Calendly CPO Annie Pearl: Hiring Advice for Product; Calendly's Second Product | 20VC #921

(beeping) Three, two, one, zero. You have now arrived at your destination. Annie, I am so excited for this show. Rarely do I have such a fun chat pre-recording.

(laughs)

Uh, I'm mostly very glad that that wasn't recorded. Um, but, uh, I... Thank you so much for joining me today.

Thank you so much for having me, Harry. Super excited to be here.

I'm excited for this one, I have to say. So let's start with a little bit on you. So you've led some of the most fantastic product orgs, and most recently with Calendly. So how did you get into the world of startups? And then how did you come to Calendly in a very swift, two to three minutes?

Yeah. Absolutely. So, uh, started my career off actually intending to be a lawyer. Uh, and while I was in law school, I actually worked for a management consulting firm, and we specialized in working with startups. So, I was in law school, um, and, uh, assuming I would be a lawyer, but I was getting much more interested in technology and sort of the idea of building companies and products. So, uh, after passing the California bar in 2009, with the intention of being a lawyer, I ended up actually joining the founding team of a startup, uh, called Expert Financial, and we were trying to create a stock market, but for private companies. Um, and so yeah, after raising venture capital money, we hired a bunch of engineers and designers, and I took the role of leading product. So that's really how I got into product management. Um, and my time, you know, at Expert was very much zero to one. How do you get a product off the ground? How do you find product-market fit? All the peaks and valleys of kind of early stage startup life. Uh, and I think that experience really taught me about sort of the power of focus, uh, especially in the early days of finding product-market fit, just how important it is to kind of maniacally focus on solving one problem, uh, and solving it better than any alternative, um, on the market. Um, so yeah, from there I went to-

Thank you for-

Yeah?

Ca- can I ask you quickly, otherwise I forget-

Yeah.

... when you get to my memory's terrible. Um-

Of course.

One pro- one problem, I agree. What's the framework for de- deciding what that one problem is? And does that change over time, what you focus on?

Yeah, I think at the beginning, you really wanna focus on finding where's the sort of most acute, uh, sort of visceral pain points that someone might have within some sort of problem space or some sort of market. Uh, and it may feel really narrow. Uh, it may feel really narrow at the beginning, but I think the mistake that early stage founders take... make, and we certainly s- we, we certainly, uh, struggled with this, uh, at our startup as well, is sort of, um, the shiny objects, right? We came in saying, "We have this really acute pain point around, uh, private market liquidity and being able to, to, to sort of provide private market liquidity to employees and shareholders," given how long it takes to have, you know, some sort of, uh, exit. But then we, you know, said, "Well, let's also do a capital raising platform. Oh, and let's also build a data... uh, a data room. Oh, and let's also build a way for, you know, connections to be made in a networking platform," right? And so, as opposed to just sort of narrowly sticking to this acute pain that we knew was being felt in the market, we sort of decided to build new products far too soon. And I think that's, that's probably my biggest lesson from that experience.