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

**Annie Pearl** (0:00)
Strategy is really just an integrated set of choices that outline how you're going to win in whatever marketplace you choose. And so a good product strategy is going to answer questions like, what's your winning aspiration?
But maybe more importantly, where are you going to play? What are the markets you're going to go after? What are the segments of those markets? What are the personas in the segments of those markets? And then how are you going to win with a target audience?

**Lenny Rachitsky** (0:26)
Welcome to Lenny's Podcast, where I interview world-class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products. Today, my guest is Annie Pearl. Annie is currently Chief Product Officer at Calendly. Before that, she was Chief Product Officer at Glassdoor. And before that, she was Director of Product Management at Box. She's also a member of Skip, a community for Chief Product Officers, and she's on the board of two different companies. In our conversation, we cover a lot of ground, including how Calendly builds product, how Calendly has grown, including the wild story of how they got their first thousand users, and also how they built a sales team on top of what historically has been a very product-led growth company. Annie also shares a ton of great advice on how to get into product management. I learned a ton from Annie, and I know you'll too. Annie also shares a few killer tips for using Calendly, which I loved. And so with all that, I bring you Annie Pearl for a short word from our wonderful sponsors.
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Annie, welcome to the podcast.

**Annie Pearl** (3:52)
Thanks for having me Lenny, super excited to be here.

**Lenny Rachitsky** (3:55)
I've been a big fan of yours from afar. We've crossed paths a little bit on Reforge, on Twitter, probably been at events that maybe we didn't know each other at yet. So I'm really excited to finally be chatting sort of real life in real time at least.

**Annie Pearl** (4:08)
Me as well.

**Lenny Rachitsky** (4:09)
I've got a Calendly question to kick things off.
It feels like with Calendly, one of the most awkward elements of it is I have to like put the burden on someone else to book a Calendly. So I'm sending a link and I haven't figured out a good way to send it to someone without it coming across like a power move. So my question to you is how do I send a Calendly to someone without it feeling bad?