Lenny's PodcastBehind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)
EVERY SPOKEN WORD
135 min read · 27,359 words- 0:00 – 3:50
Annie’s background
- APAnnie Pearl
Strategy is really just an integrated set of choices that outline how you're going to win in whatever marketplace you choose, right? 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? You know, what are the markets you're going to go after? What are the segments of those markets? What are the personas in those segments of those markets? And then how are you going to win with that target audience?
- LRLenny Rachitsky
(intro music plays) 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 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 after 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. For example, with Miro, you can plan out next quarter's entire product strategy. You can start by brainstorming, using sticky notes, live reactions, a voting tool, even an estimation app to scope out your team's sprints. Then your whole distributed team can come together around wireframes, draw ideas with the pen tool, and then put full mocks right into the Miro board. And with one of Miro's ready-made templates, you can go from discovery and research, to product roadmaps, to customer journey flows, to final mocks, all in Miro. Head on over to miro.com/lenny to leave your suggestions. That's m-i-r-o dot com slash lenny. This episode is brought to you by Coda. You've heard me talk about how Coda is the doc that brings it all together, and how it can help your team run smoother and be more efficient. I know this firsthand, because Coda does that for me. I use Coda every day to wrangle my newsletter content calendar, my interview notes for podcasts, and to coordinate my sponsors. More recently, I actually wrote a whole post on how Coda's product team operates, and within that post they shared a dozen templates that they use internally to run their product team, including managing the roadmap, their OKR process, getting internal feedback, and essentially their whole product development process is done within Coda. If your team's work is spread out across different documents and spreadsheets and a stack of workflow tools, that's why you need Coda. Coda puts data in one centralized location, regardless of format, eliminating roadblocks that can slow your team down. Coda allows your team to operate on the same information and collaborate in one place. Take advantage of this special limited time offer just for startups. Sign up today at coda.io/lenny and get $1,000 startup credit on your first statement. That's C-O-D-A dot I-O slash Lenny to sign up, and get a startup credit of $1,000. Coda.io/lenny.
- 3:50 – 6:04
How to send a Calendly invite without feeling awkward
- LRLenny Rachitsky
Annie, welcome to the podcast.
- APAnnie Pearl
Thanks for having me, Lenny. Super excited to be here.
- LRLenny Rachitsky
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.
- APAnnie Pearl
Me as well.
- LRLenny Rachitsky
I've got a Calendly question to kick things off. It feels like with Calendly, one of the most awkward elements of it is that I have to, like, put the burden on someone else to book a Calendly. So I'm sending a link and then... 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? (laughs)
- APAnnie Pearl
All right. Well, I love this question to kind of kick us off. We actually have a whole blog post about this, if you're, uh, curious to learn more, but...
- LRLenny Rachitsky
Okay. Hopefuly so.
- APAnnie Pearl
(laughs) I think that at a, 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, right? So instead of just sending the link, I usually start the email with something like, you know, "Looking forward to connecting. Feel free to share some times you're available." Or if easier, "You can choose, you know, 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, you know, a little bit of a subtle way to, to let them take the lead if they want. The second piece I would recommend too is once you've kind of opened that door, you can kind of 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, you know, get taken to Calendly. So opening the door and then, you know, adding times to email are two things that I do to, to really make sure that it's not awkward and it doesn't put the burden on the other person.
- LRLenny Rachitsky
That is awesome advice. That first one is kind of what I ended up doing actually, that's really interesting, where you don't send the link immediately. You first-
- APAnnie Pearl
Yeah.
- LRLenny Rachitsky
... just ask, "Hey, send me your Calendly." And I actually act- always say, "Send me your Calendly." Like, I don't even... I assume that's what they're using. It's kind of funny.
- APAnnie Pearl
(laughs) Right.
- LRLenny Rachitsky
I'm not even like... I don't know what else is out there.
- APAnnie Pearl
That's good. That's what we like to hear.
- LRLenny Rachitsky
Yeah, absolutely. It's like its own word now. Okay, that was awesome. Oh, look at this, already actionable advice for anyone listening.
- APAnnie Pearl
Sweet.
- 6:04 – 9:53
How to transition to product work from a non-technical career
- APAnnie Pearl
- LRLenny Rachitsky
Transitioning a little bit to product, the main focus of our 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, someone without a technical background. So what advice do you give people for when they ask you how to transition into a product role?
- APAnnie Pearl
I got, you know, what I'll call lucky, which is I kind of stumbled into product management after law school. I joined the founding team of a startup and, you know, ended up doing product management there. But when I think about folks who are looking to get into product management, I think there's really two paths. I think one is kind of more formal in nature, right? There's associate product manager programs out there. Many, you know, 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, uh, a, an APM program to help grow our bench of more junior PMs. 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 is just formal APM programs. I think another kind of more, quote-unquote, "formal" way to get into PM is really by just, you know, directly applying to a junior PM role where there's no expectation of, of any sort of experience. I've usually seen this work best when you're kind of already working somewhere in some sort of product adjacency. You know, maybe you're in customer support, implementation or maybe you're a sales engineer, but you can kind of look at the internal, you know, job board and find junior PM roles that are posted and, and that's, uh, 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 kind of seek out opportunities to kind of shadow or partner closely with, with a product manager and maybe even offer to take on some work. So some of the kind of best PMs that I've brought over to product from kind of other functions, they really start by expressing interest in product and then like start pro- partnering closely with the product manager and maybe even doing a little bit of product work before they make that transition. And one kind of 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, you know, becoming a SME, uh, y- allows you to really get more involved and embedded into the product team. So that's, that's one suggestion. And then maybe last one is just, you know, going the path I did, which is joining an early stage startup. Uh, 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, you know, try product management if you end up kind of joining an early stage company.
- LRLenny Rachitsky
So the four... Maybe it was four, maybe it was more paths that you described.
- APAnnie Pearl
Mm-hmm.
- LRLenny Rachitsky
Join APM program. What was the second one again?
- APAnnie Pearl
Internal job board, apply to it while, when you're in the company.
- LRLenny Rachitsky
As just like a junior PM. Two is find someone that kind of like mentors you and helps you start doing the role. And is that internal kind of tra- is that the internal transfer route?
- APAnnie Pearl
Yeah, exactly. And then-
- LRLenny Rachitsky
Cool.
- APAnnie Pearl
... uh, s- another sort of flavor of that is, you know, sometimes companies will have these sort of SME programs.
- LRLenny Rachitsky
What is a SME program?
- APAnnie Pearl
A subject matter expert.
- LRLenny Rachitsky
Oh.
- APAnnie Pearl
So, you know, you'll say, "Hey, I want to make sure we have a subject matter expert in our CS team on this area of the product," and they'll partner really closely with, you know, the product manager and designer within that area.
- LRLenny Rachitsky
Got it. And then the fourth bucket is join a startup, start doing PM work, and then you end up being a PM.
- APAnnie Pearl
You got it.
- LRLenny Rachitsky
Which of those four do you find most common, and would you push people in one direction or another?
- APAnnie Pearl
Yeah. You know, I, I've brought a lot of folks over internally through the, through the path of someone's really interested in product, they expressed 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, you know, 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, bring the most folks over in my role in terms of being on the product leadership side.
- 9:53 – 10:52
APM programs
- APAnnie Pearl
- LRLenny Rachitsky
On the APM program route, are there any APM programs you recommend? 'Cause you know, 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, I don't know if you have a list, but just like what comes to mind as like APM programs to go pursue?
- APAnnie Pearl
You know, the, the sort of, the, the folks who started it all was, was Google, right? With the Google APM program, and you know, Meta obviously has a pretty strong, a robust APM program. But as I mentioned around Box, I think, you know, those are obviously very, very competitive and most people want to get into them. It, you know, it may be better to try and find a company like a 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 went to gl- go to glassdoor.com... I used to work at Glassdoor, so I had to, you know, throw that in there. Uh, you could search for associate product manager and I think you'll find a whole host of, of open roles that you might be able to apply to.
- LRLenny Rachitsky
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 like title section?
- APAnnie Pearl
Yep. You can just, uh, associate product manager and you'll see-
- LRLenny Rachitsky
Mm-hmm.
- APAnnie Pearl
... all the open jobs out there and then, uh, go apply to them.
- LRLenny Rachitsky
That's cool. Okay. Good tip.
- 10:52 – 13:26
The characteristics of internal-transfer PMs
- LRLenny Rachitsky
What I find, and I... you mentioned this, like the best if you have the option is to internal transfer, right? If you're just looking at another function, you find someone that can help you move into the role.
- APAnnie Pearl
Yep. You have the relationships, you, you know, you can show, you can show your work really well. The only other thing I would say is, you know, when I think about folks who have successfully transferred over, I think they tend to have a couple characteristics, right? They're usually very curious. They tend to be really passionate about the product and kind of solving customer problems. And sometimes they've even like tinkered with a side project as a way to kind of 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, in the product itself and solving customer problems are also great ways to get noticed and, uh, increase your chances.
- LRLenny Rachitsky
Why do you think it is that not more companies have an APM program feels like such a win for so many people? Why is it just so rare?
- APAnnie Pearl
Yeah. I think when we built this at Box, so kind of drawing on that experience, it was a lot of work, right? You want to... If you're gonna 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. You know, with 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, uh, for us it took a lot of, you know, it took a lot of work, right? 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 tr- 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, 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 gonna help make sure everyone who comes through it has a chance at really learning, growing, and ultimately being successful.
- LRLenny Rachitsky
That's the same thing we found at Airbnb. There's a PM...... that was so excited to, like, make the APN program and just, 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 what do you, when do you upgrade to a regular PM, and-
- APAnnie Pearl
Exactly.
- LRLenny Rachitsky
... how do you interview, and, you know.
- APAnnie Pearl
And are we doing, you know, is this really an APN program for internal folks? Is this external? You know, are we gonna be really trying to promote this? Uh, 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.
- LRLenny Rachitsky
Yeah. Maybe a last point we should probably, I imagine you agree with, is generally just hard to get into product management. That's like the default. There's just, like, not that many roles at companies versus the engineers or some other-
- APAnnie Pearl
That's right.
- LRLenny Rachitsky
... functions. So I think that's just like, there are not that many roles, it's like a difficult role to break into.
- APAnnie Pearl
That's right.
- LRLenny Rachitsky
But these are the ways you can do it if you actually want to.
- APAnnie Pearl
That's right. Yep.
- 13:26 – 14:57
How Calendly structures product teams
- APAnnie Pearl
- LRLenny Rachitsky
Okay. So I wanna transition a little bit to talking about Calendly.
- APAnnie Pearl
Sure.
- LRLenny Rachitsky
There's kind of 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, like how many product managers are there, and yeah, how many PMs are there? How many people total roughly?
- APAnnie Pearl
Yeah.
- LRLenny Rachitsky
Just give us a little bit of information.
- APAnnie Pearl
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 of about, there were about 15 product managers and designers when I joined, again, about two years ago, and I think we're around 60, uh, this year.
- LRLenny Rachitsky
Wow. So 60 product managers.
- APAnnie Pearl
Product managers, designers, and a research team. Yeah.
- LRLenny Rachitsky
Got it. What about just like PMs?
- APAnnie Pearl
PMs, probably my guess is 20-
- LRLenny Rachitsky
Cool.
- APAnnie Pearl
... 20-ish. Yeah.
- LRLenny Rachitsky
Cool. And then can you talk about how the product team is structured roughly?
- APAnnie Pearl
Yeah.
- LRLenny Rachitsky
Like if you think about a tree, rich art tree.
- APAnnie Pearl
Yep. So we have, 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 a 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.
- LRLenny Rachitsky
Got it. So you manage the design team and engineering team, you said?
- APAnnie Pearl
Not engineering. Design, product, and research. Yeah.
- LRLenny Rachitsky
Got it.
- 14:57 – 16:58
Why Annie hired a Head of Design
- LRLenny Rachitsky
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?
- APAnnie Pearl
Yeah. So when I was at Glassdoor in the CPO role, uh, I had the opportunity to, um, lead design for the first time. So coming into Calendly, I'd, I'd led both product and design as well as research. And so I think, you know, it kind of made sense given I'd already done it once to sort of keep that structure coming into Calendly. I think at the end of the day, the, the real benefit of, of the structure is really to say 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, you know, product managers who are really prioritizing the problems we're gonna go after, and we've got designers who are really trying to think about how do we, you know, 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 can work where you have product and design reporting into, you know, sort of different leaders that ultimately report into the CEO. But when you, you know, get to this level of scale from just a pure, uh, people management but also just the scale of the business, you know, you often see this consolidation where product and design, uh, start to roll into one leader. And, you know, at least if in, in my experience, I think it can help ensure that all the, the different pieces of work are kind of integrated well together and ultimately deliver, you know, better experience for customers.
- LRLenny Rachitsky
So it sounds like before you joined, it wasn't like that. And if that's true, is there like something that improved with that shift?
- APAnnie Pearl
So th- the structure was there that way. At the time, we didn't have a head of design, so we had a, you know, a lot of really great individual contributors and who, who had been, many of whom had been with the company for, 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, you know, head of design is, is sort of up here partnering with the different heads of products across the product management organization as well.
- 16:58 – 19:07
How Calendly structures product teams
- APAnnie Pearl
- LRLenny Rachitsky
What about in terms of the structure, whatever you can share, like one level below, like how do you structure teams? Is it around outcomes? Is it around features of the product? Is it around type of persona?
- APAnnie Pearl
Yeah.
- LRLenny Rachitsky
How do you think about that?
- APAnnie Pearl
Yeah. Yeah. So we have, you know, a core team who's really responsible for the core, you know, end-to-end user experience, and, you know, in many ways, they're both building, you know, doing feature development and then they're also doing growth work, right? So they're, 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, to really help our core end user persona, and then, you know, growth work to think about the, the PLG funnel, right? Everything from acquisition, activation, conversion, and retention. So that's one group. And then second group is our kind of quote unquote "enterprise" group, uh, and they're really thinking about two different personas. One is the sort of IT admin, uh, right? The, the sort of person who needs to make sure that Calendly is, uh, secure and that they have all the reporting mechanisms to be able to manage their account and all the tools to, you know, manage users and groups at scale. And the second piece of that is also kind of departmental leaders, right? So is Calendly selling into or being used by a sales organization? The head of sales is not the IT admin, but they are a kind of, you know, a teams admin who needs to manage the, their organization within Calendly. So the enterprise group really thinks both about the admin, but also sort of the departments, uh, and how do we better serve departments? And then lastly, we have a platform team who's really thinking about, you know, how do we embed Calendly into the business processes of the organizations that we support and, and that we, you know, provide our product into. And so that's everything from, you know, partnerships and integrations to our APIs.
- LRLenny Rachitsky
Interesting. So it's kind of like problem-focused/persona-focused, like who are you trying to sell it to?
- APAnnie Pearl
Hmm. That's right, that's right. Yeah, t- trying to sell it to and then sort of the persona of- of who's gonna be using the functionality. And then, you know, really having those teams hone and own those personas, uh, as they're, you know, developing functionality within the product.
- 19:07 – 21:02
OKRs at Calendly
- APAnnie Pearl
- LRLenny Rachitsky
What's your take on OKRs? Do you all use OKRs in some form?
- APAnnie Pearl
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, uh, level OKRs, but then, you know, there's some additional things that we'll being doing at the department level, for example, that aren't gonna show up at the company level. So yeah, we use them both at the company as well as, uh, on the product side.
- LRLenny Rachitsky
Is there anything you've learned about making OKRs work? There's a very, uh... people love 'em, people hate 'em.
- APAnnie Pearl
Yeah.
- LRLenny Rachitsky
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?
- APAnnie Pearl
Yeah. You know, when I first joined, I'd say we, you know, we didn't have this muscle well built out, right? We- 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... it was unclear how it all kind of fit together or how we were gonna measure success in that work. So that was kind of the first phase. I think the second phase for us was we developed a product strategy. We then had product team OKRs that corresponded to the- 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. 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 these really tightly integrated plans across the company around how we're gonna support the key results and ultimately, you know, deliver on the objectives. And this has been a really incredible transformation of dependency mapping, uh, you know, being able to make sure that we're- 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, you know, 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- as a business.
- 21:02 – 22:45
Changes made at Calendly to improve execution and shipping
- APAnnie Pearl
- LRLenny Rachitsky
So what I'm hearing is one of the biggest changes and learnings was to connect OKRs across from the top to the bottom, right?
- APAnnie Pearl
Absolutely. Absolutely. Yeah.
- LRLenny Rachitsky
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, like, changes you've made, in terms of how the company... yeah, and how the team's built?
- APAnnie Pearl
I think one of the biggest changes that, you know, we've made... when I first joined, again, we- we had a product that served a lot of horizontal users, right? We help solo users who are freelancers, consultants, we help, you know, sales teams, we help recruiting teams, we help customer success, we help folks in education. So it's a very broad user base and what that means is that product managers, in particular, I think had a really hard time prioritizing, right? At any point in time, it was really difficult to say, should I do, you know, work on feature A or fe- feature B without that clarity. And so I think the m- one of the most impactful things we did pretty early on in my tenure here was to hone in on overall... our- our overall product strategy, but a core 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, you know, 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, you know, historically, that would have been always a- sort of a trade-off decision and a question, and now I think we have a- a lot of rigor around who the target... you know, who our target market and their... and that persona we're going after. And so teams can use that to- to prioritize and also just deliver better value for those users.
- 22:45 – 25:21
The challenges with narrowing Calendly’s customer base and adding sales
- APAnnie Pearl
- LRLenny Rachitsky
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 gonna be selling to.
- APAnnie Pearl
I think it's one of the harder things for companies to do. Uh, so it sounds relatively easy and I think most companies believe that they have clarity around this, but then when you go, you know, down into the weeds of, you know, asking someone who's a product manager or a designer, you know, I- I- I don't know that it's always as clear because there's- 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 gonna allow you to make sure you're building something that's gonna be amazing for the people that matter most and not something that's going to be, you know, average or okay for a lot of different people.
- LRLenny Rachitsky
Was there anything that was really hard about actually executing that? Like convincing people we're gonna narrow and not worry about these people and any lessons from going through that process? 'Cause I imagine a lot of founders listening are like, "Oh, that sounds... we should be doing this, but-"
- APAnnie Pearl
Yeah. Yeah.
- LRLenny Rachitsky
"...oh man, we're leaving all this money on the table. People are gonna be pissed."
- APAnnie Pearl
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 kind of a sales motion. So, you know, when I joined Calendly, all of our ARR came from our PLG channel. We didn't have a s- you know, a sales team. We just hired a CRO who was gonna build out a sales team. And so, you know, 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, you know, explicitly started to want- you know, go after teams of users and departments of users and- and- and organizations of larger scale, everything about people, process and product all changes, right? And I touched on culture because I think that's pervasive across the entire organization. The way that things get done, you know, has to be highly integrated versus can be a bit more siloed when you're just, you know, sort of the self-service PLG business that m- in many ways runs itself through the product being well optimized. So, you know, 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, you know, the new selling motion and then the product itself, of course, has to change. So I guess that's to say the example of- of PLG and SLG or- or the direct selling motion is, you know, t- tying to your question around what are the things that need to change in order to get clear on- on your sort of your target user and I think it's highly cultural in nature across people, across process and- and even... and then obviously across the actual product itself.
- LRLenny Rachitsky
I have a whole bunch of questions about how Calendly grows and maybe we just get into some of the stuff 'cause-
- APAnnie Pearl
Sure.
- LRLenny Rachitsky
... I imagine a lot of people are interested.
- 25:21 – 26:17
Where 70% of new Calendly users come from
- LRLenny Rachitsky
First, let me ask this. I imagine Calendly mostly grows through a sign-up for Calendly, they send it to everyone when they want to book a meeting. They're like, "Oh, what is this?" And they're like, "Oh, cool, I'm gonna use this." And then they start using it and it spreads and then sales eventually find people at a company that are using it a lot and tries to get the whole company on it. Is that roughly right?
- APAnnie Pearl
Yeah.
- LRLenny Rachitsky
Okay.
- APAnnie Pearl
70% of our sign-ups come through that viral loop that you referred to and then of those sign-ups then, you know, they're usually solo users and then they start to invite team members in and then, you know, the team starts using Calendly and then usually the, you know, head of that team either inbounds to us or we, you know, have some sort of PQL data to know we should go after that, that team lead, uh, to try and have a, have a conversation around, you know, expanding Calendly across their entire organization.
- LRLenny Rachitsky
And PQL, product qualified lead, right?
- APAnnie Pearl
You got it, yep.
- LRLenny Rachitsky
Wow, what a, what a loop. What a magical way to grow that everybody wishes they could (laughs) have.
- APAnnie Pearl
It's pretty incredible, I will say. (laughs)
- LRLenny Rachitsky
Oh man.
- 26:17 – 29:23
The transition from PLG to sales
- LRLenny Rachitsky
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... Yeah, once you start product led.
- APAnnie Pearl
Yeah. You know, as I mentioned, when I joined two years ago, we just hired our first CRO and, uh, the PLG business really represented, you know, 99% of our ARR. And then over the last two years, we've, you know, scaled the sales team and our SLG motion or 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, I'd touch on in terms of early sales hires. I think the first is, you know, when you're making that transition from PLG to adding in the sales-led motion, um, because you're starting from PLG, it tends to be much more inbound in nature, right? You've got these sales reps who are working leads who have usually proactively reached out interested or, as I mentioned, PQLs, you know, they have data to tell them that this is a, you know, 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 know, you, you need to pursue more of a heavy outbound motion, more of like a hunter profile than a grower profile. So I think that's the first piece is just make sure you're, you know, you sort of, you think about the, the motion where 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, you know, outbound heavy kind of hunting, uh, sales reps.
- LRLenny Rachitsky
Just one quick question on that actually 'cause that's- that's really interesting. Uh, 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? Like is there anything to look for specifically there?
- APAnnie Pearl
Yeah, I think it's mostly background and the type of selling that they've done previously, um, more-
- LRLenny Rachitsky
Cool.
- APAnnie Pearl
... so than, than personality type. But in the second, I think the second piece that's important too, um, and I'll answer your question on that one too which is the target buyer. So when you transition from kind of PLG to sales-led or, you know, adding this direct sales motion, the buyer is usually just the department head, right? It's the head of sales, it's the head of rev ops, it's the head of recruiting and it's not, you know, 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, uh, with the target buyer in those early days. And so in the- to your, to your question around what's that mean, you know, you, you wouldn't necessarily want to bring on a bunch of sales folks who are, you know, at Oracle, right? Who are heavy in selling into CIOs in the early days 'cause that's just not who you're buyer's gonna be. I mean, I think we'll, you know, graduate there eventually, but it's probably going to start from team lead to someone in IT to eventually, you know, a CIO led purchase. But that's, you know, that's certainly several years away. And so making sure that the, the profile of the folks you're bringing on early match that target buyer in addition to match the motion around how you're gonna be, uh, acquiring, you know, customers.
- LRLenny Rachitsky
And to see that, is it similar? You look at the companies they worked at like, it's like PLG-ish company sales teams.
- APAnnie Pearl
Definitely, yeah. Exactly, yep,
- 29:23 – 31:52
How to build a great relationship with your sales team
- APAnnie Pearl
yep.
- LRLenny Rachitsky
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?
- APAnnie Pearl
The first piece it really starts with is customer, you know, 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, you know, the product team, you know, doesn't necessarily want to be bothered by sales, but I sort of flip that on the head and say sales and, 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, you know, 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 like, you know, lean on them 'cause they're talking to 10X the number of 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, you know, me make the best product decisions that I could.
- LRLenny Rachitsky
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- 31:52 – 38:14
Planning and prioritization at Calendly
- LRLenny Rachitsky
I'm curious how you prioritize work that you could be doing as a product team. There's salespeople coming at you.
- APAnnie Pearl
Yep.
- LRLenny Rachitsky
There's issues you're probably having, there's the s- founders wanting to ask you for, to step... Just, like, you know, a classic product management question, but curious if you've found any frameworks or approaches for just deciding what to actually build of all the things you're hearing?
- APAnnie Pearl
The core challenge of being a product manager, right?
- LRLenny Rachitsky
(laughs) Just to add that, like, I feel like the core job of PM is just tell people what's next, what's the next thing. (laughs)
- APAnnie Pearl
Right. That's right. And hope- and hopefully you have a, a good reasoning as to why that thing-
- LRLenny Rachitsky
Right.
- APAnnie Pearl
... uh, you know, next is gonna have the biggest impact, which is really where I start. You know, 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. It talks about how strategy is really just an integrated set of choices that outline how you're gonna win in whatever marketplace you choose, right? And so a good product strategy is gonna answer questions like, what's your sort of winning aspiration? But maybe more importantly, where are you gonna play? You know, what are the markets you're gonna go after? What are those segments of those markets? What are the personas in the segments of those markets? And then how are you gonna win with that target audience? 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 gonna play and where you're not gonna play, right? And so this really helps the product team kind of 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 kind of what that strategy is, with a, you know, playing field you're gonna go after, then I think you can divide up your product work in service of that strategy. So I'll give you an example. At Calendly, we have this sort of vision, our winning aspiration to become the best place to schedule, prepare for, and follow up on your external meetings.
- LRLenny Rachitsky
Hm.
- APAnnie Pearl
And then we've articulated kind of three horizons around how we're gonna get there. Now, the year one that I was here, the percentage of resources we spent on sort of that first horizon and, 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 weren't, you know, 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, like, a 50/50 split between horizon one and horizon two, but still no explicit investments in horizon three. And then, you know, as we're entering into 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, you know, call it 10 in horizon three. So I think just to the, to close on the question of prioritization, I think it starts with a really clear product strategy, which defines where you're gonna play and how you're gonna win, and then the work and the percentage of allocation just should feed right into that product strategy and, and how you're doing against, uh, where you need to be in order to achieve your, ultimately, your winning aspiration.
- LRLenny Rachitsky
I don't know how much you could share here, but is there a feature that is like, people keep asking for it and it hasn't been built because of the strategy, the long-term vision? Something that's like, "Nope, doesn't fit. We're not gonna do this."
- APAnnie Pearl
Yeah. I think the best example I, I can give is, you know, there's lots of small businesses and solopreneurs who would love us to have a Venmo integration.
- LRLenny Rachitsky
Mm-hmm.
- APAnnie Pearl
Uh, we have a PayPal integration, but, you know, our target market that we're really trying to go after as our primary, you know, 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 gonna help the small business, the solopreneur, the freelancer, but that's a specific, specific feature is something that would be clearly deprioritized given, uh, the current strategy.
- LRLenny Rachitsky
That's an awesome example.
- APAnnie Pearl
Yeah.
- LRLenny Rachitsky
I want to get back to the growth stuff, but before I do that, we're kind of on this topic of planning and who cares and prioritization. I'd love to know just how you do planning at Calendly. Like, how far out do you plan in detail? How far out do you have roadmaps? How often do you plan? Anything you can share there?
- APAnnie Pearl
This starts, again... Uh, I feel sound like a broken record, but with this, like, 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, uh, OKRs, and I mentioned we have about three of those this year, and then those KRAs within the company, um, OKRs, are, are measured annually, but we have milestones, uh, across a quarterly basis so we can measure progress, you know, more frequently than, than obviously on a annual or semiannual basis. So I think that's kind of at the high level. And then our, you know, obviously our product roadmaps are, are gonna be in support of those key results that we needed to deliver to the business over the course of the year, but then kind of broken down on a quarterly basis. I think one thing I'll just touch on real fast on, on kind of estimations and dates. Something we've done over the last year is, is really kind of move to a model of talking about dates and promising and committing to dates that are within our control. And so if you think about kind of the product development life cycle, you know, we can commit to a discovery effort of, you know, doing research around a certain problem space, and we can have a general sense of when we know that effort's gonna conclude. We don't know if we're gonna actually end up going and, and based on the results, whether we're gonna actually move forward with investing in that area, but that's a, a, a body of work we can commit to. From there, we then move into, okay, if this is something, a problem space we wanna go after, we're gonna go, you know, work on a couple different solutions and we're gonna go do some user testing and we're gonna 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 del- a date, uh, for delivery from an engineering perspective. And so I mean, we've gotten a lot better at c- 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.
- LRLenny Rachitsky
Yeah.That is really cool. Do you have terms for these phases, kind of like these phases you have to get through, these kind of gates? Do you have... Yeah, how do you describe that?
- APAnnie Pearl
Yeah, so the first phase, you know, we sort of just call generally discovery. Um, the second phase we call kind of solutioning. The third phase, build, and then the fourth phase is sort of launch, measure and, and iterate.
- LRLenny Rachitsky
Oh.
- APAnnie Pearl
And then we've, we've kind of designed the product development life cycle around that framework.
- LRLenny Rachitsky
So discovery for exa- for example, is that like 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?
- APAnnie Pearl
Yeah, exactly. You got it.
- 38:14 – 39:39
Strategy documents at Calendly
- APAnnie Pearl
- LRLenny Rachitsky
Sweet. Okay. In terms of the strategy artifacts, how does that look or do you have like a Google Doc with a template that you all use? What does that look like? 'Cause what's interesting about people not working at a company or working at just one company is they only have ac- like strategy documents are really hard to see and see examples of.
- APAnnie Pearl
Yeah.
- LRLenny Rachitsky
So I'm always curious what these look like. So whatever you can share about what they look like and where you put them and how long they are and that kind of thing.
- APAnnie Pearl
We have a couple different sort of layers of this. I think the first is this high level three-year strategy, and this is actually held at the company level. So it's a doc. Uh, it also has slides, uh, that have present- been presented many times to the company. And we're in the process of sort of making sure that that is part of new, new hire orientation, uh, so that, you know, everyone should understand where we're going over the next three years and, you know, then therefore how does this year's objectives fit into that? So I think that's at that level. And then, you know, from there we've got our, our product team OKRs. These generally start by docs and we write them in docs and they usually get translated into slides at some point for presentation purposes to the company, and those are, you know, sort of stored centrally in a location. And then, you know, you kind of get down to the feature level or, or the, the project level and we have, you know, different kind of templates for the teams to use, you know, based on the type of work that they're gonna be doing. And we're, we're a pretty heavy Confluence culture so we tend to use Confluence as, as one of the tools for sort of housing and storing information around the work that's being
- 39:39 – 40:21
Calendly’s product stack
- APAnnie Pearl
done.
- LRLenny Rachitsky
Cool. So maybe on that topic, what are, what else is in the stack of Calendly product team tools?
- APAnnie Pearl
We talked about roadmap planning, some combination of starts with docs, there's MURAL boards involved, uh, usually it ends in slides. Then kind of actually roadmap tracking we use Aha! and we use Airtable. Collaboration, you know, slash communication we use Slack, we use Loom. Bug management we use Jira. I'm trying to think of-
- LRLenny Rachitsky
Confluence you mentioned.
- APAnnie Pearl
... there are any other. Confluence, yep. We have Confluence as well. We, we use quite a bit. Pendo, uh, we use, we use quite a bit of Pendo to help, you know, to help educate users within the product when we're launching new features. Yeah, I think that's the main stack.
- LRLenny Rachitsky
And docs is Google Docs and slides is Google Slides?
- APAnnie Pearl
You got it. Yep.
- LRLenny Rachitsky
Sweet.
- 40:21 – 43:36
How Calendly got their first 1,000 users
- APAnnie Pearl
That's right.
- LRLenny Rachitsky
Okay. I'm gonna bounce around and go back to growth questions.
- APAnnie Pearl
Sure.
- LRLenny Rachitsky
And then I have a couple more product team questions.
- APAnnie Pearl
Sure.
- LRLenny Rachitsky
How did Calendly get their first 1,000 users story?
- APAnnie Pearl
This is a great question and I had to, to fact check it with my CEO, uh, earlier this morning, but there's actually a few really interesting things about this story, uh, 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, uh, you know, 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 kind of all the scheduling solutions that were on the market, uh, and kind of come to the 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, uh, service. And so I think he saw this as, uh, an opportunity for disruption. Um, so he raided his 401 (k) , he took out all his savings, he didn't-
- LRLenny Rachitsky
Wow.
- APAnnie Pearl
... hire, he didn't ma- he didn't raise any money.
- LRLenny Rachitsky
That's a lot of penalties, taking out money of your 401 (k) .
- APAnnie Pearl
That's true. (laughs) That's a very good point, I've never asked him about that. Um, and 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.
- LRLenny Rachitsky
Wow.
- APAnnie Pearl
Why it's important is that the first 10 users were actually customer success agents at a company in an educat- 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, you know, customer success managers, were actually using Calendly to schedule calls with parents in K through 12 and, you know, K through 12 education, and so then those parents started using Calendly for their own parent-teacher conference scheduling. And then from there, you know, school started using it and then all the parents within the school started using it for lots of other use cases and it kind of grew organically from there. So that was one piece. I think the other piece that's really important is that he, he started off by, you know, just gi- having a free tier. The, the entire product was free. Uh, 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, you know, a better product than the alternatives out there but it was also free. So the combination of the viral loop and kind of coming in through getting those first 10, 10 users as part of the, um, the firm he was using and then sort of the free aspect are I think what, what led to the first 1,000 and then, you know, 10,000 and millions of users from there.
- LRLenny Rachitsky
That is crazy. I have never heard a story like that where the team that is building your product ends up being the, the source of initial growth.
- APAnnie Pearl
I know. Pretty crazy.
- LRLenny Rachitsky
Oh my God. So many nice things happening in the history of Calendly.
- APAnnie Pearl
(laughs) I know.
- LRLenny Rachitsky
And, uh, wow, and Ukraine. So I'm actually from Ukraine and...
- APAnnie Pearl
Oh, nice. That's awesome.
- LRLenny Rachitsky
That's pretty cool.
- APAnnie Pearl
Yeah.
- LRLenny Rachitsky
Wow.
- APAnnie Pearl
They're great. We're also are.
- LRLenny Rachitsky
Yeah, and it's also interesting that it's rare that you hear a successful business starts with contractor engineers. It's often like, I think YC is like, "Do not do that."
- APAnnie Pearl
Yep.
- LRLenny Rachitsky
So that's a cool counter-example of it can actually work out, especially if they're your first users and spread it to all your friends.
- APAnnie Pearl
And, you know, they are... We also st- we still work with them and they're fantastic and they have incredible engineers, so and they're still a part of our culture, which is great.
- LRLenny Rachitsky
So Calendly got big in Ukraine sounds like initially.
- APAnnie Pearl
There you go. There you go.
- 43:36 – 46:05
The surprising new growth levers at Calendly
- APAnnie Pearl
(laughs)
- LRLenny Rachitsky
What's something that would surprise people in terms of how Calendly grows today or grew through its history?
- APAnnie Pearl
Most people probably think about Calendly as the scheduling link, and really for individual users to reduce back and forth of email and scheduling, right? 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, you know, supporting these teams of users who are in externally facing roles, and selling into departments and supporting multi-departmental deployments of Calendly across, you know, an entire organization. So I think it's still really well known as this sort of solo user tool to eliminate the back and forth of email, but the growth of wha- 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, and then multiple departments in an organization.
- LRLenny Rachitsky
It's interesting when you hear the story of a Calendly that just has so many good things happening f- like basically for free, it 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, or they, they just want to find something that was viral and then, you know, things are gonna go great, but tapers off.
- APAnnie Pearl
Yeah, you, I mean you get to a, there's only so many people who, you know, solo users who are gonna pull out a credit card. And I think once you also get to, you know, hundreds of millions of dollars of revenue scale, just the law, law of large numbers means that growth will slow. And so you kind of have to figure out where's that next growth curve going to come from. I think the, the beauty of Calendly is that while we certainly have built features and functionality to support teams and, and departments, we got pulled there, right? It wasn't one of those things where we sort of said, "We need to find our next growth lever. Let's go, you know, build X." Our, 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 kind of see in the data and see how customers are using it, that they want to be working on, you know, scheduling with their teams, that was, you know, how we sort of, sort of saw early sign that we, th- that's kind of where, where the business was gonna go in the future.
- LRLenny Rachitsky
I don't think I mentioned this. I'm a paying user of C- of Calendly. It's what I use for booking these podcast episodes.
- APAnnie Pearl
Right.
- LRLenny Rachitsky
You got me. I think I started when it was totally free and I was like, "How do these, how will they ever make money? This is too, too much power." And (laughs) .
- APAnnie Pearl
And then now you, now you, you learned that, um, it was free almost by accident.
- LRLenny Rachitsky
(laughs) Yep. I was like, "Yeah, please take my money. This makes my life easier."
- 46:05 – 48:43
Fun traditions
- LRLenny Rachitsky
What are some fun or unique traditions and cultural kind of components of the Calendly product team?
- APAnnie Pearl
A couple fun ones I thought we could talk about. One, we have a meeting called OPA, which stands for opportunity, problem, opportunity/problem, uh, assessment. And so what this is, is a, it's a meeting where basically PMs, I don't even go to it, it's a meeting for PMs to really debate and discuss with each other and kind of spar around, you know, either areas and problems that they want to go investigate or after they've gotten data back or research back from e- evaluating an, an opportunity, deciding whether we actually wanna move forward and go try to develop a solution. So it's really early in the product development life cycle of letting product managers, um, really get into a room with each other on a frequent basis and just think through things, debate, discuss, um, and I know that the, that they all get a lot of value out of that.
- LRLenny Rachitsky
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 PMs.
- APAnnie Pearl
Mm-hmm.
- LRLenny Rachitsky
And he's like, it was like, uh, like you're, like in, like in a shark tank-
- APAnnie Pearl
Shark tank.
- LRLenny Rachitsky
... where everyone's coming to destroy you. They just point out all the problems. That's all it ever is in this.
- APAnnie Pearl
I would say on this one it's kind of the opposite where I feel like everyone really needs the meeting, you know? 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 think I could imagine a world where it would be like 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 sort of judgment from me or any sort of needing to, um, act a certain way 'cause I'm in the room.
- LRLenny Rachitsky
Yeah.
- APAnnie Pearl
So that's sort of why I, I intentionally don't go. Another fun one we do is something we call competitive war gaming. So, you know, on a, some sort of time interval, so at times it's been quarterly, we'll have, assign people into groups for the quarter to own a competitor. And their job is to essentially, you know, spend a lot of time immersing themselves into the product of the competitor. Really trying to think through the lens of, do a SWOT analysis, really trying to think through the lens of where's this, uh, competitor going and, and, you know, how should Calendly think about that and, as it relates to our strategy. And so we spend a quarter doing that and then we have sort of the, 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, uh, without, you know, sort of requiring every product manager or designer to be deep in the weeds on a lot of different competitors. We can kind of bring all of that knowledge together through, uh, what we call competitive war gaming.
- LRLenny Rachitsky
That is cool. It's really impressive how you do these exercises and they're seemingly positive and friendly and constructive. It sounds like it's kind of a, there's a pretty unique culture
- 48:43 – 52:07
“Focus wisely” and other aspects of Calendly’s culture
- LRLenny Rachitsky
at Calendly. I'm curious if there's anything else that's kind of core to the values or the way that you think about the principles of building product at Calendly.
- APAnnie Pearl
What I touched on earlier is really core to how we build product, which is honing in on this target, um, user and honing in on our target market. I do think it's, it's quite rare. I think at 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. Uh, it's pretty deeply embedded into our culture and so I think it, you know, 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 would work in every organization. I think many organizations really struggle to say no and they're kind of, you know, always adding more onto the plate versus taking off. But I do think if you, you know, from an ethos perspective, there is something around focusing and the ability to focus to therefore g-... deliver the highest quality of product that you can to your target customers. That is unique and I think it starts with, you know, 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.
- LRLenny Rachitsky
Is there anything else you do to instill that? Sounds like it's a core value. Do you put posters around the office? How else do you keep people focused?
- APAnnie Pearl
We're a fully remote company.
- LRLenny Rachitsky
Okay.
- APAnnie Pearl
So now you've got my brain going on are there, you know, some sort of virtual sticky notes that you could get people to put on to their, uh, to their laptops to remind them.
- LRLenny Rachitsky
Backgrounds to show off-
- APAnnie Pearl
Yeah. Exactly. Yeah. It's embedded into a lot of the documentation, right? So it's embedded into the l- the templates that I talked about in terms of when, you know, even e- everything from sort of the way we structure that OPA, uh, document that folks are, are gonna be, you know, working on and debating, to when they go to create the actual sort of PRD, you know, when, when teams come in to present as part of, you know, sort of our, our product reviews, you know? We sort of, we have a, we have a template that sort of 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 gonna solve their needs, you know, better than any alternative that, that there is on the market. So I think there's lots of different kind of reinforcing, uh, mechanisms to, to that focus.
- LRLenny Rachitsky
I feel like sometimes things like that come from, like, a big problem the company had and then, like, you, you index way the other side, like focus, here's the four people we will build for becomes, like, instilled in the culture.
- APAnnie Pearl
And I think you're right, right? I mean because Calendly started as such a horizontal product, which was amazing because that's how it grew so virally, right? And so it, it had the entry, the wedge into scheduling and how we sort of, our first horizon in becoming the best horizontal scheduling automation platform was because we had that horizontal focus. And so that was, it was a blessing, but as we think about sort of me transitioning to horizon two, which is really about deepening our support for these, you know, teams and departmental users as well as verticals, that's I think the inflection point where we said, "In order to, to shift us from horizon one to horizon two, we need to be making some, 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 actually, it's a really good point. We, 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.
- 52:07 – 54:57
Learnings from Box and Glassdoor
- LRLenny Rachitsky
Before Calendly, you were at Box. Before that, you were at Glassdoor. I'm gonna ask two different questions, you can pick which direction you want to go. What would you say are kind of the biggest differences culturally between these three? Like if you had to bucket here's how I'd describe Glassdoor, Box, Calendly. Or what did you take from those two places that kind of, that you bring with you to Calendly and future opportunities?
- APAnnie Pearl
I love this question. So they're all different. Um, which is why I've, I just feel so fortunate to have had experiences that were, were, 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, uh, and I was on the enterprise product management team. So I spent a lot of time, as I mentioned earlier, talking to customers in, 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 customer C wanted, not only would that be, you know, wasted effort to do th- it three times, but more importantly, what they wanted me to go build was gonna have a negative impact on the end user experience, and preserving that end user experience was so critical. So, you know, learning how to ask the right questions to understand the actual problem and then build a solution that's gonna be most scalable to that problem set across lots of customers was, was probably my biggest learning from Box. Moving to Glassdoor, totally different business model, right? Glassdoor is actually really more of a consumer business, and you know, 60 million unique users go to Glassdoor every month and it's a, it's a marketplace, uh, between job seekers and employers and, um, it's highly, highly dependent on the consumer engagement, right? 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, right? The consumer business and the B2B. And so I learned all about, you know, sort of how do you build consumer products? How do you think about optimization of a funnel? How do you think about building up a growth team and, and growth as a discipline? How do you use data, um, and AB testing to make decisions? So I think that kind of consumer mentality in how you approach product, I then have brought with me to Calendly, uh, which is really a blend of both, right? (laughs) Uh, Calendly is first, as we've talked about, a PLG business, and it looks a lot more like a consumer business, uh, like Glassdoor's. And then it's got this direct selling business that looks a lot more like Box's enterprise business. So I, I think I've been able to take kind of lessons learned from both Box and Glassdoor and, and kind of apply them together to Calendly.
- LRLenny Rachitsky
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-
- APAnnie Pearl
(laughs) . That's great.
- LRLenny Rachitsky
... looking at reviews of-
- APAnnie Pearl
And recruiting. (laughs)
- LRLenny Rachitsky
And recruiting, yeah, yeah. Not looking for anything new.
- 54:57 – 58:10
The Skip Community
- LRLenny Rachitsky
Okay, final question. You're part of something called the Skip Community, which I believe Nikhil 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, uh, might be a fit.
- APAnnie Pearl
Yeah, as you mentioned, abou- about two years ago, Nikhil, uh, who was the former CPO at Credit Karma and is now a VP of product at Meta, got a small group of CPOs together who were all kind of going through similar phases of companies growth, right? Late-stage growth companies. And, you know, we all were facing the same challenges in our roles and, and he kind of formalized this community as a way to help us kind of gather advice from one another, you know, talk through how to manage challenges we're facing, and just make us more successful in the roles. And we always joke, you know, we're like the support group. We meet on Sundays and it has been incredibly valuable as I've sort of, you know, gone through the last couple of years in my role at Calendly. Um, 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 kind of 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, right? And so we're experimenting with a couple of different interesting ways to help product leaders grow. One of them is, you know, we're, 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 CPO hire really hone in on what they're looking for. And partnering with some talent partners we know to really h- try to increase the success that they find the right candidates. That's something interesting we're doing. Uh, we also launched a, uh, recently launched a podcast covering some topics like, you know, how do you manage the next job search? How do you avoid burnout? Uh, breaking down things like equity and, and other kind of, you know, timely topics. And then also we just have a, we have an active Discord server where we've got all sorts of channels from topics like how to, you know, uh, manage the CEO/CPO partnership, compensation, uh, you know, even sharing planning, uh, even sharing some advising opportunities or other CPO roles that we know kind of come across our radar. So it's been a really, really cool, uh, kind of experiment to see how the power of the community... And I know, Lenny, you do a ton of stuff around community, you know, how that has helped all of us, I think, be just more effective in our roles and, and feel like we have a group of people who are behind us, supporting us during, you know, what is a, a very hard role.
- LRLenny Rachitsky
I love this. I imagine when people look at a CPO, they imagine they just like know everything already.
- APAnnie Pearl
Mm-hmm.
- LRLenny Rachitsky
They have a bunch of friends in the same role, but I think in reality it's like kind of a lonely role a lot of times.
- APAnnie Pearl
Totally.
- LRLenny Rachitsky
And so I could see the power of something like this. Just to help people understand, who, who'd be a good fit for this? How do they go find it? And yeah, what's like the site and...
- APAnnie Pearl
The best thing to do is just follow the Skip Community on LinkedIn and then, you know, we're, you know, sort of targeting sort of head of products at, you know, call it series B, C and beyond up to, you know, late-stage growth companies and up to CPOs. So I'd say start by kind of following the Skip Community and if you see folks in there who are in the group, you know, reach out to them to, to get a sense of, uh, what it's like and, and what it would be like to join.
- LRLenny Rachitsky
And then it sounds like if you're a company hiring a CPO, maybe reach out to you or is that it?
- APAnnie Pearl
Yeah, that'd be great. That'd be great. Yeah.
- LRLenny Rachitsky
Okay. And they do that by going to LinkedIn also and looking for the Skip Community?
- APAnnie Pearl
Yeah, that'd be great.
- LRLenny Rachitsky
Okay, cool. We'll put all the links in the show notes as well.
- 58:10 – 1:01:48
Lightning round
- LRLenny Rachitsky
Well, with that, we've reached our very exciting lightning round. I've got six questions for you. Are you ready?
- APAnnie Pearl
Let's do it.
- LRLenny Rachitsky
What are two or three books that you recommend most to other people?
- APAnnie Pearl
Playing to Win. So I, I re- referenced that one earlier. Good to Great, uh, and Hooked.
- LRLenny Rachitsky
Awesome. What's a favorite other podcast that you enjoy other than maybe this podcast?
- APAnnie Pearl
I think I got introduced to you fro- by Harry from The 20VC, I think. But if not, either way, I'll cross-promote his podcast-
- LRLenny Rachitsky
Mm-hmm.
- APAnnie Pearl
... uh, which is a great one.
- LRLenny Rachitsky
Yeah, Harry's responsible for this podcast. I was on his podcast and he's like, "Lenny, you should be doing a podcast."
- APAnnie Pearl
"You gotta do it."
- LRLenny Rachitsky
Yeah, "What are you doing?" So he's-
- APAnnie Pearl
I love it.
- LRLenny Rachitsky
... he's the godfather of this podcast, Harry.
- APAnnie Pearl
He is. That's great.
- LRLenny Rachitsky
What's a favorite recent movie or TV show? And you cannot say White Lotus.
- APAnnie Pearl
I, uh, I have two young kids, so whether I like it or not, Sing 2. Uh, it's a great movie, especially if you have young children.
- LRLenny Rachitsky
Sing 2. So it's like the second of Sing?
- APAnnie Pearl
It is, it is.
- LRLenny Rachitsky
Okay, cool.
- APAnnie Pearl
Distinct from Sing 1. Sing 2 is better.
- LRLenny Rachitsky
It's better. Okay, cool. I haven't s- I haven't seen it. Uh-
- APAnnie Pearl
I, I would hope you haven't.
- LRLenny Rachitsky
Okay, cool. Favorite interview question that you like to ask people you interview?
- APAnnie Pearl
Talk me through your biggest product flop. Uh, what happened and what did you do about it?
- LRLenny Rachitsky
What do you look for in an answer? What's like a sign of something good in their answer?
- APAnnie Pearl
People being brutally honest around how bad it was and why it failed. You know, 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.
- LRLenny Rachitsky
Awesome. Next question, I think you might have answered, but what are top five SaaS products you use day-to-day, either at work or home, whatever?
- APAnnie Pearl
Slack, Miro, Loom, Pendo, and Confluence.
- LRLenny Rachitsky
Awesome. And these are like actually an- unlike other people's answers, so that's really interesting. Kind of a unique stack you got there.
- APAnnie Pearl
Love it.
Episode duration: 1:01:48
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