Annie Pearl (Calendly): Building Enterprise Products

Annie Pearl: The need for communication between product and the rest of the company exponentially goes up in value when you layer on top of the product- led growth motion a sales- led growth model.

Blake Bartlett: Welcome to BUILD, the podcast from OpenView. I'm your host, Blake Bartlett, and the show features conversations with software founders, leaders, and investors. Each episode unpacks a new key insight on how to build your company and navigate the fast- changing world of software startups. At some point in every PLG company's life, you're going to have to build for the enterprise. This is what the journey looks like. Most companies start by focusing on individual end users and prosumers. From there, you build a team's product and start selling some real B2B deals, and you eventually go from small teams to larger teams, maybe even whole companies. Albeit, usually smaller companies like startups at first. Then at some point, your bottom- up adoption reaches its final destination. You've successfully grown from the bottom all the way to the top of the top. The C- suite of the largest organizations in the world. Congratulations, you have arrived. Welcome to the enterprise. But don't pop that champagne bottle quite yet because now you have to build an enterprise product. That's a hard thing to do. Embracing the enterprise means going from one to many. One product to multiple products. One funnel to multiple funnels. One go to market motion to multiple, combining both bottom- up and top- down. Going from one to many in all these different areas increases complexity exponentially, and complexity breaks things. Namely, it breaks people, process, and product. Thankfully, our guest today is Annie Pearl, Chief Product Officer at Calendly, and previously she was Chief Product Officer at Glassdoor. She has mastered this journey to the enterprise, and she shares her playbook with us today. Let's dive right in with Annie Pearl. Well Annie, thank you so much for joining us here on the BUILD podcast. It's great to have you on the show.

Annie Pearl: Great to be here, Blake.

Blake Bartlett: We're talking about a common thing that every PLG company faces. At some point, PLG businesses need to embrace the enterprise. What does that look like in practice for your average PLG business? What have you seen?

Annie Pearl: Yeah, I think maybe it's important to start with why. Why do all PLG businesses at some point need to embrace enterprise? There's usually two reasons that maturing PLG companies hit a point at which they need to start thinking about embracing the enterprise. The first is that self- service model naturally begins to slow in growth as companies just grow in large size in terms of revenue scale. When you're getting into the hundreds of millions of dollars in PLG revenue naturally law of numbers, the growth rate year over year is going to slow. The second is to become really ubiquitous across departments in a company, or across several departments, you really have to engage in tops- down decision makers to be able to meet their security and compliance needs, to ultimately roll out your product at scales. So the introduction of the sales- led model on top of this PLG model can actually re- ignite growth but also accelerate it. If you can get these two flywheels, the PLG and the sales- led flywheel, to be working in tandem, you can actually produce compounding effects on the business. Just starting with the background of why does every company go through this at some point. Then I think when you go to make the shift effectively, there's really two parts of the transformation. One is on the product side, and the other is on the go- to- market side. On the product side, you're moving from serving just the needs of individuals to teams of users. You're going from serving the needs of individuals to department leaders, from individuals to the IT buyer. You have a shift of the audience of who the product needs to be solving problems for. Then on the go- to- market side, you go from maybe no sales team to building a sales team from the ground up or a in- bound sales team to maybe an out- bound selling motion. Similarly on marketing, similarly on customer success. Across the whole organization, you're going from simple to complex or from one model to building new models across the organization.

Blake Bartlett: It's an inevitability, and I have definitely seen that from my perspective as well. There's just a point at which you either get pulled into the enterprise, and people start just asking, " I want to go wall to wall with this product, but I need X and Y and Z in order for that to happen." There's a pull dynamic. Or, like you said, the law of large numbers. We have many public PLG businesses now that are at billions of revenue. When you're trying to keep billions of dollars of revenue growing at a compelling rate, there's just only so far you can get on credit card swipes. You start having to take down much larger deals in order to keep the thing going in the right direction. So it is an inevitability, and it's easy though to look at it as something that might be simple. Well, just add enterprise. We'll add a new motion. But as you're pointing to, it's easier said than done. There's a lot that goes into it, and there's a lot of complexity with this one to many across a number of different vectors. What specifically makes that challenging? What does it break in the organization when you try to add this new motion?

Annie Pearl: Yeah. I think there's three main components in every organization that get impacted when you start to add this complexity everywhere across the business. The first is around people. We just talked about potentially building up brand new departments, scaling the existing departments that exist. Many times, the folks you have in the existing departments need to either acquire new skills, or you need to start bringing in a different skill set or experts with more specialized skills. There's this change in terms of the people required to get the job done, whether that's new departments or whether that's within existing departments. The skill sets and the experiences that you need with the folks around the table to be successful. So there's a people component. The second is process. In a just PLG world in many ways, organizations can... Different departments within organizations can operate in silos, and they can have their task and get their job done. There isn't necessarily need to be a ton of cross functional integration of plans or collaboration. When you move to not just having a product- led growth motion but layering on top of that a sales- led motion, this complexity requires that there's tight integration between the product roadmap, the marketing roadmap, the sales team plan for the year, or the customer success team hiring plan. You really have to make sure that the processes tighten up within an organization to ensure that there's a lot of integration. Then the last is on the product side. I touched on this in the beginning a little bit, but you really have to start thinking about new personas with very different needs. You need to start thinking about supporting more sophisticated use cases and balancing that against the simplicity with which your product probably went to market in just PLG world. Then also you have to think about a product led growth motion as a lead gen mechanism to your growing sales team. Across people process and product, just the exponential nature of the complexity with which you need to invest and integrate across teams to make this transition can cause chaos if not done with a lot of intentionality.

Blake Bartlett: So in short, it kind of breaks everything because when it's people, process, and product, that basically covers as much as-

Annie Pearl: That's your company.

Blake Bartlett: ... everything in thecompany. Yep. So going to the enterprise, do not do it in an unadvised manner. It is very serious. It breaks everything. If we look through those three lenses, people, process, and product, I know you've seen this transition done successfully multiple times. In your experience and from your view, let's start with people perhaps. How do you tackle the PLG plus enterprise transition in terms of people?

Annie Pearl: Yeah. As I mentioned before, a little bit of a mix of new roles as well as expansion of the talent profile or the skill sets you need in existing teams. I'll break it down first thinking about the product team. Typically, product- led growth companies tend to be made up of folks on the product team who have experience in more consumer product management, maybe growth product management, and all of a sudden, now you need to start thinking about bringing in talent who has experience building for the enterprise. Product managers who have experience building for the admin persona, thinking about the needs of IT in terms of security and compliance and more robust recording mechanisms. Going from more consumer skill sets to bringing in folks who have more experience directly building products for the enterprise is one piece of it. The second is then the evolution of the talent you have in seat. You have to really think about the product and the way you're building your product through the lens of not just the end user anymore, but also, what does this mean for the larger organization that I'm building for? You can get away with a lot more when you're just building a consumer product in terms of A/ B testing and experimentation. When you have IT who's purchased this for an organization, there is a expectation that the way in which end users use the produce, oftentimes it's very integrated in their daily workflows, that you're not just going to make changes willy nilly to the product that may impact the end users. So you have to really educate those who are in seat to understand how the work that they're doing for end users ultimately has to be thought through the lens of not just that end user, but also the larger organization that they're working for. That's on the product side. On the go-to-market team, as I already mentioned, spinning up new functions, you need to be really clear on what the ideal talent profile is that you're going to search for. As you're beginning this journey bringing in your first set of sales reps or sales leaders, you likely aren't going to want to hire someone or a team full of reps who've only worked in more traditional enterprise led companies where there's high- touch selling, there's longer sales cycles and really expectations around customization of the product to close large deals, if that's at odds with where you are in your journey. Making sure that you're hiring the reps and the sales leadership who understands where you are in your maturity model and isn't expecting the same level of product customization and way you go to market when you're chasing after really, really large deals. That's really important and helps with some of the tension that you often see between sales teams or go- to- market teams and product teams when there's misalignment around that. Which leads me to the third piece, which is just executive level alignment in terms of people of how are you going to win in the enterprise? Are you going to be chasing large deals? Are you going to be building what enterprises want if it sacrifices the end user experience? Are you going to say no to product requests that lose deals but allow you to maintain simplicity in your product? The more alignment you can get at the executive level, the better you'll set your teams up for success in terms of expectations around who you hire, what the talent is you're trying to bring on the teams, and how teams collaborate.

Blake Bartlett: There's a lot in there to unpack. One thing that initially stands out to me is that, first and foremost, you need to think about the skills, the additional skills that you don't currently have on your team. The capabilities, the competencies, the backgrounds, the experiences on product, on go- to- market, that you need to bring in and supplement. However, you also, it's not just a, we need this type of a person. Go get them, and then they're going to know what to do. There's a lot of context that's needed. You kind of mentioned understanding where the company is today. Where the product is today in its journey so that you don't just come in and brute force, copy paste a playbook onto an existing model, but you do it in the right way. It's both the skills, but it's also this context piece that sounds incredibly important.

Annie Pearl: Yeah, and I think it's even as tactical as terminology, and as tactical as what our approach is to selling into the enterprise. Are we really trying to go sell into CIOs as our first step? Or are we starting with department heads and then moving to centralized IT, and then thinking about a motion where we have more of a CIO level buy? So I think that alignment starts at the executive level, cascading down to the company around the approach to how we're going to go on that journey and ultimately win. Really dictates a lot of the people related, both skills that we're looking for when we're hiring, as well as training of folks who are in seat to be able to align to that.

Blake Bartlett: Yeah, that's kind of the alignment piece that you mentioned. The executive level alignment. Because there's more than one way to embrace the enterprise. Like you said, are you going to go to the C level? Are you going to go to IT? Are you going to go bottoms up still and come up through the organization? There are different ways to tackle it. Are you trying to take down the entire enterprise account from day one, or are we going to do more of a land and expand? Getting on the same page with that and having the alignment, and then using the same terminology, talking about the strategy in a consistent way, all of that's super important. Which really starts to point to that this is not just, again, filling roles and adding competencies. That's important, but there's really this massive cultural shift that happens when you take this this step.

Annie Pearl: Yeah, the second area or process is also another way of talking about culture. Everything prior to... In a world where you're just focused on PLG, again, you have the ability to have teams operating many times in siloed ways. As you start to think about moving into the enterprise, you have now these highly cross functional dependencies. And so you need to make sure that you're... The way you do planning changes, so that there's clear company goals that encapsulate both PLG revenue or ARR, as well as sales led. You need then cross functional OKRs or whatever planning mechanism you do that support both those channels. Then all the way down to the team level, individual team road maps across product, across sales, across marketing, across CX. They all need to layer up into these highly cross functional OKRs that are going to be in support of both product- led growth and sales- led growth. That's a pretty big shift from a overarching planning process that happens at companies. In addition to that, I think you also see the need for new feedback loops. Most of the time in a more of a PLG world, you can get all of your product feedback either in product or through reaching out to end users who are using the product and getting more qualitative feedback as well as quantitative feedback in terms of how people are using the product. When you move up market or you start to have this sales led model, you need much more tighter feedback loops from the admin, from the buyer of the organization, from the department lead, and make sure that that customer feedback's coming into product, as well as that product is doing a good job really getting feedback in terms of what's been launched and making iteration to what's been launched to make sure it's actually meeting the needs of larger and larger customers. So there's a whole bucket of work to think about new feedback loops and processes to ensure you're building the right things to solve the right problems for your customers that are ultimately going to make them successful with your product. Then I think the last thing on process is communication, and the need for communication between product and the rest of the company exponentially goes up in value when you layer on top of the product- led growth motion a sales- led growth model. That's everything from product roadmap, what's coming down the pipeline. It's giving advanced warning around things like product changes. It's product launches become much more cross functional in nature. They have a lot more dependencies, and they need to be a lot more tightly coordinated. There's a lot of things around communication as well that folds into the need for more process or adaptation of your processes as you're moving up market.

Blake Bartlett: This idea of going... It's going from single variable or single factor optimization to multi- variate and lots of complexity, as we've been talking about. But what that looks like in practice is, you kind of have to unlearn some of the ways that you've gotten to this point of being successful today. You have to unlearn some of the things that you've relied upon and some of those muscles that you developed, some of those cultural tenets. This idea of having a single factor or single variable that you're solving for, in the case of PLG a lot of times, it's the end user, as we've been talking about. What can we do to make the end user's life easier? What things can we do to deliver surprising delight to the end user? Then if you also then have a more startup- ey, earlier stage orientation towards speed... You know, move fast and iterate, just get it out there. If you combine those two things but you're going to the enterprise, you can actually shoot yourself in the foot. So needing to think about those multiple variables, multiple factors, and then not necessarily just orient towards speed and fast optimization, but instead taking a step back... Actually going slow to go fast is what it sounds like to me, in a lot of ways.

Annie Pearl: Yep. I think there's also philosophical alignment that needs to happen on the product side around what are you willing to and what are you not willing to do as you layer on the complexity? You could make the call that, at the end of the day, the north start for the company is maintaining simplicity of the end user experience, and we are not going to make sacrifices to the end user experience in service of the needs of large customers and unlocking deals. We can make that call, but then you have to make sure that's very well communicated, that's very well understood, and that you're going to maniacally focus on it. Alternatively, you can make a philosophical call around how you'll start to add in the... support the needs of larger customers, bring more complexity into the product. Sometimes, that may be at the cost of the end user experience, but in totality, this is going to be better for all customers and better for the business overall. You have a philosophical conversation around how do you want to approach the product going forward as you're layering in some of this complexity in terms of personas that you need to be able to solve problems for, and oftentimes the needs of the buyer can be at odds with the simplicity, maintaining the simplicity of the user experience. That's a big piece on the product side as well. I also already mentioned the notion of A/ B testing, experimentation. There's a lot more tolerance for that in just a PLG world. As you start to have paying customers and enterprises using your product, where there's built into their daily workflows, they are using your product, you can not just willy nilly run an A/ B test and impact the end user experience without advanced warning. That's another way in which the way you have to think about your product needs to change. You need to figure out, how do I still experiment and get the advantages of experimentation, while at the same time making sure that we're doing what we need to support the predictability of the product for large customers.

Blake Bartlett: Then I know that there are some fundamental trade- offs in embracing enterprise products from a starting point of simple PLG, if you will, which is that you, in the early days of PLG, you do want to make things as simple as possible, as easy to get started, as easy to get value. Strip away all of the excess stuff. How can we remove friction and just get you to that aha moment as fast as possible? That's a beautiful orientation. However, as you go to the enterprise, and you serve larger organizations, different industries, more use cases, you need to add more functionality. The product basically becomes less simple. It becomes more complex. How do you think about that trade- off of you have to become complex, but you don't want to become so complex that you lose your original way of the beauty and simplicity of why people love you in the first place? How do you manage that trade- off?

Annie Pearl: Yeah, I think there's two pieces, as I said. The first is really more around prioritization. What happens is you go from just the PLG to adding on a sales- led model as well, is you're going to have this prioritization tension between the two, just from a pure resourcing perspective. So I think the way to really help with that is having a very clear product strategy and alignment around where you are going to play, how you're going to win, and therefore, what the capabilities are that you need to build in order to be able to win. If you have alignment around that, then the prioritization between what are we going to be building for end users versus what are we going to be building for the department head versus what are we going to be building for the admin? They all are in service of the markets you're trying to play in or the areas you're trying to play in and your strategy for how you're going to win. It really starts with having a clear product strategy and letting that guide a lot of the decision making around prioritization between what can be this tension between, do I work on something for the end user? Do I work on something for the admin? As I'm thinking on working on something for the end user, do I keep it as simple as possible, or do I do it in a way that's going to really solve for the needs of the larger organization? I think getting a really clear product strategy is one way to help with a lot of the prioritization challenges that comes with supporting both of these funnels. Then I think the second is using things like product principles and design principles to really be your guiding light in the execution of how you add in features and functionalities that are aligned with your product strategy, but doing so in a way that maintains the simplicity of user experience or what got you here and made you so successful to date. I think you can use product principles and design principles to really help more at the tactical level as you're then developing the features that you've decided are part of your longer term product strategy for how you'll grow both the product-led growth funnel, as well as support larger and larger customers through a direct sales motion.

Blake Bartlett: The other thing that I've seen here is the ability to bridge that gap through solutions as well. Through solutions, both in terms of how do you package up features, both from a product standpoint, from a product marketing standpoint and a messaging standpoint to go after individual industries or use cases or needs, while still maintaining at the atomic level the simplicity for the end user, if you will. A great example that comes to my mind is LinkedIn. If you use LinkedIn as an individual person who signs up and creates a profile and networks on it, it's kind of been the same way that it's always been. They've added some more capabilities. The network has gotten stronger. There's all this content stuff going on, but it still is the same fundamental thing. But then the stuff they sell to the enterprise is a talent solution, a recruiting solution, a sales solution, an advertising solution. Adding that complexity and orienting towards that solutions doesn't actually affect you as just somebody who's on the network, but it does add that value, and it does give them that ability. Have you seen this solutions piece be important in this transition?

Annie Pearl: Absolutely. You touched on one version of it, which is we can create new products within an organization for other personas within that organization that doesn't necessarily need to be built into the horizontal product that we built for the average user within an organization. Calendly, for example, where I work, we think about different personas and different departments within organization. We serve sales, we serve recruiting, we serve customer success teams really, really well in terms of helping them better schedule externally. As we think about building products for those personas, we have opportunities to create distinct and different experiences for those audiences that aren't necessarily available or don't impact the more horizontal scheduling product that's used more broadly across any persona in any organization. I think you have the opportunity to build specific solutions for personas within organizations in a separate UI and a separate skew, leveraging horizontal capabilities that you have on a platform, but you can go intentionally build for more purpose- built experiences for different personas without having to try and shove that all into one horizontal UI. Definitely seen that as one way of more solution- oriented ways to solve the needs of a specific persona in a more in depth way without building that complexity into the horizontal platform. The other thing is just taking more of a platform approach as well, creating a more customizable product that can be customized for a specific departmental need through more of a platform approach as another way to do it as well. Creating more of an open platform where you could actually do custom development for a specific user that, again, doesn't need to be built into the horizontal product that is impacting every single user, but you can actually spin up new experiences for those personas.

Blake Bartlett: What I'm hearing through that in this discussion around solutions is that solutions, when done right, gives the customer the ability to opt into complexity without overwhelming them from the beginning. You can still start the journey the same way. You can still use the basic use case, get the initial basic straightforward value, but then as you continue on your journey, you can kind of... It's choose your own adventure. You want to go down this path and get some more value in this direction? Great. We'll help you in that direction, but we're not going to overwhelm you with it out of the gates unless you ask for it. That ability to progressively introduce more complexity and more options and more solutions to deliver more value as somebody goes through their journey. It's a way to maybe get away from the, it's got to be all or nothing right out of the gates orientation that some folks can have when they go towards the enterprise.

Annie Pearl: That's right. I think it also easier to come at that if you start it off as more of a horizontal platform, and you then can sort of go deeper in certain areas and spin off solutions for different personas. It's a lot easier to go from that angle than starting with specific personas and building purpose- built deep products for those personas and then trying to move into new personas or more into more of a horizontal product. Some of it also starts with, and you see this in a lot of PLG companies, they start with pretty horizontal products in nature, and then they see adoption in different parts of organizations that then lead them to say, " Oh, here we have incredible product market fit within these three departments. We're going to start to build some more in- depth functionality for those users," which then allows them, that's a jumping off point to go potentially build a different product experience for that user that doesn't have to impact the more horizontal nature of the product that they originally came to market with.

Blake Bartlett: I like the other piece that you mentioned around the platform opportunity. It's even another layer of the ability to opt into complexity. Because at some point, you do have to draw the line. You're not going to build everything that can be built, even if there is value, and so there is a point at which you can do a hand off to your partners or to your developers or to integrations and things like that. The choose your own adventure of complexity and what you can opt into can keep going and going and going. Some people have incredibly complex and sophisticated Slack instances with every integration you can imagine and all this stuff wired up. It really has become their work OS. But some people just still use it for basic chat, and that opportunity through platform and extensibility is another really important layer to consider.

Annie Pearl: Yeah and I think as you-

Blake Bartlett: We've talked about a lot of stuff today. Oh, sorry. Go ahead.

Annie Pearl: No, no. No, I was just going to say, I think one of the great things that has happened as well over the last decade is this consumerization of IT and the investment in organizations into productivity technology and moving to the cloud... It has been an increase in resources internally in organizations, especially large organizations, to be able to create and build customized experience for end users to make the most productive. So the platforms that have been built through the lens of being API first and thinking about wanting to enable organizations to build custom experiences to meet their needs, it's this perfect storm to taking away a lot of the lift that would historically have been put on technology companies to have to build lots of customizable solutions themselves. They can really offer it up as a platform, choose your own adventure, let the organization really build more of a purpose filled version of your product for their employees to make them most productive based on their use cases.

Blake Bartlett: In closing, for any PLG company that's on the cusp of this transition, they feel the pull, or they want to make the step towards enterprise, where should they initially focus? I know we've talked about a lot of stuff today. What do you think is foundational step number one?

Annie Pearl: Yeah, I think summarizing a lot of what we talked about, which is what happens when you make the transition? What are the biggest challenges that you want to get ahead of? I think you kind of take a step back. The most important first step is getting alignment, starting at the executive level, and then trickling that down into the company around what your approach is going to be towards this transition. It's really answering two questions. On the product side, it's what is our philosophy around how we want to evolve this product to meet the needs of larger and larger customers as it relates to balancing the end user and the needs of IT and the admins of an organization? There's a philosophical product question that needs to be answered. Then on go- to- market side, what are the types of go- to- market teams that you're looking to build up? And therefore, what type of talent and experience and skill set and expectations do you want to build into the team that you're spinning up in order to marry that with the product philosophy and ultimately be successful as a whole organization? If you can't get alignment on those two questions, what's the product philosophy and what's the type of go- to- market team that you're looking to build, I think you're going to set the company up for really failure because everything from the people you hire to the processes you put in place to the product decisions you make may not... Will be at odds potentially with either one department thinking the other department isn't doing what they need to make them successful. Ultimately, you'll slow down. You won't move nearly as quickly, and you won't accomplish the goals that you have as an organization. I actually think the most fundamental first step is alignment and getting alignment around what your approach is, how you're going to win as you make this transition, and then setting those expectations with the product team, with the go- to- market teams that are going to enable them to work collaboratively in service of a very aligned around strategy for how you're going to win as you move up market.

Blake Bartlett: What I'm hearing from that is that patience is really important and crawl, walk, run. Don't try to skip steps. Because I do think a lot of times, folks just want to do things. They want to make progress. They want to feel like they are doing the enterprise thing. Let's get that enterprise sales leader. Let's get that seat filled, and let's get going as fast as possible. Or let's build that feature. But you can actually get ahead of yourself and get over your skis if you do that, if you hadn't planned and had a great strategic direction. So you kind of have to, as you were saying, you have to decide, what do we want to be when we grow up? When we grow up to be an enterprise company, what do we want to be? What are we not going to be? Let's get really clear on the strategy. Once we have that, then we can start taking action. But don't put the cart before the horse.

Annie Pearl: You got it.

Blake Bartlett: Awesome. Well, Annie, this has been an incredibly helpful conversation for me and I know for everyone listening right now in terms of how to make this inevitable transition that every PLG company faces, so thank you for walking us through your experience and your wisdom. This has been great.

Annie Pearl: Absolutely. Thanks for having me. This was a blast.

Blake Bartlett: Thanks for checking out BUILT. If you enjoyed the conversation today, make sure to subscribe on your favorite podcast platform. Leave us a review, so that others can find the show as well.