How Calendly Scaled Into the Enterprise with Kate Ahlering, Calendly

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What separates a good go to market organization from a great go to market organization is the ability and capacity to use data to drive decision making, which sounds very obvious, but is often hard to do really well. And when you're small, the data is still hard to get in many cases, but just explodes in terms of complexity when you're scaling. So super important to drive deliberate focus. I need some traction. You need some traction. Let's get some traction.

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Kate and I know each other from way back, like seven years ago, which is decades in the tech world. You've obviously seen this playbook around pairing PLG and enterprise sales in multiple companies. It's now almost a buzzword. It's taken off popularity. What convinced you to start the journey again at Calendly and how did you know it was the right opportunity?

Yeah, thanks, Kyle. It's great to be up here and it's nice to see all of you and be in Vancouver. I joined Calendly because it sounds cliche, but I just fell in love with the problem. We've all gone through the pain of ping pong scheduling, and we're in the midst of this transformation and the reshaping of the future of work. And so when I thought about the problem in the context of what's happening in the world, I was like, okay, that feels like a pretty big opportunity. And the more I dug in, I validated that hypothesis. It is a huge market. Scheduling Automation is a $20 billion market. Calendly has 50 million users and 10,000 different organizations that use the product. And so when I looked at all of this, the cherry on top was the opportunity to add an Enterprise selling motion to one of the canonical PLG companies out there. And when you look at all those factors, it was a no brainer.

How many of you are Calendly users? Raise your hand.

Woo.

Just a few.

Thank you all. I am too.

Yeah, that's awesome. Yeah, same here.

It was actually part of my experience. I took six months off in between jobs and as I was dipping the toe back in the water as a part of the recruitment process, I began using Calendly and it was a game changer for me just as an individual, as it is for many of our customers. And so that was part of the proof in the pudding too.

And so Calendly's been wild success story. People know it for the viral loop, the self service nature of maybe buying for an individual or as a small team. But sales is a new function. And so as the kind of first CRO of Calendly in terms of really building out this enterprise sales motion, take us back to January 2022. Like how do you think about your first 30 days and really building that motion from the ground up?

Yeah, absolutely. I think some of the wisdom around your first 30 days is you should really go slow, you should really listen, the whole two ears, one mouth adage. And I think for most of us, if you've joined a tech company that's in hyper growth mode, you just don't have the luxury of sitting back and listening for even 30 days. And particularly definitely not the 90 day wisdom that's been shared. I would encourage everyone to have a bias for action in that situation. And that's definitely how I approach the challenge. I can tell you just as an anecdote, in the first 30 days I was handed a pretty ambitious growth plan, tops down revenue number. And so there was some validation that needed to happen from a bottoms up perspective and then key strategies that needed to be built so that we could believe that very ambitious number in your first 30 days. When I thought about what needed to happen, we needed to build a plan just as anyone who owns go to market organizations would do. And the key components of my plan at the time were really focused on building these key selling motions in the upmarket segments. So for us this is really mid market. These are enterprise selling motions and putting a great deal of focus on what the initial ones would be. Outside of that, of course, we're also doing a ton of team building. We're hiring, we're trying to make sure that we're getting the right talent in the door. And then the third component is really about the ops infrastructure that you need to stand up as a part of a growing go to market organization. It's absolute key. I somewhat joke very often Calendly is almost a 10 year old company, but the selling motion and adding a real tops down sales team is less than 2 years old. So I like to think that I'm leading a two year old organization inside of a ten year old organization. And so there's a lot of go to market architecture that needs to be around things like just sales process, sales methodology, comp plans, these sort of like unsexy things that need to happen because they're the critical underpinnings of your organization. So that was at least a lot of the thinking and maybe not all the doing in the first 30 days. But I would definitely recommend not just sitting back and waiting. You just don't have the luxury of doing that in an environment like Calendly.

Great advice. And now everyone in this room is probably thinking about how to accelerate revenue growth. What are things they can do quickly to scale faster. So over the past few months, what are some of the tactics or strategies that you've put into motion at Calendly?

Yeah, absolutely. So when I think about Calendly, and really this is the opportunity for many in the PLG space, we have a couple of unfair advantages. And the first is when we engage with a customer, we're of course looking through the value or the lens of value all the time. We always want to be driving customer value. And one of the advantages that we have is often there are people not just using Calendly inside an organization, but we have raving fans inside of an organization very often. And those raving fans help us create these viral loops and virality inside an org so that it does spread from maybe an individual user to a small team, to an entire department. And if I do my job well, then to an entire organization. And so we have that out of the gate. The role of sales and really what we've been focused on strategically is to help us get from those small groups, those small teams that are using the product very often successfully and getting tremendous value from Calendly. But the role of sales is to make the leap from those small teams to get above the line to the right altitude in the organization to have more of a business value conversation. The PLG user, the individual user, loves what it is, loves what it does. They're often very technical. And the role of sales is to get to what it means for your business. And when you can deploy a tool like this across Your organization. Let me tell you about the value that we can create. And so much of our strategy is about building the playbooks to align and connect the dots from those users into the enterprise space. But again, we have the unfair advantage of the data to be able to sort through and help our sellers with that.

Yeah, it's a great point and I think there used to be some thoughts that folks had that said the self service motion would just naturally work on its own. You don't necessarily need to add sales, but I think folks have started to realize it's a different motion and it's a really important set of strategies and conversations to drive much larger deals and stickiness inside of an organization. Because that viral user who champions the product from the bottom up, they're probably not the one writing the check for a 500k deal across an organization. And they fundamentally care about different things. So you can work with them or document their stories, but if you only are talking to them, you're probably going to get stuck in just a small piece of the organization.

Yeah, you're absolutely right. And that's the transition point that we're in and probably will be in for a while. And many companies go through is again going from these small set of users to an organizational value hypothesis with someone who has influence at the right altitude is a different motion altogether. So that's a key part of our focus at the moment.

And one area I want to spend some time on is how do you prioritize accounts? So you've got a lot of data, especially quantitative data around product usage, the kinds of companies that are signing up for calendly. What signals do you and your team look at to say hey, this is an account that should deserve sales touch points and at this specific moment in their journey?

Yeah, I actually for my money, I think this is what separates a good go to market organization from a great go to market organization is the ability and capacity to use data to drive decision making, which sounds very obvious but is often hard to do really well. And when you're small, the data is still hard to get in many cases, but just explodes in terms of complexity when you're scaling. So super important to drive deliberate focus. Two of the ways that we do this from both an inbound and an outbound perspective today is we gather product data which is unique to a PLG company and you have access to that and we develop two different types of opportunities or leads for our folks. The the first is a product qualified lead and many of you have heard of this pql and this is a combination of both product data, usage data, and also firmographic data. So I'll give you an example. We could have a customer sign up, activate in a trial, perhaps they invite several members of their team and we can see that they did that. And then perhaps they initiate a key integration. That in and of itself is pretty interesting, but it gets very interesting when it's a customer in our ideal customer profile or icp and potentially they have a director level title. So we can bake a bunch of inferences around, okay, this is the right type of account. It's the right type of person that has the right influence that would understand value. And they've been initiating all these actions. That's a lead that should go to our team and that is a trigger point for us to have engagement across the sales team. The second concept that we're building a framework around is very similar, but it's called a product qualified account. And so if a lead is an individual, an account is really a subset of users where we extract the data and we're able to say again, firmographic data. This is the right ICP for us. And this subset of users have done enough key actions inside of our account that we know across a huge swath of data usually leads to a valuable conversation at the end. And so we serve that account to a sales rep for outbound sales engagement. So that's just two of the ways that we're using some of the data that's super valuable to us.

Yeah, I really like that. And we hear hear this term product qualified lead or PQL a lot. But the product qualified accounts get very interesting as well. And that's where you might have multiple users inside of an organization or multiple use cases. But if this is the account that's worth prioritizing, that's something where you wanna send that to that sales rep and they're gonna develop a plan for how do we break into this account, how do we land and expand?

Yeah, and we use it at the strategic level to help us segment. We use it at the strategic level to help build territories for our teams and of course serve these leads in a just in time fashion. But it drives multiple levels of prior for us. Even when our AES come in to work for the day, come in at their homes to work for the day, they have a set of prioritized accounts that they can see based on the actions that are happening in the product and where we want them to spend their time. And I think we're all trying to Figure out ways to use data in a really unique way. And it feels like every day the data gets harder and you have less insights. But some of the ways that we're using the data that's proprietary to Cal only.

And obviously we'd love to talk about success stories and everything being positive, but PLG companies often run into really significant challenges when trying to move up market and sell into the enterprise. What are some of the most common failure points that you see that you would advise folks in this room to be mindful of?

Yeah, and I'll give you some of my lessons learned. If any of you have been or own enterprise sales teams. Enterprise selling is hard, period. It is just hard to tackle and navigate. It does yield big rewards and so if you do it well, there will be a pot of gold at the end of the rainbow for you. But there's a reason that not everybody does it. It's really hard. So two of the failures that I've either experienced or see out there that I'll highlight for the purposes today is when you think about your pricing and packaging. Many PLG company, almost all have transparent pricing on the website. And so you'll see you can run from an individual user to a team user, up to an enterprise package. If you don't have enough differentiation between either the individual user or the team's plan and your enterprise plan, if you don't put enough of a wedge between those plans and status quo, then you won't have any leverage for your sales team to go have that conversation about the value that could get realized at an enterprise level. Now this could go either way. If you build too much into the enterprise plan, you risk losing those raving fans I talked about at the beginning. And as an example, perhaps you just over permission, you build way too many permissions and all the things that they love to do, they're no longer able to do. That would be an example of going too far. So it is this delicate balance of making sure you nail the leverage inside your pricing plans. So that's the first one, the second one that I would say and it's part of what we're going through at Calendly and a mistake I hope to avoid is you can get very stuck on positioning features and in the early stages of your company you should. That's why users are activating, that's why they're signing up. It's the things that are going to make their life easier as a user or small. However, when you think about those users and trying to move them again to the enterprise plan. Eventually you have to go through this transition where you start talking about business outcomes and value. And so that's an important transition that any young company can make. But if you wanna be successful into the enterprise, you absolutely have to again, move from the is does to the means for a business.

And I think to underscore one of your points, to have that pricing and packaging differentiation, you have to be ready to have a product that can serve the enterprise too. And so you might be getting demand and see that as a signal that the enterprise wants to buy our product, but you then have to be able to meet that demand too.

Yeah. Which is a really important point to make. I agree.

And so you joined in January, it's been roughly eight months. How have you been able to tell whether what you've been doing is working? What are some of the metrics that you track and leading indicators of success?

Yeah, I would love, and I think most of us in this room would love to say we look at all the data and you want all the data all the time. And that's certainly my mentality. We look at the traditional top of funnel metric volume velocity value across a bunch of different dimensions. The thing that we've gotten really specific about and if you go in our Revops team teams at Calendly, they'll tell you I've become just maniacally focused on cohorted conversion rates, but not generally for very specific types of accounts. And so we've had a focus over the last year and a half to really get to these upmarket high value accounts. And so we're watching them come into the funnel. If they meet our ICP for these types of characteristics, we watch them come into the funnel and the leading indicators are not, are they, are they closed? Are they closed one and are they going to be at the value that we want? The leading indicators, Are we converting enough in the first 30 days, are we converting enough in the first 60, 90 and are we converting for the use cases that we are specifically targeting? So we think our position is where we drive the most value right now today at Calendly is in the sales use case, in the customer success use case and in the recruiting use case. So as we see these upmarket accounts that we believe to be high value coming into the funnel, are they from users inside of our key use cases and are they converting at or above what we expected them to convert? So I spend a lot of time obsessing about that along with all of the other, the standard metrics, cac and so forth.

And something we talked about earlier that I think is just an interesting nuance here is that you had mentioned you're looking at cohorted conversion rates and that's inclusive in my mind of whatever channel that customer chooses to buy. So it might happen that a sales rep does a lot of really great work with an enterprise customer and that customer decides to start on a self serve plan, which you might look at that and say sales isn't doing their job or why isn't this revenue coming through the sales team? But in a PLG company, the channel is an option that the customer has, but sales is really doing the work to drive that conversion and that experience. And it's fascinating to think about, but you might even want to start compensating reps for deals that they touched pre conversion but that bought via self serve and, and not thinking of it as two separate funnels, but thinking of it as one broader revenue number.

Yeah. And when we look at the data behind. So the theory there is of course they get started, they're going to have quick time to value and they're going to convert and then hopefully expand. And the data that we see backs that up. And so we actually have no issue with that whatsoever. If someone enters into a free trial, regardless of their ICP use case, their title, we believe that the vast majority of the time that's going to be a positive event for them. They're going to see value from the product, they're going to see it fast, and in doing so they're very likely to expand. And we see that in our net revenue retention number. So for our teams, we actually encourage that. That's not a bad outcome. Moving someone into a trial or even starting someone with just a few seats is not a bad outcome because we have faith and belief in the product over time and the value that it's going to provide to that organization.

What final lessons learned or tips do you have for folks thinking about how to pair sales with product LED growth?

Yeah, so I would say if you look at some of the most successful publicly traded software companies out there that have a PLG motion, and Kyle's written about this in his newsletter, so this is where I learned this. And you should all subscribe to Kyle's newsletter. If you look at the snowflakes, the asanas, the datadogs of the world, they all have material portions of their business coming from enterprise accounts. So there is a little bit of mythology around PLG leading to the promised land alone. It's the combination of PLG and the sales led effort that has led to the success of those companies. And we're certainly on the path to do that. So what I would say is it's a commitment. If you're running a PLG company today and you're considering adding a sales team of real humans who are going to be out there, it's going to take a while. Building an upmarket sales team takes a while. It's a huge change for your organization. You have to spiritually be aligned to that. And if you can get those things right and be patient, look for your leading indicators, but be patient on the road, you'll crack open tam, and you're very likely to again, significantly improve your product.

Thank you, Kate. And for folks that are looking to pair sales in plg, I hope you took away some interesting lessons. And it's been fascinating to see the rise of this pairing that we used to think where it couldn't fit together. But now folks are, I think, waking up to the fact that this is a really great partnership that can happen between product and sales if we let it.

Yeah, absolutely. And it just, it goes back to all the basic fundamentals. You have to have goal alignment, you have to have commitment across the organization and it's gotta be an imperative for you. It can't be blending in. The hybrid approach here cannot be a part time initiative. It needs to be a focus of the organization. And so that's what I have seen lead to success and encourage all of you to think about as well.

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