20Product: Calendly CPO Annie Pearl on Why All PLG Companies Eventually Need to Embrace Enterprise, Why it is Easier to Scale into Enterprise than Visa Versa and the Calendly PLG Playbook; What Works and What Does Not?

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. The company now has over 10M users around the world and over 50,000 companies loving the product. As for Annie, before Calendly, Annie led Glassdoor's product vision and user experience, managing a 70 person product and design org. Prior to Glassdoor, Annie led enterprise product teams at Box both before and after their 2015 IPO. If this was not enough, Annie is also on the Board of WorkRamp and Well Health. In Today's Episode with Annie Pearl We Discuss: 1.) Entry into Product From Consulting: How did Annie make her way into the world of product and come to lead product teams at Box and GlassDoor? What are 1-2 of her biggest takeaways from her time at Box and GlassDoor? How did they impact her product mindset? What does Annie know now that she wishes she had known when she started in product? 2.) PLG vs Enterprise: What, When, How: Is it possible to do PLG and top-down enterprise strategy together from Day 1? Why does every PLG company eventually have to adopt an enterprise strategy? What are the single biggest challenges companies face when moving to enterprise? How do founders know when is the right time to make this transition? How do founders need to restructure their org to make the transition to enterprise? 3.) Building the Product Bench: Hiring: When is the right time to hire your first product leader? What are the core signals? What are the core character traits needed for a first product leader? How do we specifically structure the interview to test for them? Who do we bring into the interview process from other parts of the org? Do we do case studies with candidates? If so, how long do they have with the data? What is the difference between good vs great with case studies? 4.) Product Strategy, Reviews and Alignment: How does Annie assess how often product strategy should be reviewed? When should it change? How does Annie approach post-mortems? What is the right way to structure them? How does Annie create alignment between sales and product? Why is this so important? What is the single biggest product mistake Annie has made? What did she learn?

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  Welcome back to another very special 20 product episode. This is the monthly episode where we sit down with one of the leading product minds to discuss scaling both product and product teams, sharing their tips, tactics and experiences. And today I'm super excited to welcome Annie Pearl, CPO at Calendly, the company that makes scheduling meetings simple and painless. The company now has over 10 million users around the world and over 50,000 companies loving the product. As for Annie, before Calendly, she led Glassdoor's product vision and user experience, managing a 70% product and design org. And prior to Glassdoor, Annie led enterprise product teams at Box, both before and after their 2015 IPO. And if this wasn't enough, Annie's also on the board of WorkRamp and Wellhealth.

• 0:41Harry Stebbings?

  And a huge thank you to Ted Blosser at WorkRamp, Topi Calendly's CEO, and Adam Draper for some amazing question suggestions today, really did make such a difference. But before we dive into the show today, you have to check out builder.ai. They make building software so easy that anyone can do it. If you have a vision, you can build it with builder.ai. And one of my favorite products of theirs is Studio Rapid. I always think the number one reason people fail is they don't start. And Studio Rapid is the perfect tool for when you need an MVP fast. And when I say fast, you can build simple, beautiful native apps in less than one day. But don't just take my word for it, take the words of BBC, Pepsi, Fujitsu, some of the world's leading brands, all loving and using the builder.ai product suite.

• 1:26Harry Stebbings?

  Head over to builder.ai to find out more. And speaking of creating beautiful customer experiences and products, if your business runs on a mobile app, you have to check out UXCam, designed specifically for mobile product teams. UXCam helps build better apps by making user motivations and frustrations loud and clear. Product teams love this app experience analytics platform that empowers them with clarity and speed. UXCam auto captures billions of micro-interaction level data like screen swipes and taps, with tools like session replay, heat maps, funnels, crash analytics, and auto capture of user frustrations and bugs. It has never been easier to uncover real user behavior. Join over 30,000 apps, such as Costa Coffee, Nando's, Delivery Hero and Rappi, who optimize their product with UXCam.

• 2:11Harry Stebbings?

  If you're not using UXCam, what are you waiting for? Go to uxcam.com/20vc to claim your free two-month extended free trial. But I'm now so thrilled to hand over to Annie Pearl, CPO at Calendly.

• 2:30Speaker 01

  You have now arrived at your destination.

• 2:33Harry Stebbings?

  Annie, I'm so excited for the show today. I've heard so many great things. It was Vanessa at NEA and then many, many more and many more help with the schedule. So this wasn't really my work at all. But thank you so much for joining me today, Annie.

• 2:44Speaker 03

  Thank you so much for having me, Harry. Super excited to be here.

• 2:47Harry Stebbings?

  So you've led some of the most fantastic product orgs recently with Calendly. So how did you get into the world of startups? And then how did you come to Calendly in a very swift two to three minutes?

• 2:56Speaker 03

  Yeah, absolutely. So I started my career off actually intending to be a lawyer. And while I was in law school, I actually worked for a management consulting firm and we specialized in working with startups. So I was in law school, assuming I would be a lawyer, but I was getting much more interested in technology and sort of the idea of building companies and products. So after passing the California bar in 2009, with the intention of being a lawyer, I ended up actually joining the founding team of a startup called Expert Financial. After raising venture capital money, we hired a bunch of engineers and designers and I took the role of leading products. So that's really how I got into product management. In my time at Expert, we very much zero to one. How do you get a product off the ground? How do you find product market fit? All the peaks and valleys of kind of early stage startup life. I think that experience really taught me about sort of the power of focus, especially

• 3:39Speaker 03

  in the early days of finding product market fit, just how important it is to kind of maniacally focus on solving one problem and solving it better than any alternative on the market.

• 3:47Harry Stebbings?

  Super quickly, otherwise I forget. When you get to my memory is terrible.

• 3:50Speaker 03

  Of course.

• 3:51Harry Stebbings?

  One problem, I agree. What's the framework for deciding what that one problem is? And does that change over time, what you focus on?

• 4:00Speaker 03

  Yeah, I think at the beginning, you really want to focus on finding where's the sort of most acute visceral pain points that someone might have within some sort of problem space or some sort of market. I may feel really narrow at the beginning, but I think the mistake that early stage founders make, the shiny objects. We came in saying we have this really acute pain point around private market liquidity. But then we said, well, let's also do a capital raising platform. Oh, and let's also build a data room. Oh, and let's also build a way for, you know, connections to be made in a networking platform, right? And so as opposed to just sort of narrowly sticking to this acute pain that we knew sort of was being felt in the market, we decided to build new products far too soon. And I think that's probably my biggest lesson from that experience.

• 4:39Harry Stebbings?

  How do you know when's the right time to do a second product?

• 4:42Speaker 03

  Yeah, I think you get to a place with your first product where it's very clear that you found product market fit, right? Your target customers are actually using and buying and talking about your product. There's a lot of definitions out there of what product market fit is. I think that when you see it, you feel it and you know it's there. And I think you have to be really diligent of, even once you've found product market fit, really doubling down and scaling the existing product for quite some time period. And then you sort of get to a place where, okay, things are pretty repeatable, things are pretty predictable, growth is something that we can really model out. Now let's actually start to think about what the next product is to build. And I think actually maybe one of the bigger mistakes that companies make is doing that too late. And so they stay on their current product and they don't actually know how long it's going to really take to build a brand new product, to actually get it to market, to finally see impact in the business.

• 5:27Speaker 03

  And so they find themselves behind the eight ball, having not actually invested early enough, or at least laid the foundation for what they might want to do as their second product.

• 5:35Harry Stebbings?

  Does the second product always have to have direct tie back to the first product? Like, do they have to be completely adjacently provided or aligned?

• 5:42Speaker 03

  I don't think they have to. I think that it increases the likelihood that you'll be able to do it faster and that you'll be able to deliver additional value to the same set of users if you do. And I think oftentimes you sort of think about the second product as you have an advantage because of the first, right? You have a distribution advantage, you have a data advantage, you have something that you're taking advantage of. And so I think usually they happen to be pretty well tied together. I don't think it has to be the case, but more often than not, I think there's a reason your second product relies on your first product to become successful.

• 6:13Harry Stebbings?

  I used to be such a little timid interviewer, but I was like eighteen when I started. And I've got more sassy over time, I think would be the same. When you look at Calendly, you have such strong brand recognition within a certain market and within a certain, like, specific function. Is there a second product? And if so, it's not so well known, obviously, because it's so dominant within. And if not, have you not waited too long?

• 6:35Speaker 03

  It's a great question. So I think about Calendly as our history and where we've come to date. We really started off as this very horizontal scheduling automation platform, right? Allowing whether you're a solopreneur, you're a lawyer, a real estate agent, or you own a nail salon, all the way to To a sales rep in an organization or a customer success rep in an organization. The breadth of use case was very broad in terms of who we serve. And that really represented what we call kind of horizon one or the first act of Calendly. And that's really we grabbed a lot of market share and became kind of ubiquitous. What we're actually transitioning to now and have been for quite some time is going deeper into these sort of use cases where you have really strong product market fit. So our customers have pulled us into externally facing roles within organizations. So that's the phase we're in today, going deeper there.

• 7:20Speaker 03

  The third phase where I think we'll go eventually is beyond that and to really trying to own and help support and deliver on the entire meeting lifecycle. So scheduling is really just a wedge into a much broader meeting lifecycle. It's everything before the meeting, during the meeting, after the meeting. And there's really no one out there orchestrating some of the most important interactions you have with your customers around meeting management.

• 7:41Harry Stebbings?

  On the verticalization side, and when you look at the different requirements from each, they are very different, whether it's sales, marketing, CS, or whatever we're catering to within these different functional areas. My question to you is, does that not turn a very product-led growth organization into a verticalized sales approach dependent on the function that you're selling into? And how does the org change with product-led growth, chapter one, to verticalize use cases, number two?

• 8:06Speaker 03

  So I would say this is the beauty of starting off horizontally and then going vertically versus trying to start off vertically and then going horizontally. So when you think about starting off horizontally, eighty percent of the functionality we have today will solve the use cases of those departmental users. And then there's some functionality that very specifically is for the departmental users, but actually crosses across departments. So as you think about meeting scenarios where you have multiple individuals within an organization, it might be a sales rep and an SDR, it might be a hiring manager and a recruiter. And you've got multiple individuals in an organization who need to schedule time with someone externally. We can use that same functionality to support multiple verticals. So you get a lot of benefit from starting horizontal, call it eighty percent. And then when you go vertical, you try really hard to say, what are the things we can go build

• 8:51Speaker 03

  that are actually going to solve for problems across multiple of these departments? And we draw a line, right? We say, at the end of the day, we're not looking to be a point solution just for Sales reps. And so if there are things that are going to be too narrowly focused on that audience, we sort of have to make a judgment call around whether we're going to go do it or not.

• 9:06Harry Stebbings?

  It's a really interesting strategic question of like, what's big enough and what's attractive enough. My question that I have, and you said it fantastically well before, and I love this, and so I have to pick up on it, which follows from this, which is every product like Growth Company eventually has to embrace the enterprise. Why?

• 9:22Speaker 03

  Yeah. So, you know, I think there's a couple of different reasons for this. I think the first one is the sort of PLG motion, which, you know, in a lot of ways is really just a self-service motion, can get you into the several hundreds of millions of dollars in revenue scale. But typically, the ACV is really low, the account value of those users. And so just love sort of large numbers makes it hard to sustain kind of high year-over-year growth rates when you reach that triple-digit million revenue scale. I think you also oftentimes hit sort of a market size limitation of just solo users who can kind of pull out a credit card and buy your product. So the first is you sort of growth of the PLG channel naturally slows at some point, once you get into sort of hundreds of millions of dollars in ARR. I think the second thing is then you sort of have to think about the pursuit of expansion

• 10:04Speaker 03

  opportunities. And while you can do some of that online, going from a solo user to a small team, if you're really trying to go to medium-sized or large teams or multiple departments in an organization, that's going to be a conversation with a buyer, right? That's going to be more of a top-down sale. And then lastly, I'd just say, almost all PLG businesses, the goal is to get as many people in the organization using your product as possible. And we kind of call wall-to-wall deployments. And to do that, you sort of have to engage with not just the department heads, but actually kind of your IT buyer, the ultimate decision-maker around standardization of tools across an organization. So you see every iconic PLG company, whether it's Slack, or Dropbox, or Asana, or Zoom, you know, at some point, they have to add on that sort of direct selling motion to complement the PLG business.

• 10:47Harry Stebbings?

  My, my big worry is I see so many founders move into enterprise too early. There are like 2 million in ARR, and they're going, we're going to layer on enterprise. It's very wide. And so my question to you would be, when is the right time, do you think, to move into enterprise? And what are signals that actually you should go there? Because often they'll pull you there. Should you just listen and go? Or is there a right signal?

• 11:09Speaker 03

  Yeah, I think you nailed it, which is going too early can be detrimental, right? Hiring a bunch of sales rep when there isn't demand creates a bunch of noise. It creates extra costs for the organization and ultimately, you know, those reps aren't going to be successful. So, you know, definitely want to be very careful around making sure you're timing it right. One of the pulling mechanisms you see really is in usage data. And so, Calendly, what we started to see was these core ICPs, sales, recruiting, our customer experiences teams within organizations, starting to become some level of mass, right? Fifty sales reps within an org, a hundred sales reps into an org. And you sort of start to see this pattern emerging across all the organizations that use Calendly to say, we've sort of hit a threshold where if we were to go have a conversation

• 11:52Speaker 03

  with someone internally, there's enough mass here that that conversation would be productive and there's a likelihood that they would actually want to standardize Calendly on Calendly beyond just the department or the subset of users that are using it today. So I think you have to use the data to really help inform, are you ready? Maybe even a more important question is, are you ready organizationally? And that's probably one of the biggest challenges I see when people start to move up and layer on a sales team.

• 12:16Harry Stebbings?

  Well, let's talk about that. From the organization perspective, what are the biggest changes that you need to make when moving from PLG to enterprise?

• 12:23Speaker 03

  At the highest level, there's just an increased complexity that sort of happens across the whole organization, right? For the product org, you're going from serving sort of individuals to teams of users to departmental admins to the IT buyer. You know, you no longer get to just maniacally think about this end user. On the sales side, maybe you went from no sales team to building one from scratch or from an inbound motion mostly to an outbound motion. Similarly, on the CX side, right? Mostly reactionary support to how do I have now like a managed accounts team that's working with our large customers? So everywhere across the organization, you're sort of getting complexity within those departments. The second thing that happens, not just within each department, but is in across departments. And so all of a sudden now, you have these dependencies popping up everywhere, right?

• 13:06Speaker 03

  Product can no longer just go build an A/B test and release things for end users. They have to think about how do I involve sales? How do I make sure sales knows? How do I know that I make sure our CS team knows? So a really big integration between product and the go-to-market teams and integration between, you know, the demand gen teams and the sales team, the sales and CS team. So all of a sudden, you've got like many more dependencies across the entire organization. And then I think the last piece is you now as an organization have multiple priorities. And again, it's no longer just PLG and the funnel and optimization of an online funnel, but you've got both of these motions. And so at all times, there's going to be questions around which is more important. Should we be investing in this one over that one? So I think just across all those dynamics, it becomes just a lot more complex in nature.

• 13:51Speaker 03

  And if you're not prepared for that, it likely won't be very successful.

• 13:54Harry Stebbings?

  Can I ask, for you as CPO, does this not suck? Like you go from like customer delight, you know, doing product roadmaps on like incredible like workflow designs to like, I mean, what people forget is SSO, R back, security enhancements, everything that comes with it. This sounds awful. Why would you do that as a product person? And from the product perspective, not an org perspective, what needs to really change?

• 14:20Speaker 03

  I think there's two answers to that question. The first is you're absolutely right. There's blocking and tackling you have to do from a security and compliance and sort of scale perspective to help support larger and larger customers. That's just sort of work you have to do. I think the more interesting work potentially is that as you think about these larger organizations, you think about the dynamics in them, you're actually now going from a simple use case of I just need to think about this one solo user to potentially a team of users and then potentially a team of users working with a team of users. So from a product perspective, that's actually really, really interesting. You know, you have to think about how do I create value across departments in an organization who maybe don't ever talk to each other except for this product? How do I think about going deeper and helping to solve the needs for, again, this recruiter

• 15:05Speaker 03

  in a way that's also going to unlock this use case within the sales department? So I actually think from a product perspective, it becomes more dynamic and actually really more interesting, even though yes, there is the blocking and tackling you just have to do in order to be able to sell into the enterprise.

• 15:17Harry Stebbings?

  What are the single biggest challenges for you as you layer on enterprise onto a very successful PLG motion? What has been the biggest challenge?

• 15:25Speaker 03

  I think for me and what you typically see is the prioritization. And I think this really starts with making sure there's incredible alignment at the executive level around how do we think about these two motions coming together to serve the overall needs of the business? Are we okay, for example, with slower growth in sort of the PLG business for some time period while we're investing in growing the sales business? Are we okay with just overall the sales business not growing nearly as fast? Because we want to continue to grow at really high rates of PLG. So I think the most important and the biggest challenge that organizations face is not having that alignment at the executive level. And then so the folks on the ground don't know, am I supposed to be working on a feature in service of, you know, the self-service buyer? Am I supposed to be thinking about a departmental use case?

• 16:07Speaker 03

  Am I supposed to be thinking about, right, meeting the needs of the security and IT buyer? And so I think it all starts with that executive level alignment.

• 16:14Harry Stebbings?

  Can you do PLG and enterprise from day one?

• 16:17Speaker 03

  It's a very good question. I don't know that you need to. The beauty of the PLG business is that it enables you to build a highly profitable engine that in theory should allow you to, you know, with incredible unit economics, in theory it should allow you to almost kind of bootstrap the business to get the opportunity to then go invest in sales and marketing dollars to unlock the larger deals. So the beauty of the business model is it's much cheaper. You require way, way fewer resources. And if the product sells itself and markets itself, then you really don't need to build out sales teams and marketing teams until you're really ready. So I think the ideal approach is if you can find a way to build PLG from the bottoms up, from the beginning, you're able to unlock a much more efficient business,

• 17:02Speaker 03

  which allows you to then sort of be in charge of your future and decide, when do I want to go actually take some of this money and invest it in sales and marketing and move up market? It's much harder to scale down than it is to scale up. And when I was at Glassdoor, I had the opportunity to build our self-service business from the ground up. And when I joined, we were very much a enterprise-focused business. We had a huge direct sales team. We were very successful and sort of mid-market and enterprise customers. And we wanted to build a self-service product from the grounds up. And so the challenge with that is when you have a direct selling motion already, you can't. And come into some challenges around rules of engagement as it relates to the channels. We had this experience that we built this self-service product. It was starting to do well.

• 17:43Speaker 03

  And so you'd have a customer sign up online, post a couple of jobs and one day later a sales rep reaches out to them and says, hey, I want to upsell you. And that's a really terrible customer experience. And so I think it's actually a lot easier to nail the sort of bottoms up motion first and layer on top of that. More of a direct selling motion, I think, than it is to come down market.

• 18:02Harry Stebbings?

  In a world of PLG, product marketing matters more than ever because you don't have the stabilizer of the sales rep. I think product marketing today is really, really shit. It's bland. It doesn't make you feel anything. When you think about great product marketing today, especially given that coming from PLG where you have a website to sell and that's it. What do you think great product marketing is?

• 18:22Speaker 03

  I think that great marketing of PLG products is not actually about product marketing. It's about the actual product itself. The product quote unquote marketing is I use the product. I introduce the product through the course of using the product to someone else who uses the product, who then gets value and then introduces the product to someone else. Of course, that's just one version of PLG, right? That's the viral loop of PLG. But to me, the essence of PLG is sort of quote unquote product marketing is using the product and getting value out of the product and therefore introducing the product to new people. And in fact, your sort of product marketing are the users versus a function within an organization. I think then as you start scaling and actually start moving out market, that's where the product marketing team really becomes much more embedded into the product org.

• 19:04Speaker 03

  Because now you're thinking about different audiences, you're thinking about positioning, you're thinking about the buyer and how do I think about introducing the product to different buyer segments? And the role of product marketing, I think, actually becomes much more important as you're thinking about moving up market versus the product. Marketing itself is most important when you're sort of just thinking about the PLG channel.

• 19:23Harry Stebbings?

  Speaking of kind of product marketing there and the definitions changing over time, product management is one which is just super loosely defined. And I always feel too naive to actually really ask what it actually is. How do you define product management and what does it mean to you?

• 19:37Speaker 03

  Yeah, to me, I think it's really boiled down to two main components. I think the first is prioritizing the right problems to solve. It's all about. We have limited resources and the job of a product manager is to make sure that you're working on the most impactful things for the business. So the first is prioritization of the problems that you're going to go solve. And then the second is being able to actually build winning solutions to those problems. And ultimately, your goal between both of these prioritization and execution is delivering impact to the business. So that's how I I define product management.

• 20:07Harry Stebbings?

  Is product art or science? How would you think about that?

• 20:10Speaker 03

  So as I think about that definition of product management, right? Prioritization of problem statements are the problems you're going to go after. And then being able to actually build a winning product solution. The science can be very well applied to that first part of that. In terms of identifying the biggest opportunities to go after, you've got quantitative data. You can understand how are people using the product today? Where do they have challenges when they're using it? Who are our most successful users and what does their user journey look like? So you can use a lot of data, both qualitative and quantitative, to really help you prioritize. What are the biggest opportunities or what are the problems we're going to go after? Science, therefore, I think is very heavily influencing that part of product management. When it comes to then, how do we build a winning product solution? This is where I think it becomes much more art.

• 20:51Speaker 03

  And there's this definition of of sort of quote unquote product sense that that we talk about a lot, which is just sort of this combination of curiosity and creativity and intuition around how to solve a problem. And that, to me, is something that's that's, of course, you can still use some science. You'll do discovery, you'll talk to customers, you'll get input. But at the end of the day, there's a lot more art to building the winning solution than I think there is science.

• 21:13Harry Stebbings?

  It's almost harder because you can't learn art like you can science. And so when we think about this discussion, so many founders listen to the show, and you're going to be a hypothetical angel in my company. Thrilled to have you. Thank you. My question to you is, I'm founder and CEO. When do I hire a CPO or a head of product? What are the signals that now is the right time?

• 21:32Speaker 03

  So what I typically see is you sort of the journey around when to bring in a product leader really, really corresponds to where a company is in their growth trajectory. Pre-product market fit, founders usually doing most of the product management, working with directly with the engineers, getting things built. Then usually, you know, you find product market fit and and maybe you bring on your first product manager or your first, you know, sort of quote unquote product leader. And really, the job is to continue. To execute on the founder's vision. And so you gotta be really clear that that's the job, right? The founder typically is the one who's really driving and your job is really to execute. And then when you sort of hit this like level of scale of things are working well, we're humming. Then your job as the product leader become not just executing the founder's vision, but how do I create predictability? How do I create repeatability?

• 22:14Speaker 03

  How do I start to hire team and start to make this machine move faster to continue to essentially execute? And then I think you hit another phase, which I'll just call kind of hypergrowth or late stage, where you have a product and it's humming and now it's time to open up new growth levers. So you're talking about new products, you're talking about new geographies, you're talking about new channels. And that's where you typically see someone bringing in a CPO, someone who's, you know, seen the movie play out before, hired great product teams, you know, able to work in a really complex environment. That's typically how you see the kind of trajectory.

• 22:47Harry Stebbings?

  Incredibly rogue forward suggestion. I've, I've seen different profiles from interviewing the best CPOs in the world. And there's like visionaries early, and I think Shreyas Doshi says this quite well, visionaries early, it really kind of foresee the future, crafts people who really kind of crafted in, in different ways. And then there's operators and the operators are good at process repeatability, but they're not very creative or artistic. And my question to you is, do you have to lose creativity and artistry? And the art with scale of product management of teams, do you know what I mean?

• 23:21Speaker 03

  Absolutely not. And the best product companies out there find a way not to. An important part of that formula is, one, what's the role of the founder? And this is where I think the relationship between the CPO and the CEO or the founder CEO becomes really critical at this stage that you're talking about. Because the mistakes that I see happen is that the CEO founder goes to hire for a skillset that is either at odds with what they really need, or they're not actually honest with themselves around the role that they want to continue to play within product. And so if you're, if you're a strong visionary founder CEO, really you just need an operator and an executor, but you go hire someone who's drawn on vision. Well, then you're just gonna clash or opposite, right? You really need someone who's gonna bring that vision, the founder.

• 24:05Speaker 03

  CEOs moved into a much different role, but you go higher at what you just described as sort of the operator. Well, yeah, you're going to start to lose that product culture and that that vision and that craft. So I think it really actually comes down to understanding the dynamics between the sort of what is typically a founder CEO and the CPO. And who has what strengths, how do those complement each other? And making sure there's incredible clarity around who's going to be doing what as it relates to product.

• 24:30Harry Stebbings?

  Well, I mean, I think a lot can probably maybe be corrected then in the hiring process. If you're able to identify the right people early enough, not to or to hire them. So when we think about the hiring process, again, I'm a young first time founder, but my company is fantastic. And you're an angel, so lucky you, but we need help on this hiring process for the product team. How do I literally structure a hiring process? How do you do it today? And what do you want to get out of each subsequent meeting?

• 24:55Speaker 03

  I think the most important part is starting first with what do you describe as the competencies with which you evaluate product managers? Or what you need out of product managers of your company. This varies company to company. And as we've already talked about, the definition of what product management is even something that is described differently by different product leaders. So I think most importantly, before you even start bringing anyone in through the door is getting onto a piece of paper. What are the core competencies that we believe are required out of every product manager here? Or very specifically, the role we're hiring for? And how are we going to test each of those competencies? And so once you sort of have at least a general framework for what you're looking for for candidates. And it typically goes through sort of a three part process. The first is usually the hiring manager phone screen.

• 25:36Speaker 03

  This is typically where you want to really understand more deeply their background and their experience and their skill set. And maybe even most importantly, their interest in the role. And if you can get ahead of wasting time across the whole interview process, just to find out that really this person's interests don't really align with the role. You'll save yourself time and you'll save all the folks on your team's time who have to go interview. So hiring manager phone screen first, assuming that goes well and the hiring manager feels confident that their experience and their skill sets are relevant. Then you typically will move on to the panel interview. And the panel interview will really be taking those core competencies and assigning them to each of the individuals on the panel. And having a very clear. And repeatable way with which you're teasing out whether someone has that sort of competency or not.

• 26:21Speaker 03

  The biggest mistakes that folks make on the hiring panel is there's not a lot of order and structure. And so you've got, you know, one person goes in and asks one question, the other person goes in and asks another question. Questions are actually like pretty similar and so you don't actually tease out anything new from each of the different steps of the panel.

• 26:36Harry Stebbings?

  Are there commonalities in the competencies that we look for? Again, I have no idea. So it's like, what are those if there are some commonalities?

• 26:44Speaker 03

  For me, I look at really kind of four main components of what I would expect out of a product manager. The first is really all about sort of synthesizing large amounts of information and data points and being able to use that to prioritize the right problems to solve. You might call that sort of strategy. The second bucket is can you then use your curiosity, your creativity, you know, your intuition to tell a compelling story around what a winning product solution might look like to that prioritized problem? And that's where we sort of talk about product sense. The third for me is can you then inspire and influence your team to deliver this winning solution that you've sort of come up with? And that's sort of the bucket there is leadership and communication and execution. And then lastly, can you sort of set up the right success metrics

• 27:27Speaker 03

  to ensure that you know whether you've actually made the impact to the business that you were expecting to? And if you didn't, are you sort of adaptable to testing and learning and iterating until you get it right? So I think those sort of strategy and product sense and leadership, communication, execution and analytical thinking tend to be sort of the different buckets that most product organizations are looking for in product managers.

• 27:48Harry Stebbings?

  The reason I was looking down is because I don't know if you can see, but I was writing on my arm.

• 27:54Speaker 03

  A lot of things.

• 27:55Harry Stebbings?

  I told you, my memory is not so great these days. So, okay, so we're testing for these competencies. Strategy, number one. Are you a strategic mind, Annie? How do I test for like strategy and that ability to be a strategic thinker within product?

• 28:09Speaker 03

  Yeah, I think the strategy question really comes down to how do you take, again, lots of different data points? How do you sort of synthesize those and come up with a essentially prioritization framework to help you make decisions? To me, sort of product strategy is all about. Identifying what do we need to do, sort of do and build in order to win within those markets? And then ultimately, what are the competencies or things we need to go build in order to win within those markets? So it's a series of decisions around ultimately what you need to go build, but it's all in service of how you're going to win within the market, the target market that you have identified for yourself. And so I think what you're looking for with strategy is how do I essentially create a framework for decision making and prioritization

• 28:51Speaker 03

  that's sort of backed by this cohesive plan around how we're going to ultimately win within the target market that we're going after.

• 28:59Harry Stebbings?

  Can you expect a candidate to know that? And what I mean by that is that I may be a brilliant product leader. I just don't know Calendly as a business anywhere near as well as you do. And so it might be quite a base strategy to you, but I might still be a brilliant product leader. Is it wrong to expect them to come up with this strategic wisdom on a business that they don't know?

• 29:18Speaker 03

  Most of the competency questions typically will you'll see them happen either through the lens of use something from your experience. So tell me about a time when, you know, you created a product strategy or a winning product strategy that ultimately, you know, ended in some sort of positive impact to the business. And so you let them use their experience to, to help describe to you how they would approach a problem, or use a hypothetical, which sort of puts you on the same footing as the candidate of, you know, neither one of us necessarily know, know much or are experts in this space, but you sort of use a hypothetical. This set of the interview process should all about be drawing on your past experience and sort of using hypotheticals. When you move into the last phase, which is, we call it kind of a collaborative working session. You see companies call it sort of the presentation. That's when you're really trying to get down to the brass tacks of how would you approach this job?

• 30:03Speaker 03

  Then you give them the opportunity of time and space and the ability to really think deeply about your product. And the prompt there could be much more around what you might expect, the types of problems they need to solve in this role. So if they're a growth product manager, it might be, you know, look through and play around with our signup and setup and onboarding flow and identify where the biggest opportunity is to improve activation, right? You're trying to understand how would they approach the actual job that they'd be hired to do. But I think in that panel interview, you can be much more explicit around drawing on their past experience as well as creating hypotheticals.

• 30:35Harry Stebbings?

  I'm so glad you brought up the presentations. For the presentations, we give them kind of the problem use case, say. How long do we give them? What materials do we give them? Who comes to the actual presentation? How's it structured? Never done it before, so I'm learning from you.

• 30:49Speaker 03

  I think it's really important to be clear with candidates how much time you want them to spend on these presentations. So you want to time box it, and that also will allow for consistency in terms of being able to evaluate across candidates. If everyone sort of said, you know, don't spend more than five hours on this presentation, then you sort of can see the work output from a similar amount of time being spent. So I think that's the first. The second is, you know, the prompt typically is something around your business and how they would actually tackle a real problem within your business. At least that's how we do it here at Calendly. And it really allows you to hear more around how they would approach a problem they might see in the wild. And then the third piece, I think this may be the most important part, which is, to me, the presentation is actually less about me as a hiring manager or a product leader sitting on a panel.

• 31:31Speaker 03

  Yes, it's very important as part of the overall valuation, but I think it's more important for the candidate to actually dig into the details of what is the types of problems I'd be working on day to day? And is this actually the work I want to be doing? And I find more often than not, the presentation is a wonderful way to weed out candidates who, you know, thought they were maybe going to be doing one job, and then they got the sort of presentation and learned, you know, I'm not exactly sure those are the problems I want to be tackling in my next role. And it's actually a really great opportunity to have alignment long before there's a hire made around what are the types of problems you'd be facing in the role.

• 32:03Harry Stebbings?

  What are the single biggest mistakes you think founders make in hiring this senior product PM slash product leader? What do I need to be wary of?

• 32:11Speaker 03

  Yeah, I think on the leader's side, some of the things we've already touched on around just sort of misalignment around what the org needs. And so again, they hire an executor when they need a visionary, or they hire a visionary when they need an executor. So I think on the leader's side, it's much more around the missteps happen when you're not either honest with yourself or explicit around what you're actually trying to optimize for. On the PM's side, I think it's actually more when there's misalignment on where the company is in their growth curve and therefore what the actual role of a product manager is. So some PMs who are really great at early stage, you know, they feel stifled at late-stage companies. They don't like process. They don't want to have to do a bunch of updates and provide statuses. And then you've got folks who are great at late-stage, but they really can't handle the ambiguity of early-stage.

• 32:55Speaker 03

  And so I think you kind of call this the like product manager and growth. Fit, that's usually when I see the biggest challenges with hires is they aren't able to actually adapt to the needs of what the role is based on where the company is in their growth curve.

• 33:08Harry Stebbings?

  So if we say we hire this very new candidate and they're actually a junior, they're a junior in the product team, and we think back to their early career, what are the most important skills to build early on in your career in product, do you think?

• 33:21Speaker 03

  I think at the very beginning, it's all about those core PM fundamentals. It's all about honing everything from problem prioritization, being able to use that product sense to be able to figure out how you build a winning product solution, mastering communication and storytelling and getting people on board with what you need to get built. And then, you know, building that analytical thinking muscle to be able to make sure you're setting the right KPIs and success metrics so that after you release something, you have a way to understand whether whether it's working or not. And if it's not, you know, you test and learn until you get it right. So I think that that is the most important thing is nailing those fundamentals. I think as you start to move up in your career, a couple of things happen. I think the first is you have to do those same things, but with a larger scope and with more complexity and do it with more autonomy. And so the same fundamentals are going to be there.

• 34:06Speaker 03

  It's just that they're going to become more high stakes and the scope will be will be bigger and the problems will be more complex. And then I think also, as you start to move up, you do go from sort of that execution to strategy ownership. And so early stage PM, then it's really all about execution and showing and demonstrating that you can deliver value and impact to the business. And then as you sort of start to get promoted and you move higher up in in sort of the the organization, you you start to own more of that strategy and you're really responsible for building that strategy and then working with the teams on execution.

• 34:37Harry Stebbings?

  And speaking of complexity and and big bets as you scale into even more of a heroic sales leader, resource allocation is tough. Do you favor concentrated bets, heavy concentrated resource allocation? Or do you prefer gatted bets and seeing which flowers bloom? It's almost like venture in some ways. How do you approach resource allocation?

• 34:57Speaker 03

  I think this really depends on where you are in your company's growth. If you are pre-product market fit, your only job is to get to product market fit. If you sort of see early signs of product market fit, your job is to get that thing coming and scaling and repeatable. And you know, you want to make this thing that's it's starting to blossom, you know, blossom even more. And then as you get into, okay, this thing is blossoming, now I gotta go find the next growth level, then that changes as well. So I think the kind of most important element of this is actually making sure there's really strong alignment at the company level around, again, kind of where you are in your growth curve, but then therefore how you have to think about investing in the core product that exists today or placing bets for the future. And I think ways to sort of mitigate this risk really start with having a really clear product strategy. If you know where you're trying to go over the next couple of years

• 35:42Speaker 03

  and how the bets that you want to place a year or two years from now, then you work backwards from that to say, we actually have to start working on at least the discovery and the research and design for the thing we want to launch, you know, six, nine, 12 months from now. And so the resource allocation, I think, can really be driven by a clear and articulate product strategy. And I think the second thing is, you know, as companies go into scale and and get larger and larger, sort of that culture of innovation, you have to really foster that. And you have to find ways to ensure that individuals in the organization continue to feel really empowered, whether it's through innovation sprints every quarter or continuing hackathons, whatever it is, making sure that there's a real culture of of innovation so that that doesn't sort of, you know, slowly fade away as the business grows and scales.

• 36:26Harry Stebbings?

  How often do you revisit product strategy and when is the time to change it? If something's not looking good, how do you give enough data, but also not too much that it's out there for too long?

• 36:37Speaker 03

  I think a good time horizon for the combination of the product vision and strategy is, call it two to three years. You then take that strategy, and again, I mentioned a little bit of around of a horizon framework, which is what we use at least at Callonley. You know, we are in this horizon today. We will exit this horizon when we have met X, Y, and Z criteria and move to the next horizon. And then with it, while we're in this horizon, here are the things we need to do over the next six months to get us closer to essentially feeling like we've gotten to the place that we can exit this horizon. So two to three Years is reasonable length of time that it would take to actually execute on your current product strategy. I think you reevaluate it quarterly and it doesn't mean you're going to change it quarterly. You know, on a quarterly basis, you should be looking at the data, you should be looking at the market, you should be looking at the competition.

• 37:21Speaker 03

  You should be looking at the users and the the sort of mix of your users and saying, do we still have it right? Is this still the right strategy? So I think it's check it often, hopefully you're not changing it every quarter and hopefully it's something that can endure, call it two to three years.

• 37:33Harry Stebbings?

  Penultimate one, how impacted do you think you are by your competitors' product strategy? It's hard not to be. Everyone's like, no, row your own race, but it's hard. You look to the side and ooh, they did that. Ooh, that looks good. How impacted are you?

• 37:46Speaker 03

  Pay attention and understand and learn. I try very hard to focus on our customers and our users. If we're really clear and articulate around our strategy, unless there's something our competition is doing that should make us materially doubt our strategy. I think, you know, we will gain far more by maniacally focusing on what we believe we need to do to win versus chasing what another product's doing. I think the other thing around competitors, you often see, oh, competitor just launched X feature. In reality, sure, you may like live in the same space, but you're not actually really competitor products, right? We might be solving, for example, the external scheduling use case for small teams or large teams. And that might be all about calendar productivity. And so from the outside, you see, oh, these two companies are competitive and look, they've launched this feature.

• 38:29Speaker 03

  In reality, if we have a really clear product strategy, we shouldn't build that feature because it's not in service of what we believe we need to do in order to be able to go and win.

• 38:37Harry Stebbings?

  Speaking of product strategy and decisions, can you tell me a story of a product decision that you made that was a mistake? And what did you learn from it?

• 38:45Speaker 03

  Yeah, so I went to Box after my startup and back in two thousand twelve. And had the opportunity to actually build our first transition from single product to multi-product portfolio. We did a ton of customer diligence, we did a bunch of market analysis, we had a very clear prototype, we validated with customers. We felt pretty confident that there was going to be sort of quote unquote product market fit with this new product. And so we made very aggressive revenue projections around what we believe we could deliver out of this new product in year one, in year two and year three. And so year one, we went to market, lots of excitement from our sales team, lots of excitement from our customers. But we missed those internal projections around what we believed we could deliver to the business pretty substantially. And there were really a couple of learnings from that experience. By year two and by year three, we had caught up to our projections.

• 39:30Speaker 03

  So it wasn't a matter of missing the mark. In terms of the product decision, a lesson for me was really more around bringing new products to market within an organization where you already have a very successful core product. Two things about it. One, it always takes much longer for the sort of payoff of that investment to really start to materially lift and impact the business. And the second is if you have a sales organization who knows how to sell an existing product and they know how to meet their quota with that product, unless you create incentives and you find a way to sort of force them to start to sell this new product, they're always going to go to the path of least resistance of essentially, how do I meet my quota? And so it was a real lesson to me, if you can't just build a product and launch it

• 40:12Speaker 03

  and expect that the business is going to be there, there's a lot of go-to-market implications on these new products that you have to be ahead of if you're going to expect to see a real material lift in sort of year one.

• 40:21Harry Stebbings?

  So what would you do differently as a result?

• 40:23Speaker 03

  Two things. One, I would be more realistic with my expectations and the modeling that we did around when we could expect the actual revenue. But I think more importantly, I would partner more closely with and integrate more closely into the sort of selling motion and get the upfront commitment and buy-in from the sales leader or CRO, whoever that might be, that when we bring this new product to market, we're also going to do X, Y, and Z to ensure that the sales reps are incentivized to actually sell the product and actually allow us to potentially hit our target for year one.

• 40:54Harry Stebbings?

  Annie, I'm going to move into a quick fire round. So tell me, when do you listen to users versus when do you ignore them?

• 41:00Speaker 03

  You always listen, but make sure you have a sort of framework to judge whether the users you're listening to are sort of mass market or more of an edge case.

• 41:09Harry Stebbings?

  Which product leaders outside of Callan need you most admire?

• 41:12Speaker 03

  I'm a big fan of a few kind of former product leaders who are now sort of helping to educate the market on best-in-class product management and kind of how to build high-functioning product teams. So Gibb Biddle, who is the former VP of Product at Netflix, he writes and teaches a lot about product strategy. I've been able to learn a lot from him. Teresa Torres, she runs Product Talk and teaches a lot about continuous discovery. And then, of course, Marty Kagan. Of the Silicon Valley Product Group, really helping product leaders create empowered product teams and helping to really focus on how you deliver better results to the organization. So I really like to draw from several leaders who have now kind of moved more into the teaching and take those lessons to my team.

• 41:49Harry Stebbings?

  What one piece of advice would you give to a product leader starting a new role today?

• 41:53Speaker 03

  I would approach it like you would managing any product. I would say, what is the impact you ultimately want to deliver after your first year and kind of work backwards from there to create a roadmap of, you know, what do you need to do in the first 90 days? What do you need to do in the first half? What do you do in the second half of how you're going to actually ultimately deliver that impact by the end of the year?

• 42:12Harry Stebbings?

  What would you most like to change about the world of product?

• 42:14Speaker 03

  I would love to see more folks transition into product management from other disciplines like customer success and support, product marketing. I think this sort of diversity of thought and experience and background that a team can really learn from, from folks who come from all different parts of organizations. This can really drive kind of an outsized impact on the solutions ultimately you're delivering to customers. So I just love to see more sort of internal mobility across organizations from folks moving into product management from other disciplines.

• 42:41Harry Stebbings?

  Other than Calendly, which other company product strategy have you been most impressed by recently?

• 42:47Speaker 03

  I think the way that Slack has actually been able to successfully replace the majority of my email communication, which I was very leery of when they first sort of came out with the product and sort of stated that, or maybe didn't fully state it, but that was the goal. So I've been pretty impressed by how well Slack has been able to execute on sort of their strategy to ultimately sort of remove a lot of communication that maybe traditionally would have happened through email. Doesn't happen, you know, either asynchronously or synchronously through Slack.

• 43:14Harry Stebbings?

  Annie, listen, thank you so much for this. I'm sorry for the wayward questions, but I absolutely loved having you on and I can't thank you enough for sharing the wisdom with me.

• 43:22Speaker 03

  Thanks, Harry. I really enjoyed it.

• 43:24Harry Stebbings?

  I mean, I so loved that discussion. Such natural, free and open conversation. Annie, I so appreciate you putting up with my very wayward questions, completely off schedule. Huge thank you again to Annie for giving up the time. And if you'd like to see more from us behind the scenes, of course you can, on 20vc.com. We always love to see you there. But before we leave you today, you have to check out builder. AI. They make building software so easy that anyone can do it. If you have a vision, you can build it with builder.ai. And one of my favourite products of theirs is Studio Rapid. I always think the number one reason people fail is they don't start. And Studio Rapid is the perfect tool for when you need an MVP fast. And when I say fast, you can build simple, beautiful native apps in less than one day. But don't just take my word for it.

• 44:08Harry Stebbings?

  Take the words of BBC, Pepsi, Fujitsu, some of the world's leading brands, all loving and using the builder.ai product suite. Head over to builder.ai to find out more. And speaking of creating beautiful customer experiences and products, if your business runs on a mobile app, you have to check out UX Cam, designed specifically for mobile product teams. UX Cam helps build better apps by making user motivations and frustrations loud and clear. Product teams love this app experience analytics platform that empowers them with clarity and speed. UX Cam also captures billions of micro-interaction level data like screen swipes and taps. With tools like session replay, heap maps, funnels, crash analytics and auto-capture of user frustrations and bugs,

• 44:52Harry Stebbings?

  it has never been easier to uncover real user behaviour. Join over 30,000 apps, such as Costa Coffee, Nando's, Delivery Hero and Rappi, who optimise their product with UX Cam. If you're not using UX Cam, what are you waiting for? Go to uxcam.com/20vc to claim your free two-month extended free trial. As always, I so appreciate all your support and I can't wait to bring you an incredible episode this coming Friday with Rene Haas, CEO at ARM.