Feb. 26, 2023

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

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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.


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/



• 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/

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• Nikhyl Singhal on LinkedIn: https://www.linkedin.com/in/nikhyl/

Good to Great: Why Some Companies Make the Leap and Others Don’t: https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996

Hooked: How to Build Habit-Forming Products: https://www.amazon.com/Hooked-How-Build-Habit-Forming-Products/dp/0241184835/

20VC podcast: https://www.thetwentyminutevc.com/

Sing 2 on Netflix: https://www.netflix.com/title/81475311

• Miro: https://miro.com/


In this episode, we cover:

(00:00) Annie’s background

(03:50) How to send a Calendly invite without feeling awkward

(06:04) How to transition to product work from a non-technical career

(09:53) APM programs

(10:52) The characteristics of internal-transfer PMs

(13:26) How Calendly structures product teams 

(14:57) Why Annie hired a Head of Design

(16:58) How Calendly structures product teams

(19:07) OKRs at Calendly

(21:02) Changes made at Calendly to improve execution and shipping

(22:45) The challenges with narrowing Calendly’s customer base and adding sales 

(25:21) Where 70% of new Calendly users come from

(26:17) The transition from PLG to sales

(29:23) How to build a great relationship with your sales team

(31:52) Planning and prioritization at Calendly

(38:14) Strategy documents at Calendly

(39:39) Calendly’s product stack

(40:21) How Calendly got their first 1,000 users 

(43:36) The surprising new growth levers at Calendly

(46:05) Fun traditions

(48:43) “Focus wisely” and other aspects of Calendly’s culture

(52:07) Learnings from Box and Glassdoor

(54:57) The Skip Community

(58:10) Lightning round


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Annie Pearl (00:00:00):

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 (00:00:27):

Welcome to Lenny's Podcast where I interview world-class product leaders and growth experts to learn from their hard one 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 Fox. 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 1,000 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 through a short word from our wonderful sponsors.


Today's episode is brought to you by Miro, an online collaborative whiteboard that's designed specifically for teams like yours. I have a quick request. Head on over to my Miro board at miro.com/lenny and let me know which guests you'd want me to have on this year. I've already gotten a bunch of great suggestions, which you'll see when you go there, so just keep it coming. And while you're on the Miro board, I encourage you to play around with the tool. It's a great shared space to capture ideas, get feedback, and collaborate with your colleagues on anything that you're working on.


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Annie, welcome to the podcast.

Annie Pearl (00:03:53):

Thanks for having me, Lenny. Super excited to be here.

Lenny (00:03:55):

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, real life, in real time, at least.

Annie Pearl (00:04:09):

Me as well.

Lenny (00:04:09):

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 put the burden on someone else to book at 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?

Annie Pearl (00:04:31):

All right, well I love this question to kick us off. We actually have a whole blog post about this if you're curious to learn more.

Lenny (00:04:31):

Oh, okay.

Annie Pearl (00:04:37):

But I think that at a high level, I think I recommend first really just kind of opening the door for the person you're trying to schedule time with to share their availability first. So instead of just sending the link, I usually start the email with something like looking forward to connecting, feel free to share, sometimes you're available or if easier, you can choose to find time on my calendar using the Calendly link here. So, opening the door to let them choose before you offer up your Calendly link, I think is a little bit of a subtle way to let them take the lead if they want.


And the second piece I would recommend too is once you opened that door, you can further reduce the effort on the recipient by adding times you're available directly in the email. So, when you go to share a Calendly link, there's an option to add times to email and you can then just paste those directly into the email you're creating, so that reduces yet another sort of point of friction to ask the user to click the link and get taken to Calendly. So, opening the door and then adding times to email are two things that I do to really make sure that it's not awkward and it doesn't put the burden on the other person.

Lenny (00:05:39):

That is awesome advice. That first one is what I ended up doing actually. That's really interesting where you don't send the link immediately. You first just ask, "Hey, send me your Calendly." And actually, I always say, "Send me your Calendly." I assume that's what they're using. That's kind of funny.

Annie Pearl (00:05:53):


Lenny (00:05:53):

I don't even know what else is out there.

Annie Pearl (00:05:54):

That's good. That's what we like to hear.

Lenny (00:05:56):

Yeah, absolutely. It's like its own word now. Okay, that was awesome. So, there's this already actionable advice for anyone listening.

Annie Pearl (00:06:03):


Lenny (00:06:04):

Transitioning a little bit to product, the main focus of chat, you transitioned into product from being a lawyer. You told me at one point that a lot of people ask you for advice about how to transition into product from other functions, especially non-technical functions as someone without a technical background. So, what advice do you give people when they ask you how to transition into a product role?

Annie Pearl (00:06:25):

I got what I'll call lucky, which is I kind of stumbled into product management after law school, joined the founding team of a startup and ended up doing product management there. But when I think about folks who are looking to get in their product management, I think there's really two paths. I think one is more formal in nature. There are associate product manager programs out there and many scaled companies, Google, Meta. All have APM programs that you can formally apply to. And actually, when we were at Box, much earlier stage company than either of those companies I just mentioned, we actually created an APM program to help grow our bench of more junior PM. So, I think you can actually find APM programs even at smaller, earlier stage companies than even kind of big tech. So that's one, it's just formal APM programs.


I think another "more formal" way to get into PM is really by just directly applying to a junior PM role where there's no expectation of any sort of experience. I've usually seen this work best when you're already working somewhere in some product adjacency. Maybe you're in customer support, implementation, or maybe you're a sales engineer. But you can look at the internal job board and find junior PM roles that are posted and that's one way to make the move. So that's kind of on the formal side like APM programs and just applying via internal job boards.


I think on the informal side, really two suggestions here. The first one is to seek out opportunities to shadow or partner closely with a product manager and maybe even offer to take on some work. So, some of the best PMs that I've brought over to product from other functions, they really start by expressing interest in product and then start partnering closely with the product manager and maybe even doing a little bit of product work before they make that transition.


And one tactical suggestion is there's oftentimes companies will have subject matter expert programs where they want to pair someone from a go-to-market function with a certain product squad or a certain product area. And so that's becoming a SME. It allows you to really get more involved and embedded into the product team. So, that's one suggestion. And then maybe last one is just the path I did, which is joining an early stage startup. There's really usually an expectation that everyone's going to get their hands dirty doing a lot of different things. And so, I think that's one way where you might have an opportunity to try product management if you end up joining an early stage company.

Lenny (00:08:38):

So, maybe it was four, maybe it was more paths that you described. Join APM program. What was the second one again?

Annie Pearl (00:08:45):

Internal job board apply, when you're in the company.

Lenny (00:08:48):

As just like a junior PM. Two is, find someone that mentors you and helps you start doing the role. And is that internal? Is that the internal transfer app?

Annie Pearl (00:08:58):

Yeah, exactly.

Lenny (00:08:58):


Annie Pearl (00:08:59):

And then, another flavor of that is sometimes companies will have these SME programs.

Lenny (00:09:03):

What is a SME program?

Annie Pearl (00:09:05):

Subject matter expert. So, you'll say, "Hey, I want to make sure we have subject matter expert in our CS team on this area of the product." And they'll partner really closely with the product manager and designer within that area.

Lenny (00:09:16):

Got it. And then the fourth bucket is, join a startup, start doing PM work and then you end up being a PM.

Annie Pearl (00:09:21):

You got it.

Lenny (00:09:21):

Which of those four do you find most common? And would you push people in one direction or another?

Annie Pearl (00:09:26):

Yeah, I've brought a lot of folks over internally for the path of someone's really interested in product, they express they're interested, they want to help, they want to learn, they're eager, they're curious. And so, they make that really well known and they're even willing to do some work on the side to help out and really show and demonstrate the skills before they have the job. So, I've seen that one to actually probably bring the most folks over in my role in terms of being on the product leadership side.

Lenny (00:09:53):

On the APM program route, are there any APM programs you recommend? Because I'm sure people hear this and they're like, "Yeah, but I don't know where to apply. I don't know which ones are good." I don't know if you have a list, but just what comes to mind as APM programs to go pursue?

Annie Pearl (00:10:05):

The folks who started it all was Google, with the Google APM program. And Meta obviously has a pretty strong robust APM program. But as I mentioned around Box, I think those are obviously very, very competitive and most people want to get into them. It may be better to try and find a company like Box or a company that's a bit earlier stage, not as scaled to think about looking at those APM programs. And I'm sure if you want to, go to glassdoor.com where I used to work at Glassdoor, so had to throw that in there. You could search for associate product manager and I think you'll find a whole host of open roles that you might be able to apply to.

Lenny (00:10:39):

That is a cool tip. I haven't heard of that. Go to Glassdoor and search for APM. So, you search for companies that have an APM title.

Annie Pearl (00:10:45):

Yes. You could just use associate product manager and you'll see all the open jobs out there and then go apply to them.

Lenny (00:10:50):

That's cool. Okay, good tip. What I find, and you mentioned this the best, if you have the option is internal transfer. If you're just like another function, you find someone that can help you move into the role.

Annie Pearl (00:11:01):

You have the relationships, you can show your work really well. The other thing I would say is when I think about folks who have successfully transferred over, I think they tend to have a couple of characteristics. They're usually very curious, they tend to be really passionate about the product and solving customer problems. And sometimes, they've even tinkered with a side project as a way to hone their PM skills. So, I think as you're thinking about making that transition, those types of characteristics really showing eagerness and interest in the product itself and solving customer problems are also great ways to get noticed and increase your chances.

Lenny (00:11:36):

Why do you think it is that not more companies have an APM program? It feels like such a win for so many people. Why is it just so rare?

Annie Pearl (00:11:42):

Yeah, I think when we built this at Box, so drawing on that experience, it was a lot of work. If you're going to do it, you want to do it really well and you want to create an environment where you can help the associate product managers be successful, the goal is to ultimately graduate everyone from the APM program into being a product manager. And so, I think it takes a lot of intentionality and for us, it took a lot of work. We had to make sure we had clarity around the interview process. We had to make sure we had clarity around expectations in the role. We wanted to have a training element.


We wanted to make sure that, again, we're setting people up for success. So, I think companies have to be at a stage of scale where they can really invest and they have the excess capacity to build the program in a way. I think that's going to help make sure everyone who comes through it has a chance at really learning, growing and ultimately being successful.

Lenny (00:12:33):

That's the same thing we found at Airbnb. There's a PM that was so excited to make the APM program and it just never really happens. It just takes so much work. And to your point, you have to set up for success. You want to make sure there's clear paths and you upgrade to a regular PM and have the interview.

Annie Pearl (00:12:49):

And are we doing, is this really an APM program for internal folks? Is this external? Are we going to be really trying to promote this? So, I think there's a lot of ancillary activities around the actual program itself that have to be taken into consideration to make sure that it is actually very successful.

Lenny (00:13:06):

Yeah. Maybe a last point we should probably imagine you agree with is generally just hard to get into product management. That's like the default. There's just not that many roles at companies versus say, engineers or some other functions.

Annie Pearl (00:13:17):


Lenny (00:13:17):

So, I think that's just like there are not that many roles. It's a difficult role to break into, but these are the ways you can do it if you actually want to.

Annie Pearl (00:13:17):

That's right. Yep.

Lenny (00:13:27):

Okay. So, I want to transition a little bit to talking about Calendly.

Annie Pearl (00:13:29):


Lenny (00:13:29):

There are two areas I want to go. One is just how do you build product at Calendly? What have you learned about product development and team building? And then two, talk about how Calendly grows and what you've learned about growing a product like Calendly. It's such an interesting product, especially from a growth perspective. So, to start on just how product is built at Calendly, just a little context. How many product managers are there and how many PMs are there? How many people total, roughly? Yeah, just to give us a little bit of [inaudible 00:13:57].

Annie Pearl (00:13:56):

Let's see, when I joined about two years ago, I think the company was about 150 people and I think we're about 600 now. And then the product team, there were about 15 product managers and designers when I joined again about two years ago, and I think we're around 60 this year.

Lenny (00:14:08):

Wow. So, 60 product managers.

Annie Pearl (00:14:14):

Product managers, designers, and a research team. Yeah.

Lenny (00:14:16):

Got it. What about just PMs?

Annie Pearl (00:14:20):

PMs probably, my guess is 20.

Lenny (00:14:23):


Annie Pearl (00:14:24):

Twenty-ish. Yeah.

Lenny (00:14:25):

Cool. And then, can you talk about how the product team is structured roughly? If you think about a tree, [inaudible 00:14:30] tree.

Annie Pearl (00:14:30):

Yeah. So, as I mentioned, we've got product managers, we have designers, we have a research team, and then product operations. And then, on my product leadership team, we have head of design, head of research, head of product operations. And then, within the product management team, I have leaders across core, across enterprise and platform.

Lenny (00:14:50):

Got it. So, you manage the design team and engineering team, you said?

Annie Pearl (00:14:54):

Not engineering. Design, product and research. Yeah.

Lenny (00:14:56):

Got it. Something that I find is one of the big differences between product orgs is design reporting up to a product leader versus not. What's the rationale there? And then has Calendly tried a different approach?

Annie Pearl (00:15:08):

Yeah. So, when I was at Glassdoor in the CPO role, I had the opportunity to lead design for the first time. So, coming into Calendly, I had led both product and design as well as research. And so, I think it made sense given I'd already done it once to keep that structure coming into Calendly. I think at the end of the day, the real benefit of the structure is really to say at the end, we want to be thinking about everything we're doing through the lens of the end-to-end user experience. And so, if we have product managers who are really prioritizing the problems we're going to go after, and we've got designers who are really trying to think about how do we bring solutions to life to solve those problems, having both of those functions roll into one person just really allows us to think more holistically around the end-to-end user experience.


So, certainly, it can work where you have product and design reporting into different leaders that ultimately report into the CEO, but when you get to this level of scale from just a pure people management, but also just the scale of the business, you know often see this consolidation where product and design start to roll into one leader. And at least in my experience, I think it can help ensure that all the different pieces of work are integrated well together and ultimately deliver a better experience for customers.

Lenny (00:16:23):

So, it sounds like before you joined it wasn't like that. And if that's true, was there something that improved with that shift?

Annie Pearl (00:16:29):

So, the structure was there that way. At that time, we didn't have a head of design, so we had a lot of really great individual contributors and who had been, many of whom had been with the company for quite some time and really contributed to the great user experience that existed in the product. But we didn't have a design leader. So, one of the first leadership hires I made was to bring in a head of design to really build out that function. And then, that head of design is a peer partnering with the different heads of products across the product management organization as well.

Lenny (00:16:59):

What about in terms of the structure, whatever you can share one level below, how do you structure teams? Is it around outcomes? Is it around features of the product? Is it around type of persona? How do you think about that?

Annie Pearl (00:17:13):

Yeah, yeah. So, we have a core team who's really responsible for the core end to-end user experience. In many ways, they're both doing feature development and then they're also doing growth work. So, they're thinking about how do we build new features and functionalities to help our core personas, which is typically folks who are in sales, recruiting and customer success. So, anyone in an externally facing role, we're really trying to help them do their jobs better. So, the core team's thinking about features and functionalities to really help our core end user persona. And then growth work to think about the PLG funnel, everything from acquisition, activation, conversion, and retention. So, that's one group.


And then, second group is our "enterprise group." And they're really thinking about two different personas. One is the IT admin, the person who needs to make sure that Calendly is secure and that they have all the reporting mechanisms to be able to manage their account and all the tools to manage users and groups at scale. And the second piece of that is also departmental leaders. So as Calendly selling into or being used by a sales organization, the head of sales is not the IT admin, but they are a Teams admin who needs to manage their organization within Calendly. So, the enterprise group really thinks both about the admin, but also sort of the departments and how do we better serve departments.


And then lastly, we have a platform team who's really thinking about how do we embed Calendly into the business processes of the organizations that we support and that we provide our product into. And so, that's everything from partnerships and integrations to our APIs.

Lenny (00:18:46):

Interesting. So, it's like problem focused/persona focused. Who are you trying to sell it to?

Annie Pearl (00:18:54):

That's right, that's right. Yeah, trying to sell it to, and then the persona of who's going to be using the functionality. And then, really having those teams hone and own those personas as they're developing functionality within the product.

Lenny (00:19:07):

What's your take on OKRs? Do you all use OKRs in some form?

Annie Pearl (00:19:11):

Yes, we do. We use OKRs both at the company level. So, we have three main OKRs that we're focused on for this year, for example, across the whole company. And then we have department level OKRs, many of which are in support of the company level OKRs, but then there's some additional things that we'll be doing at the department level, for example, that aren't going to show up at the company level. So yeah, we use them both at the company as well as on the product side.

Lenny (00:19:34):

Is there anything you've learned about making OKRs work? People love them. People hate them.

Annie Pearl (00:19:39):


Lenny (00:19:39):

Is there something you do to make OKRs work? Something you've changed, something you've learned over time in how to work with OKRs?

Annie Pearl (00:19:44):

Yeah. When I first joined, I'd say we didn't have this muscle well built out. We didn't really have a clear product strategy at the time or clear OKRs guiding the work. And so, there was a lot of great work happening, but it really was unclear how it all fit together or how we were going to measure success in that work. So that was a first phase. I think the second phase for us was we developed a product strategy. We then had product team OKRs that corresponded to that product strategy, but they were really contained to the product team and each department across the organization had their own kind of siloed OKRs.

[NEW_PARAGRAPH]And then, phase three, where really, I'd say we headed into this year, we have a really clear set, as I mentioned, of company OKRs and then in these really tightly integrated plans across the company around how we're going to support the key results and ultimately deliver on the objectives. And this has been a really incredible transformation of dependency mapping, being able to make sure that we're pulling all the levers across the organization to drive our most important objective.


So, I think it's just the kind of maturing of the business from almost no OKRs to product team OKRs to now company OKRs in a really tight planning process to make sure there's a lot of integration across the company to support what we need to do as a business.

Lenny (00:21:01):

So, what I'm hearing is one of the biggest changes in learnings was to connect OKRs across from the top to the bottom, right?

Annie Pearl (00:21:08):

Absolutely. Absolutely.

Lenny (00:21:09):

Is there anything else that has made a big impact on your ability to build and ship and execute as a company in terms of changes you've made in terms of how the company and how the teams build?

Annie Pearl (00:21:20):

I think one of the biggest changes that we've made, when I first joined, again, we had a product that served a lot of horizontal users. We help solo users who are freelancers, consultants. We help sales teams, we help recruiting teams, we help customer success, we help folks in education. So, we had a very broad user base. And what that means is that product managers in particular are I think had a really hard time prioritizing. At any point in time, it was really difficult to say, should I do work on feature A or for feature B without that clarity? And so, I think one of the most impactful things we did pretty early on in my tenure here was to hone in on our overall product strategy, but a poor piece of that being what's the actual market we're going after? What are the segments of that market? Who are the personas within the segments of that market?


And so, we've made a pretty clear distinction now that while a lot of the feature work that we'll do to support our target personas of sales teams, customer success teams and recruiting teams will impact folks who are not in those personas. Those are the core ICPs that we're going after. And so, historically, that would've been always a sort of trade off decision and a question. And now I think we have a lot of rigor around who our target market and then persona we're going after. And so, teams can use that to prioritize and also just deliver better value for those users.

Lenny (00:22:45):

So, it sounds like the biggest unlock and one of the biggest unlocks for making the team more efficient, move faster, make decisions quicker, is narrowing in on exactly who you're going to be selling to.

Annie Pearl (00:22:55):

I think it's one of the harder things for companies to do. So, it sounds relatively easy, and I think most companies believe that they have clarity around this. But then when you go down into the weeds of asking someone who's product manager or a designer, I don't know that it's always as clear because there's always a bit of a hesitation to say no, right? And the idea of saying no is scary. When in reality, the ability to say no is going to allow you to make sure you're building something that's going to be amazing for the people that matter most and not something that's going to be average or okay for a lot of different people.

Lenny (00:23:28):

Was there anything that was really hard about actually executing that, convincing people we're going to narrow and not worry about these people and any lessons from going through that process? Because I imagine a lot of founders listening are like, "Oh, that sounds we should be doing this, but oh man, we're leaving all this money on the table, people are going to be pissed."

Annie Pearl (00:23:45):

Yeah, I think it's a pretty big cultural shift. So, some of this intersects with the shift from product led growth to adding in a sales motion. So, when I joined Calendly, all of our ARR came from our PLG channel. We didn't have a sales team, we just hired a CRO who was going to build out a sales team. And so, in that world, the way you think about product, the way you think about processes, even the people you have on the team are tailored to that business model. And then, as we sort of moved up market and have now explicitly started to go after teams of users and departments of users and organizations of larger scale, everything about people, process, and product all changes.

[NEW_PARAGRAPH]I think I touched on culture because I think that's pervasive across the entire organization. The way that things get done has to be highly integrated versus can be a bit more siloed when you're just sort of the self-service PLG business that in many ways runs itself through the product being well optimized. So, there's a lot of process change that needs to happen, the type of people that you need to bring into the organization, that changes as you layer in the new selling motion. And then the product itself of course has to change.


So, I guess let's just say the example of PLG and SLG or the direct selling motion is tied in to your question around what are the things that need to change in order to get clear on your target user? And I think it's highly cultural in nature across people, across process, and then obviously across the actual product itself.

Lenny (00:25:15):

I have a whole bunch of questions about how Calendly grows and maybe we just get into some of the stuff because I imagine a lot of people are interested. First, let me ask this. I imagine Calendly mostly grows through, I sign up for Calendly, they send it to everyone when I book a meeting and they're like, "Oh, what is this?" And they're like, "Oh, cool, I'm going to use this." And then they start using, it spreads, and then sales eventually finds people at a company that are using it a lot and tries to get the whole company in it. Is that roughly right?

Annie Pearl (00:25:39):

Yeah. Seventy percent of our signups come through that viral loop that you referred to. And then, of those signups, then they're usually solo users and then they start to invite team members in and then the team starts using Calendly and then usually the head of that team either inbounds to us or we have some sort of PQL data to know we should go after that team lead to try and have a conversation around expanding Calendly across their entire organization.

Lenny (00:26:05):

And PQL, product qualified lead, right?

Annie Pearl (00:26:08):

You got it. Yep.

Lenny (00:26:08):

Wow, what a loop. What a magical way to grow that everybody wishes they could have.

Annie Pearl (00:26:14):

It's pretty incredible, I will say.

Lenny (00:26:16):

Oh man. Okay, so going back to the question. When did Calendly hire their first salesperson, like any learnings about just how to start down that road once you start a product?

Annie Pearl (00:26:25):

Yeah. As I mentioned, when I joined two years ago, we just hired our first CRO and the PLG business really represented 99% of our ARR. And then, over the last two years, we've scaled the sales team in our SLG motion. Our sales led growth motion now represents about 20% of our ARR and it's actually the fastest growing segment of the business. I think there's probably two things I would touch on in terms of early sales hires. I think the first is, when you're making that transition from PLG to adding in the sales led motion, because you're starting from PLG, it's tends to be much more inbound in nature. You've got these sales reps who are working leads who have usually proactively reached out interested or as we mentioned PQLs. They have data to tell them that this is someone who has usage within their team, and therefore, we should reach out.


And so, that's a very different profile of a sales team member than you might need after you need to pursue more of a heavy outbound motion, more of a hunter profile than a grower profile. So, I think that's the first piece is just make sure you think about the motion when you're moving towards a sales led model. In those early days, it's more inbound in nature, and so the type of sales reps you might need are not necessarily going to be outbound, heavy kind of hunting sales reps.

Lenny (00:27:46):

Just one quick question on that actually, because that's really interesting. I don't know how involved you are in hiring these folks, but is it like, look at their background and they've worked at a company like that? Or is it personality type? Is there anything to look for specifically there?

Annie Pearl (00:27:58):

Yeah, I think it is mostly background and the type of selling that they've done previously more so than personality type. But I think the second piece, that's important too, and I'll answer your question on that one too, which is the target buyer. So, when you transition from PLG to sales led or adding this direct sales motion, the buyer is usually just the department head. It's the head of sales, it's the head of rev ops, it's the head of recruiting and it's not a senior person in IT or the CIO. And so, selling into this audience is different than selling into IT.


And so, I think you have to be sure again that you have the right fit of sales folks with the target buyer in those early days. And so, to your question around what's that mean? You wouldn't necessarily want to bring on a bunch of sales folks who are at Oracle who are heavy in selling into CIOs in the early days because that's just not who you're the buyer's going to be. I mean, think we will graduate there eventually, but it's probably going to start from team lead to someone in IT to eventually a CIO led purchase, but that's certainly several years away. And so, making sure that the profile, the folks you're bringing on early match that target buyer in addition to match the motion around how you're going to be acquiring customers.

Lenny (00:29:15):

And to see that, is it similar? You look at the companies they worked at, it's like PLG-ish companies.

Annie Pearl (00:29:20):

Definitely. Yeah, exactly. Yep. Yep.

Lenny (00:29:23):

Okay. So, along the same lines, as a product leader working with a strong and large sales team, anything you've learned about just how to build that relationship and build a product org that works really closely and well with a sales org?

Annie Pearl (00:29:37):

The first piece that really starts with is customer empathy. And at the end of the day, seeing the sales team and the go-to-market team as this really great asset that can help you as a product manager get closer to the customer. So, I've certainly seen organizations or been in organizations where the product team doesn't necessarily want to be bothered by sales, but I sort of flip that on the head and say sales and sort of the go-to-market teams in general could be your biggest asset to helping you get your job done well.


When I was at Box, I was a product manager on the enterprise team and I spent a ton of time in the field and I don't know how I would possibly know how to have what to have built or how to build it to solve the needs of our customers if I didn't have that close relationship with the sales team and be able to lean on them because they're talking to, 10X of them were customers that I was able to ever talk to within any given week, really lean on them to be the voice of the customer to help me make the best product decisions that I could.

Lenny (00:30:35):

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I'm curious how you prioritize work that you could be doing as a product team. There are salespeople coming at you, there's issues you're probably having, there are some founders wanting to ask you for few stuffs, just like a classic product management question. But I'm curious if you found any frameworks or approaches for just deciding what to actually build of all the things you're hearing.

Annie Pearl (00:32:09):

The core challenge of being a product manager, right?

Lenny (00:32:12):

Just to add that I feel like the core job of PM is just tell people what's next, what's the next thing.

Annie Pearl (00:32:16):

That's right, and hopefully, you have a good reasoning as to why that thing, next is going to have the biggest impact, which is really where I start. I think it really starts with a clear product strategy that will dictate a few things. And I like this framework that's taken from a book called Playing to Win and it talks about how 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 sort of 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?

[NEW_PARAGRAPH]And so, what I think this framework does kind of dovetails back to what I was saying before around prioritization is it forces you to create clarity around where you're going to play and where you're not going to play. And so, this really helps the product team hone in on delivering value for a very clear set of people versus trying to build something for everyone. And so, once you've established what that strategy is or what the playing field you're going to go after, then I think you can divide up your product work and service of that strategy.


So, I'll give you an example. At Calendly, we have the sort of vision, our winning aspiration to become the best place to schedule, prepare for and follow up on your external meetings. And then, we've articulated three horizons around how we're going to get there. Now, the year one that I was here, the percentage of resources we spent on that first horizon and the second horizon was about a 70/30 split and we put 0% of our resources on horizon three. That was too far out in the future and we didn't want to make any investments there quite yet, but we knew where we were going.


In year two, it shifted. We went to a 50/50 split between horizon one and horizon two, but still, no explicit investments in Horizon three. And then, as we're entering to year three now, we've significantly scaled back the investment in horizon one, that's about 30% and then we've got 60% in horizon two and call it 10 in horizon three. So, I think just to close on the question of prioritization, I think it starts with a really clear product strategy which defines where you're going to play and how you're going to win. And then, the work and the percentage of allocation just should feed right into that product strategy and how you're doing against where you need to be in order to achieve ultimately your winning aspiration.

Lenny (00:34:38):

I don't know how much you could share here, but is there a feature that is people keep asking for it and it hasn't been built because of the strategy, the long-term vision, something that's like, "Nope, it doesn't fit. We're not going to do this."

Annie Pearl (00:34:50):

Yeah, I think the best example I can give is there's lots of small businesses and solopreneurs who would love us to have a Venmo integration. We have a PayPal integration. But our target market that we're really trying to go after as our primary persona are as I've mentioned, these sort of core ICPs within organizations. So, sales teams, recruiting teams, customer success teams. And so, it doesn't make sense within those personas to pursue something like a Venmo integration. Now, there's a lot of things we'll build for those personas that are going to help the small business, the solopreneur, the freelancer, but that specific feature is something that would be clearly deprioritized given the current strategy.

Lenny (00:35:29):

That's an awesome example. I want to get back to the growth stuff, but before I do that, we're kind of on this topic of planning and a cares and prioritization. I'd love to know just how you do planning at Calendly? How far out do you plan in detail? How far do you have roadmaps? How often do you plan? Anything you can share there?

Annie Pearl (00:35:45):

This starts again, I sound like a broken record, but with this really clear strategy around where we're going over the next couple of years and then we take that and we break that down into what are the most important things we need to do as a company this year in order to be able to make the right progress against that strategy. So, we have the company level OKRs and I mentioned that we have about three of those this year. And then, those KRs within the company, OKRs are measured annually, but we have milestones across a quarterly basis so we can measure progress more frequently than obviously on the annual or semi-annual basis.


So, I think that's kind of at the high level. And then, obviously our product roadmaps are going to be in support of those key results that we needed to deliver to the business over the course of the year, but then broken down on a quarterly basis.


I think one thing I'll just touch on real fast on is estimations and dates. Something we've done over the last year is really kind of moved to a model of talking about dates and promising and committing to dates that are within our control. And so, if you think about the product development life cycle, we can commit to a discovery effort of doing research around a certain problem space and we can have a general sense of when we know that effort's going to conclude. We don't know if we're going to actually end up going, and based on the results whether we're going to actually move forward with investing in that area, but that's a body of work we can commit to.


From there, we then move into, "Okay, if this is something a problem space we want to go after, we're going to go work on a couple different solutions and we're going to go do some user testing and we're going to land on a solution," and that's another sort of phase we can commit to. Then, once we actually have that completed and we actually know not just the problem but the solution, we can do estimation planning and actually have a date for delivery from an engineering perspective. And so, we've gotten a lot better at making the commitments around the work that's right in front of us versus making a commitment around a project six months out when we haven't even done enough discovery, enough design and ideation to have a real clear understanding of estimation.

Lenny (00:37:43):

That is really cool. Do you have terms for these phases, like these phases you have to get through these kinds of gates? Yeah, how do you describe that?

Annie Pearl (00:37:50):

Yeah, so the first phase we just call generally discovery. The second phase, we call solutioning. The third phase, build. And then, the fourth phase is launch, measure and iterate.

Lenny (00:37:50):


Annie Pearl (00:38:01):

And then, we've designed the product development lifecycle around that framework.

Lenny (00:38:04):

So, discovery for example, is that a roadmap item for a quarter and that's like what you've committed to? And if that goes well, the next quarter has the next step.

Annie Pearl (00:38:12):

Yeah, exactly. You got it.

Lenny (00:38:14):

Sweet. Okay. In terms of the strategy artifacts, how does that look or do you have a Google Doc with a template that you all use? What does that look like? What's interesting about people not working at a company or working at just one company is they only have, strategy documents are really hard to see and see examples of. So, I'm always curious what these looks like. So, whatever you can share about what they look like and where you put them and how long and that kind of thing.

Annie Pearl (00:38:40):

We have a couple of different layers of this. I think the first is this high-level three-year strategy and this is actually called at the company level. So, if the doc, it also has slides that have been presented many times to the company when we're in the process of making sure that, that is part of new hire orientation so that everyone should understand where are we going over the next three years and then therefore how does this year's objectives fit into that. So, I think that's at that level.


And then, from there, we've got our product team OKRs. These generally start by docs and we write them in docs. So, they usually get translated into slides at some point for presentation purposes to the company and those are stored centrally in a location and then you get down to the feature level or the project level. And we have different kind of templates for the teams to use based on the type of work that they're going to be doing. And we're a pretty heavy Confluence culture, so we tend to use Confluence as one of the tools for housing and storing information around the work that's being done.

Lenny (00:39:39):

Cool. So, maybe on that topic, what else is in the stack of Calendly product team tools?

Annie Pearl (00:39:44):

We talked about roadmap planning, some combination of starts with docs, there's mural boards involved. Usually, it ends in slides. Then actually roadmap tracking, we use Aha and we use Airtable collaboration/communication. We use Slack, we use Loom, bug management, we use Jira. I'm trying to think of, is there any other?

Lenny (00:39:44):

Confluence, you mentioned.

Annie Pearl (00:40:05):

Confluence. Yep. Confluence is what we use quite a bit. Pando, we use quite a bit of Pando to help educate users within the product when we're launching new features. Yeah, I think that's the main stack.

Lenny (00:40:16):

And docs is Google Docs and slides is Google Slides.

Annie Pearl (00:40:19):

You got it. Yep.

Lenny (00:40:20):


Annie Pearl (00:40:21):

That's right.

Lenny (00:40:21):

Okay. I'm going to bounce around and go back to growth questions and then I have a couple more product team questions. How did Calendly get their first thousand users?

Annie Pearl (00:40:30):

A great question and I had to fact check it with my CEO earlier this morning, but there's actually a few really interesting things about this story and a few things that Tope did in the early days to get 2,000 users. So, for those who aren't familiar Tope, our CEO and founder started his career in sales and he spent lots of years in sales. And so, he was very used to the challenges of trying to organize external meetings with prospective customers. So, he knew the problem space really, really well. And he had evaluated all the scheduling solutions that were on the market and came to conclusion that there really weren't any great products out there and especially there weren't any great products for the recipient of the actual booking service. And so, I think he saw this as an opportunity for disruption. So, he raided his 401k, he took out all his savings. He didn't make raise any money.

Lenny (00:41:23):

That's a lot of penalties, taking out money at that point.

Annie Pearl (00:41:23):

Sort of. That's a very good point. I've never asked him about that. And he hired an outside development firm actually in out of the Ukraine to build the first version of Calendly. So, that's the background on Calendly. Why it's important is that the first 10 users were actually customer success agents at a company in the education space that contracted with the same firm that Tope was using to build Calendly. So, he really found his first set of users through the firm that he was using to build the product.


And then, those CSMs or customer success managers were actually using Calendly to schedule calls with parents in K through 12 education. And so, then those parents started using Calendly for their own parent-teacher conference scheduling. And then from there, the school started using it and then all the parents within the school started using it for lots of other use cases and it grew organically from there. So that was one piece.


I think the other piece that's really important is that he started off by just having a free tier. The entire product was free. Some of this came from honestly not being able to actually build the billing infrastructure that would be required to actually charge. So, it came a little bit out of necessity, but it was also free. So not only was it a better product than the alternatives out there, but it was also free. So, the combination of the viral loop and coming in through getting those first 10 users as part of the firm he was using and then the free aspect or I think what led to the first 2,000, and then 10,000, and millions of users from there.

Lenny (00:42:52):

That is crazy. I have never heard a story like that where the team that is building your product ends up being the source of initial growth.

Annie Pearl (00:42:58):

I know, pretty crazy.

Lenny (00:43:00):

Oh my God. So many nice things happening in this history of Calendly.

Annie Pearl (00:43:03):

I know.

Lenny (00:43:03):

And wow, in Ukraine. So, I'm actually from Ukraine.

Annie Pearl (00:43:08):

Oh nice. That's awesome.

Lenny (00:43:08):

That's pretty cool.

Annie Pearl (00:43:09):

Yeah, they're great. [inaudible 00:43:11].

Lenny (00:43:11):

Yeah, and it's also interesting that it's rare that you hear a successful business starts with contractor engineers. I think OICs are like, "Do not do that." So that's a cool counter example of it can actually work out, especially if they're your first users and spread it to others.

Annie Pearl (00:43:27):

And we still work with them. They're fantastic and they have incredible engineers, so they're still part of our culture, which is great.

Lenny (00:43:32):

So, Calendly got big in Ukraine, it sounds like initially.

Annie Pearl (00:43:35):

There you go. There you go.

Lenny (00:43:37):

What's something that would surprise people in terms of how Calendly grows today or grew through its history?

Annie Pearl (00:43:43):

Most people probably think about Calendly as the scheduling link and really for individual users to reduce the back and forth of email and scheduling. So, they think of that one-on-one use case and I think people would be surprised to learn that our team's business, so multiple users in an organization who want to collaboratively schedule together is growing much faster than our solo user business. And that's really where the future of where we think growth will come from is supporting these teams of users who are in externally facing roles and selling into departments and supporting multi-departmental deployments of Calendly across an entire organization.

[NEW_PARAGRAPH]So, I think it's still really well known as this solo user tool to eliminate the back and forth of email, but the growth of what we're seeing and where we think it's going to go is actually more teams of users and departments of users and then multiple departments in an organization.

Lenny (00:44:32):

It's interesting when you hear the story of Calendly that just has so many good things happening, basically for free, it's just grows so well. I think people don't realize you eventually will, that'll slow down, it'll taper off eventually. You'll need to drive growth very actively in these new ways that you're describing. And I think people don't often realize that they just wanted to find something that was viral and then things are going to go great, but it tapers off.

Annie Pearl (00:44:54):

Yeah. I mean, there's only so many people who, solo users who are going to pull out a credit card. And I think once you also get to hundreds of millions of dollars of revenue scale, just the law of large numbers, it means that growth will slow. And so, you have to figure out where's that next growth curve going to come from. I think the beauty of Calendly is that while we certainly have built features and functionality to support teams and departments, we got pulled there. It wasn't one of those things where we sort of said, "We need to find our next growth lever. Let's go build X." Our customers really pulled us there by the way that they were using the product.


And so again, a very fortunate position to be in, but when you can see in the data and see how customers are using it, that they want to be working on scheduling with their teams, that was our early sign, that's where the business was going to go in the future.

Lenny (00:45:46):

I don't think I mentioned this, I'm paying user of Calendly. It's what I use for booking these podcast episodes.

Annie Pearl (00:45:50):

All right.

Lenny (00:45:50):

You got me. I think I started when it was totally free and I was like, "How will they ever make money?" This is too much power.

Annie Pearl (00:45:56):

And then, now, you learned that it was free almost by accident.

Lenny (00:46:02):

Yep. I was like, "Yeah, please take my money. This makes my life easier." What are some fun or unique traditions and cultural kind of components of the Calendly product team?

Annie Pearl (00:46:12):

A couple of fun ones I thought we could talk about. One, we have a meeting called OPA, which stands for opportunity/problem, assessment. And so, what this is, it's a meeting where basically PMs, I don't even go to it's a meeting for PMs to really debate and discuss with each other and spar around either areas and problems that they want to go investigate or after they've gotten data back or research back from evaluating an opportunity, deciding whether we actually want to move forward and go try to develop a solution. So, it's really in the product development lifecycle of letting product managers really get into a room with each other on a frequent basis and just think through things, debate, discuss. And I know that they all get a lot of value out of that.

Lenny (00:46:59):

It reminds me of something just like a bad version of that. I had a friend who was a PM at Zynga and he said there's a meeting where PMs present their plans to all the other PM. It was like you're in a shark tank where everyone's coming to destroy you. They just point out all the problems. That's all it ever is in this.

Annie Pearl (00:47:15):

I would say on this one, it's the opposite where I feel like everyone really needs the meeting. They're like, "Ugh, I really need to take this to OPA because I need to, I'm working through these problems and I really want to bounce it off of other people." So, I could imagine a world where it would be that. Actually, part of the reason I don't go to the meeting is that I really want everyone to be able to be open and transparent and provide feedback and not feel like there's any judgment from me or any needing to act a certain way because I'm in the room. So, that's sort of why I intentionally don't go.


Another fun one we do is something we call competitive work gaming. So, on some sort of time interval, sometimes it's been quarterly, we'll have assigned people into groups for the quarter to own a competitor. And their job is to essentially spend a lot of time immersing themselves into the product of the competitor, really trying to think through the lens of, do a SWAT analysis, really try to think through the lens of where's this competitor going and how Calendly only think about that and as it relates to our strategy.

[NEW_PARAGRAPH]And so, we spent a quarter doing that and then we have the competitive war gaming day where every team comes and presents and there's prizes and it's a lot of fun, but it's a really great way to stay on top of what's happening across the market without requiring every product manager designer to be deep in the weeds, there are a lot of different competitors. We can bring all of that knowledge together through what we call competitive work gaming.

Lenny (00:48:34):

That is cool. It's really impressive how you do these exercises and they seem really positive and friendly and constructive. It sounds like there is a pretty unique culture at Calendly. I'm curious if there's anything else that's core to the values or the way that you think about the principles of building product at Calendly.

Annie Pearl (00:48:51):

What I touched on earlier is really core to how we build product, which is honing in on this target user and honing in on our target market. I do think it's quite rare. I think in most organizations that I've seen, I think there's a desire to do that. But I think, again, when it push comes to shove, it's really hard for executives to make decisions that say no to things. One of Calendly's actually core principles is focus wisely. It's pretty deeply embedded into our culture. And so, I think one of the reasons that I've been successful in being able to create the clarity around who the target personas are is because I think it's embedded into the culture of Calendly to focus wisely.


So, I don't know that it'll work in every organization. I think many organizations really struggle to say no, and they're always adding more onto the plate versus taking off. But I do think from an ethos perspective, there is something around focusing and the ability to focus to therefore deliver the highest quality of product that you can to your target customers. That is unique and I think it starts with some of the broader cultural paradigms that exist at the company and then we've now embedded that into the way we think about how we build product.

Lenny (00:49:59):

Is there anything else you do to instill that? It sounds like it's a core value. Do you put posters around the office? So how else do you keep people focused?

Annie Pearl (00:50:06):

We're a fully remote company. So, now you've got my brain going on. Are there some sort of virtual sticky notes that you could get people to put onto their laptops to remind them?

Lenny (00:50:15):

Backgrounds to show us [inaudible 00:50:16].

Annie Pearl (00:50:15):

Yeah, exactly. Yeah, it's embedded into a lot of the documentation. So, it's embedded into the templates that I talked about in terms of, everything from sort of the way we structure that OPA, document that folks are going to be working on and debating too when they go to create the actual sort of PRD. When teams come in to present as part of our product reviews, we have a template that keeps reinforcing who's the target customer, who's the target user within that customer base, what are their needs and then how are we going to solve their needs better than any alternative that there is on the market. So, I think there's lots of different reinforcing mechanisms to that focus.

Lenny (00:50:57):

I feel like sometimes things like that come from a big problem the company had and then you index weigh the other side, focus, here's the four people we all build for. It becomes instilled in the culture.

Annie Pearl (00:51:08):

And I think you're right. I mean, because Calendly started as such a horizontal product, which was amazing because that's how it grew so virally and so it had the entry, the wedge into scheduling and how our first horizon and becoming the best horizontal scheduling automation platform was because we had that horizontal focus. And so, it was a blessing. But as we think about transitioning to horizon two, which is really about deepening our support for these teams and departmental users as well as verticals, that's I think the inflection point where we said, in order to shift us from horizon one to horizon two, we need to be making some real trade off decisions and we need to create this focus so that we can actually allow teams to go do that.


So, I think it's a really good point. We sort of had to create clarity around focus because we were trying to make a shift from broad horizontal platform serving lots of users to a deeper investment into specific users and specific teams of users within departments.

Lenny (00:52:07):

Before Calendly, you were at Box. Before that, you were at Glassdoor. I'm going to ask two different questions. You could pick which direction you want to go. What would you say are the biggest differences culturally between these three? If you had to bucket, here's how I'd describe Glassdoor, Box, Calendly. Or what did you take from those two places that you bring with you to Calendly and future opportunities?

Annie Pearl (00:52:27):

I love this question. So, they're all different, which is why I just feel so fortunate to have had experiences that were all quite different. So, starting with Box, maybe I'll take your second question. Box, when I joined, we were in the process of moving up market and trying to capture as much enterprise market share as possible, and I was on the enterprise product management team. So, I spent a lot of time, as I mentioned earlier, talking to customers. And in my first year in particular trying to ramp on the business. And I'd say my biggest learning during that time was around how to ask the right questions to really understand the why behind what a customer was asking for and then figuring out how to build a solution to their problem that would also meet the needs of a broader swath of customers.


It became very clear early to me if I would just go build what customer A wanted and what customer B wanted and the customer C wanted, not only would that be wasted effort to do it three times, but more importantly, what they wanted me to go build was going to have a negative impact on the end user experience. And preserving that end user experience was so critical. So, learning how to ask the right questions to understand the actual problem and then build the solution that's going to be most scalable to that problem set across lots of customers was probably my biggest learning from Box.


Moving to Glassdoor, totally different business model. Glassdoor is actually really more of a consumer business and 60 million unique users go to Glassdoor every month and it's a marketplace between job seekers and employers and it's highly, highly dependent on the consumer engagement, growing traffic, getting that traffic to come and engage and apply to jobs. And so, during my time as CPO there, I was responsible now for both sides of that marketplace, the consumer business and the B2B. And so, I learned all about how do you build PR consumer products, how do you think about optimization of a funnel? How do you think about building up a growth team and growth as a discipline? How do you use data and AB testing to make decisions?


So, I think that kind of consumer mentality and how you approach product, I then have brought with me to Calendly, which is really a blend of both, right? Calendly is first, as we've talked about a PLG business and it looks a lot more like a consumer business like Glassdoor. And then, it's got this direct selling business that looks a lot more like Box's enterprise business. So, I think I've been able to take kind of lessons learned from both Box and Glassdoor and apply them together to Calendly.

Lenny (00:54:43):

What a cool set of experiences. I'm trying to imagine you using all three in the same day. Sending a Calendly, storing your files in a Box and looking at reviews...

Annie Pearl (00:54:53):

And recruiting.

Lenny (00:54:54):

And recruiting. Yeah, yeah. Not looking for anything new. Okay. Final question. You are part of something called the Skip community, which I believe Nikhyl and a few people run. And so, I'd love to just hear a little bit about that and maybe how folks can join if they might be a fit.

Annie Pearl (00:55:08):

Yeah, as you mentioned about two years ago, Nikhyl, who was the former CPO of Credit Karma and is now a VP of product at Meta, got a small group of CPOs together who were all going through similar phases of companies' growth, late stage growth companies, and we all were facing the same challenges in our roles. And he formalized this community as a way to help us gather advice from one another, talk through how to manage challenges we're facing and just make us more successful in the roles. And we always joke, we're like the support group.


We meet on Sundays and it has been incredibly valuable as I've sort of gone through the last couple of years in my role at Calendly. Since then, we've grown the group to about 23 heads of products and CPOs and expanded the charter a bit, which I think is interesting to help product leaders not just be successful in their current role, but also how to think about setting them up for success in the role after this.


And so, we're experimenting with a couple of different interesting ways to help product leaders grow. One of them is we're actually partnering with some companies right now to experiment with how can we help them as they're looking to make their first head of product hire or their first C O hire really hone in on what they're looking for and partnering with the talent partners we know to really help try to increase the success that they find the right candidates. That's something interesting we're doing.


We also recently launched a podcast covering some topics like, how do you manage the next job search, how do you avoid burnout, breaking down things like equity, and other kind of timely topics. And then also, we just have an active Discord server where we've got all sorts of channels from topics, how to manage the CEO/CPO partnership, compensation, even sharing planning, even sharing some advising opportunities or other CPO roles that kind of come across our radar.


So, it's been a really, really cool kind of experiment to see how the power of the community. And I know Lenny, you do a ton of stuff around community, how that has helped all of us. I think it's just more effective in our roles and feel like we have a group of people who are behind us supporting us during what is a very hard role.

Lenny (00:57:11):

I love this. I imagine when people look at a CPO, they imagine they just know everything already. They have a bunch of friends in the same role, but I think in reality, it's a lonely role a lot of times. And so, I could see the power of something like this just to help people understand who'd be a good fit for this, how do they go find it and yeah, it's like the [inaudible 00:57:33].

Annie Pearl (00:57:33):

The best thing to do is just follow the Skip community on LinkedIn. And then, we're targeting head of products, call it series B, C and beyond, up to late stage growth companies and up to CPOs. So, I'd say start by following the Skip community and if you see folks in there who are in the group, reach out to them to get a sense of what it's like and what it would be like to join.

Lenny (00:57:57):

And then, it sounds like if you're a company hiring a CPO, maybe reach out too.

Annie Pearl (00:58:00):

Yeah, that'd be great. That'd be great. Yeah.

Lenny (00:58:03):

Okay. And they do that by going to LinkedIn also and looking for the Skip community?

Annie Pearl (00:58:06):

Yeah, that'd be great.

Lenny (00:58:07):

Okay, cool. We'll put all the links in the show notes as well. Well, with that, we've reached our very exciting lightning round. I've got six questions for you. Are you ready?

Annie Pearl (00:58:15):

Let's do it.

Lenny (00:58:17):

What are two or three books that you recommend most to other people?

Annie Pearl (00:58:20):

Playing to Win, so, I reference that one earlier, Good to Great, and Hooked.

Lenny (00:58:25):

Awesome. What's a favorite other podcast that you enjoy other than maybe this podcast?

Annie Pearl (00:58:30):

I think I got introduced to you by Harry from the 20VC, I think. But if not, either way, I'll cross promote his podcast, which is a great one.

Lenny (00:58:39):

Yeah, Harry's responsible for this podcast. I was on his podcast and he's like, "Lenny, you should be [inaudible 00:58:43]".

Annie Pearl (00:58:43):

You got to do it.

Lenny (00:58:46):

He's the godfather of this podcast.

Annie Pearl (00:58:48):

He is. That's great.

Lenny (00:58:49):

What's a favorite recent movie or TV show? And you cannot say White Lotus.

Annie Pearl (00:58:53):

I have two young kids. So, whether I like it or not, Sing 2. It's a great movie, especially if you have young children.

Lenny (00:59:00):

Sing 2. So, it's like the second of Sing?

Annie Pearl (00:59:03):

It is. It is. Distinct from Sing 1. Sing 2 is better.

Lenny (00:59:07):

It's better. Okay, cool. I haven't seen it.

Annie Pearl (00:59:10):

I would hope you haven't.

Lenny (00:59:11):

Okay, cool. Favorite interview question that you like to ask people you interview.

Annie Pearl (00:59:15):

Talk me through your biggest product flop. What happened and what did you do about it?

Lenny (00:59:21):

What do you look for in an answer? What's a sign of something good in their answer?

Annie Pearl (00:59:24):

People being brutally honest around how bad it was and why it failed. The rest of the interview, they're trying to tell you all the wonderful things they did and all the accomplishments they had. And so, I think the rawer the answer in terms of how bad it was and why, the better.

Lenny (00:59:38):

Awesome. Next question. I think, you might have answered, what are top five SaaS products you use day-to-day, either at work or home, whatever?

Annie Pearl (00:59:46):

Slack, Miro, Loom, Pendo, and Confluence.

Lenny (00:59:51):

Awesome. And these are actually, unlike other people's answers, so that's really interesting. Kind of a unique stack you got there.

Annie Pearl (00:59:57):

I love it.

Lenny (00:59:58):

Final question. What's your best Calendly Pro tip?

Annie Pearl (01:00:01):

Yeah, so we just launched a new feature that I'm loving personally called Customized Once and Share. So, this really allows you to make changes on the fly to an event type and tweak things like title or duration or override a date based on the person you're actually sending it to without having to go create a brand new event type just to make one small change based on the recipient. So, it's that one-off use case where you need to make a little bit of a change on the fly depending on who you're sending it to, but you don't want to go through the effort of creating a brand-new event type. So, I'm loving it and you should check it out.

Lenny (01:00:34):

That is awesome. I need that. I find that I need to block dates out and change times and I just like go do that on my calendar, in my Calendly.

Annie Pearl (01:00:42):

There you go there.

Lenny (01:00:43):

All right. Annie, this was amazing. We learned a ton about Calendly growth product building. Two final questions. Where can people find you online if they want to learn more and reach out, maybe ask some questions. And two, how can listeners be useful to you?

Annie Pearl (01:00:56):

Finding me, best place online is LinkedIn. And then, in terms of being helpful to me, one we're hiring at Calendly. So, explore open roles on the product team at Calendly if you're interested. Share any feedback for me on this episode@a.pearl@calendly.com. And then, as we talked about, would love to have you follow the Skip community on LinkedIn as well.

Lenny (01:01:15):

Awesome. We'll have all those links in the show notes. Annie, thank you again for being here.

Annie Pearl (01:01:20):

Thank you so much, Lenny.

Lenny (01:01:22):

Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.