Lenny's Podcast: Product | Growth | Career

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

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.

01:01:48

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Episode guests

Annie Pearl

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Quick takeaways

Clear product strategy defines target market, priorities, and resource allocation for effective product development.

Transparent resource allocation based on company vision aligns with short to medium-term goals for progress.

Balancing user demands with strategic vision highlights the importance of staying focused on defined strategy.

Deep dives

Clear Product Strategy for Target Market Focus

A key insight from the podcast episode revolves around the importance of having a clear product strategy that focuses on a specific target market. The strategy should define where to play and how to win in that market. This approach helps prioritize work by identifying the markets, segments, and personas to target, ensuring that resources are allocated effectively.

How Calendly Got Their First Thousand Users

02:25

Prioritizing Features

02:59

How Calon Lee Builds Product

01:26

Lessons from a Chief Product Officer

01:16

Intro

4min

Navigating the Etiquette of Scheduling with Calendly

2min

Navigating the Transition to Product Management

3min

Paths to Product Management: Strategies and Insights

2min

Transitioning to Associate Product Manager

17min

Strategic Hiring for Sales in a Growth Transition

2min

Building Bridges: The Synergy Between Product and Sales Teams

3min

Strategic Product Management Uncovered

16min

Focus Wisely: Building a Product-Centric Culture at Calendly

13min

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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: Annie.Pearl@calendly.com

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