsider/product-management-digest-apm-3c2631683139

• Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X/

• Confluence: https://www.atlassian.c