YouSaid · the spoken record

Annie Pearl

lines on the record: 63
first: 2023-02-26
most recent: 2023-02-26
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“Finding me best place online is LinkedIn. And then in terms of being helpful to me, one, we're hiring at Cally, so explore open roles on the product team at Cally if you're interested. Share any feedback for me on this episode at a.Pearl at calonly.com. And then as we talked about, we'd love to have you follow the Skip community on LinkedIn as well.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so we just launched a new feature that I'm loving personally called Customize 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 kind of 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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 RAR the answer in terms of how bad it was and why, the better.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“I think I got introduced to you by Harry from the 20BC, I think. But if not, either way, I'll cross-promote his podcast Which is a great one.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“The best thing to do is just follow the skip community on LinkedIn and then we're sort of targeting sort of head of products at, you know, call it series B, C, and beyond up to late stage growth companies and up to CPOs. So I'd say StarkBy 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 get a sense of what it's like and what it would be like to join.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Know Lenny, you do a ton of stuff around community, how that has helped all of us be 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”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“One of them is, you know, 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 Cental partners we know to really try to increase the success that they find the right candidates. That's something interesting we're doing. We also launched a recently launched 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 a we have an active Discord server where we've got all sorts of channels from topics like 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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“As you mentioned, about two years ago, Nikhil, who was the former CPO at Credit Kerma 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 company's growth, right? Late stage growth companies. And we all were facing the same challenges in our roles and he kind of formalized this community as a way to help us kind of 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, 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 Callendly. 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 different interesting ways to help product leaders.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Love this question. So they're all different, which is why I just feel so fortunate to have had experiences that we're 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 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”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“And I think you're right. I mean, because Cal only started as such a horizontal product, which was amazing because that's how it grew so virally, right? And so it had the entry, the wedge into scheduling and how we sort of our first horizon of 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 sort of transitioning to Horizon 2, which is really about deepening our support for these teams and departmental users as well as verticals, that's, I think, the inflection part where we said in order to shift us from Horizon 1 to Horizon 2, 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. 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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Or a fully remote company. So now you've got my brain going on. Are there some sort of virtual sticky nodes that you could get people to put onto their laptops to remind them? Yeah, exactly. Yeah. It's embedded into a lot of the documentation, right? So it's embedded into the templates that I talked about in terms of when everything from sort of the way we structure that OPA document that folks are going to be working on and debating to 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 sort of keeps reinforcing who's the target customer, who's the target user within that customer base, what are their needs, and 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 kind of reinforcing mechanisms to that focus.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 Cali'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 Cali 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 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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Relates to our strategy. And so we spent a quarter doing that, and then we have sort of 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, 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 what we call competitive work gaming.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“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, oh, 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 meeting to act a certain way because I've been the room. So that's sort of why I intentionally don't go. Another fun one we do is something we call competitive work aiming. So on some sort of time interval time has 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 SWOT analysis, really trying to think through the lens of where's this competitor going and how should Calan only think about that as early as early.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“A couple 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, is 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 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 early 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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I mean, you get to a, 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 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 beauty of Calendly is that while we certainly have built features and functionality to support teams 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 customers really pulled us there by the way that they were using the product.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Most people probably think about Calanly as the scheduling link and really for individual users to reduce the 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 supporting these teams of users who are externally facing roles and selling into departments and supporting multi-departmental deployments of Cali across 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 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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“And you know, they are, we also work with them. They're fantastic, and they have incredible engineers. So they're still part of our culture, which is great.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“That was one piece. I think the other piece that's really important is that he started off by, you know, 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 kind of coming in through getting those first 10 users as part of the firm he was using and then sort of the free aspect or I think what led to the first 2000 and then you know 10,000 and millions of users from there.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“That's a very good point. I've never asked him about that and hired an outside development firm actually out of the Ukraine to build the first version of CalNY. So that's the background on Kalani. 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 TOP 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 CalA to schedule calls with parents in K through 12 and K through 12 education. And so then those parents started using Cali 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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Great question. 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, founder, has 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 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 service. And so I think he saw this as an opportunity for disruption. So he rated his 401k. He took out all of his savings. He didn't hire it. He didn't raise any money.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“We talked about roadmap planning, some combination of starts with docs, there's mural boards involved, usually it ends and slides, then kind of actually roadmap tracking, we use AHA and we use Airtable collaboration slash communication. We use Slack, we use Loom, bug management, we use JIRA Trying to think of Confluence, yep, we use Confluence as well. We use quite a bit. Pendo, we use quite a bit of Pendo to help educate users within the product when we're launching new features. I think that's the main stack.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 called at the company level. So it's a dock. It also has slides that have been presented many times to the company, and we're in the process of sort of making sure that that is part of new hire orientation so that everyone should understand where we go on 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. They usually get translated into slides at some point for presentation purposes to the company. And those are sort of stored centrally in a location. And then you kind of 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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so the first phase, you know, we sort of just call generally discovery. The second phase, we call kind of solutioning. The third phase build, and then the fourth phase is sort of launch measure.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 lifecycle, 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 is 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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“This starts again. I saw it 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 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 need 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 kind of estimations and dates. Something we've done over the last year is really kind of moved to a”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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's a specific feature is something that would be clearly deprioritized given the current strategy.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Investments in Horizon 3. And then, you know, as we're entering into year three, now we've significantly scaled back the investment in Horizon 1. That's about 30%. And then we've got 60% in Horizon 2 and call it 10% in Horizon 3. 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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 playing field, you're going to 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 Cali, 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. And then we've articulated kind of 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 sort of that first horizon and the second horizon was about a 70-30 split, and we put 0% of our resources on Horizon 3. 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 1 and Horizon 2, but still no explicit.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. 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, 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 the segments of those markets? And then how are you going to win with a 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 going to play and where you're not going to play, right? And so this really helps the product team.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“First piece it 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 flipped that on the head and say sales and sort of the go-to-market teams in general could be a 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 because they're talking to 10x them on we're customers that I was able to ever talk to within any given week, really lean on them.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Eventually, but it's probably going to start from Ting Lee to someone in IT to eventually a CIO led purchase. But that's certainly several years away. And so making sure that the profile of 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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I think it's mostly background and the type of selling that they've done previously, more so than personality type. But in the second, I think the second piece that's important too, and I'll only answer your question on that one too, which is the target buyer. So when you transition from kind of PLG to sales-led or adding misdirect sales motion, the buyer is usually just the department head, right? It's the head of sales, it's the head of RevOps, 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, you know, at Oracle, right? Who are heavy in selling into CIOs in the early days? Because that's just not who you're going to buyer is going to be. I mean, I think we'll, you know, graduate there.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Team member, then you might need after 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 sort of, you think about 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 outbound, heavy, kind of hunting sales reps.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“You know, 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'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, 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 someone who has usage within their team and therefore we should reach out. And so that's a very different profile of a sales.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“70% 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, you know, the team starts using Cali, 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 calendar across their entire organization.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 that's to say the example of PLG and SLG or the direct selling motion is tying to your question around what are the things that need to change in order to get clear on your sort of your target user. And I think it's highly cultural in nature across people, across process, and even, and then obviously across the actual product itself.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 a world 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, right? 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, you know, sort of the self-service.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 lot of rigor around who the target 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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“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, right? 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 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 future 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 overall 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 features”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Mapping, you know, being able to make sure that we're pulling all the levers across the organization to drive our most important objectives. 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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, you know, when I first joined, I'd say we, you know, we didn't have this muscle well built out, right? 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 kind of fit together or how we were going to 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 that product strategy, but they were really contained in 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 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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Right. That's right. Yeah, trying to sell two, and then sort of 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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Tools to manage users and groups at scale. And the second piece of that is also kind of departmental leaders. So as Kelly's selling into or being used by a sales organization, the head of sales is not the IT admin, but they are a kind of a teams admin who needs to manage their organization within Cal only. 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 Cally 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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“Think about that. Yeah, so we have a core team who's really responsible for the core end-to-end user experience. And in many ways, they're both building, doing feature development. And then they're also doing growth work, right? 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, you know, growth work to think about 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. And they're really thinking about two different personas. One is the sort of IT admin, right? The sort of person who needs to make sure that Cal only is secure and that they have all the reporting mechanisms to be able to manage their account and all.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“So, the structure was there that way. At the 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 ahead of design to really build out that function. And then that head of design is sort of a peer partnering with the different heads of products across the product management organization as well.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 Calhoun, I 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 Cali. I think at the end of the day, the real benefit of the structure is really to say, you know, we want”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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.”
2023-02-26 · Lenny's Podcast · Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) · IDENTIFIED FROM THE TRANSCRIPT · source