The Exchanges

Q I'm so glad you brought up the presentations. For the presentations, we give them kind of the problem use case, say, um, 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.

A Yeah, varies. Absolutely. Uh, company to company. I think it's really important to be Clear with candidates how much time you want them to spend on these presentations. Um, I think it's really important to acknowledge the time that's being spent on the presentation. So you want to time boxes 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 out, the work output from, from a similar amount of, of time being spent. So I think that's the first. Uh, the second is, you know, the prompt typically is something, uh, around your business and, and how they would actually tackle a real problem within your business. At least that's how we do it here at Calendly. Um, and 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. Um, yes, it's very important as, as, as, as part of the overall evaluation, 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 this is actually the work I want to be doing. And I …

AI assessment note: “don't spend more than five hours on this presentation... prompt typically is something around your business”

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

A Yeah, I think on the leader side, you know, some of the things we've already touched on around just sort of misalignment, uh, around what the org needs. And so again, you know, 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 side, it's much more around, um, the, the, the missteps happen when you're, you know, sort of not either honest with yourself or, uh, or explicit around what you're actually trying to optimize for. On the PM 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. Uh, so some PMs who are really great at early stage, um, you know, they feel stifled at late stage companies. They don't like process. They don't want to have to, you know, do, uh, you know, um, a bunch of updates and, and, and, uh, provide statuses. Uh, and then you've got folks who are great at late stage, um, but they really can't handle the ambiguity of early stage. And so I think. You kind of call this the like, uh, you know, product manager and sort of, um, growth fit. Uh, and I think that's usually when I see the, the, 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.

AI assessment note: “they hire an executor when they need a visionary or they hire a visionary”

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

A Yep. So again, I think this really depends on where you are in your company's growth. And so if you are, you know, pre-product market fit, your only job is to get the product market fit. Uh, if you sort of see early signs of product market fit, your job is to get that thing humming 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. Uh, and then as you get into, okay, this thing is blossoming. Now I got to go find the next, the next growth level, then, 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 and how, um, you know, the, the bets that you want to place, you know, 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. Um, and so the resource allocation I th…

AI assessment note: “I think this really depends on where you are in your company's growth.”

Q 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?

A I personally try to, um, pay attention and, and understand and learn, but I try very hard to focus on our customers and our users. Um, and, and again, 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. Um, I think, you know, we will gain far more by maniacally focusing on what we believe we need to do to win versus chasing, uh, you know, what another product's doing. I think the other thing around competitors, Is you often see, oh, they're, you know, competitor just, just launched X feature in reality. Sure. You may like live in the same space, but you're not actually really competitor products, right? Uh, you know, you, 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'd launched this feature. In reality, 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, uh, in order to be able to go and win.

AI assessment note: “I personally try to, um, pay attention and, and understand and learn, but”

Q 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?

A Yeah, I think at the beginning you really want to focus on finding where's the sort of most acute, uh, sort of visceral pain points that someone might have within some sort of problem space or some sort of market. Uh, and it may feel really narrow, uh, may feel really narrow at the beginning, but I think the mistake that early stage founders take, make, and we certainly, we certainly struggled with this, uh, at our startup as well is sort of, um, the shiny objects, right? We came in saying we have this really acute pain point around, uh, private market liquidity. And being able to, to, to sort of provide private market liquidity to employees and shareholders, given how long it takes to have, you know, some sort of exit. But then we, you know, said, well, let's also do a capital raising platform. Oh, and let's also build a data, 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 sort of decided to build new products far too soon. And I think that's, that's probably my biggest lesson from that experience.

AI assessment note: “focus on finding where's the sort of most acute, sort of visceral pain points”

Q 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?

A I personally try to, um, pay attention and, and understand and learn, but I try very hard to focus on our customers and our users. Um, and, and again, 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. Um, I think, you know, we will gain far more by maniacally focusing on what we believe we need to do to win versus chasing, uh, you know, what another product's doing. I think the other thing around competitors, Is you often see, oh, they're, you know, competitor just, just launched X feature in reality. Sure. You may like live in the same space, but you're not actually really competitor products, right? Uh, you know, you, 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'd launched this feature. In reality, 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, uh, in order to be able to go and win.

AI assessment note: “I try very hard to focus on our customers and our users”

Q of PLG, product marketing matters more than ever because you don't have the stabilizer of the sales rep. Um, I think product marketing today is really, really shit. Um, it's bland. It doesn't make you feel anything. Um, 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?

A It's a great question. You know, I, I actually would start with I think that great marketing of PLG products, uh, is not actually about product marketing. It's about the actual product itself. Um, and so the product quote unquote marketing is I use the product. I introduced 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 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. Uh, I think then as you start scaling and actually start moving on market, that's where the product marketing team really becomes much more in embedded into the product org, 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, um, you know, introducing the product to different buyer segments and product marketing. 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 jus…

AI assessment note: “great marketing of PLG products, uh, is not actually about product marketing. It's about the actual product itself.”

Q at the different, um, 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-like growth organization into a verticalized sales approach dependent on the function that you're selling into? And how does the org change with product-like growth chapter one to verticalize use cases number two?

A Great question. Uh, 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, 80% of the functionality we have today will solve the use cases of those departmental users. Um, and then there's some functionality that very specifically is for the departmental users, but actually crosses across departments. Right? 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. Uh, you've got multiple individuals in an organization who need to schedule time with someone externally. Um, we could use that same functionality to support multiple verticals, which is what we call collective event type, a certain type of meeting to support that kind of collaborative use case within the organization. So you get a lot of benefit from starting horizontal, call it And then when you go vertical, you try really hard to say, what are the things we can go build that are actually going to solve for problems across multiple of these, uh, departments? And we, 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 focus…

AI assessment note: “we're not looking to be a point solution just for sales reps”

Q I'm so glad you brought up the presentations. For the presentations, we give them kind of the problem use case, say, um, 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.

A Yeah, varies. Absolutely. Uh, company to company. I think it's really important to be Clear with candidates how much time you want them to spend on these presentations. Um, I think it's really important to acknowledge the time that's being spent on the presentation. So you want to time boxes 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 out, the work output from, from a similar amount of, of time being spent. So I think that's the first. Uh, the second is, you know, the prompt typically is something, uh, around your business and, and how they would actually tackle a real problem within your business. At least that's how we do it here at Calendly. Um, and 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. Um, yes, it's very important as, as, as, as part of the overall evaluation, 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 this is actually the work I want to be doing. And I …

AI assessment note: “the prompt typically is something, uh, around your business”

Q at the different, um, 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-like growth organization into a verticalized sales approach dependent on the function that you're selling into? And how does the org change with product-like growth chapter one to verticalize use cases number two?

A Great question. Uh, 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, 80% of the functionality we have today will solve the use cases of those departmental users. Um, and then there's some functionality that very specifically is for the departmental users, but actually crosses across departments. Right? 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. Uh, you've got multiple individuals in an organization who need to schedule time with someone externally. Um, we could use that same functionality to support multiple verticals, which is what we call collective event type, a certain type of meeting to support that kind of collaborative use case within the organization. So you get a lot of benefit from starting horizontal, call it And then when you go vertical, you try really hard to say, what are the things we can go build that are actually going to solve for problems across multiple of these, uh, departments? And we, 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 focus…

AI assessment note: “this is the beauty of starting off horizontally and then going vertically”

Q 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 it enough data, but also not too much that it's out there for too long?

A Yeah. I think a good time horizon, a realistic time horizon for kind of the combination of, of the product vision and strategy is call it two to three years. Um, and I think that you then take that strategy. And again, I mentioned a little bit of a round of sort of, of a horizon framework, which is Uh, what we use at least at Calendly. Um, you know, we are in this horizon today. We will exit this horizon when we, you know, have met X, Y, and Z criteria and move to the next horizon. Uh, and then with it, while we're in this horizon, here are the things we need to do over the next six months to make us, you know, get us closer to essentially feeling like we've gotten to the place that we can exit this horizon. Um, so, you know, I think two to three years is, is reasonable in the sense of, uh, a timeline that you would have, you know, a length of time that it would take to actually execute on your current product strategy. I think you reevaluate it, uh, quarterly. I mean, it doesn't mean you're going to change it quarterly, but, 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. You should be looking at the users and the sort of mix of your users and saying, do we still have it right? Is this still the right strategy? Um, so I think it's, Check it often, but, you know, hopefully you're n…

AI assessment note: “I think you reevaluate it, uh, quarterly. I mean, it doesn't mean you're going to change it”

Q I'm excited for this one. I have to say, so let's start with a little bit on you. So you've led some of the most fantastic product orgs and most 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?

A Yeah, absolutely. So, uh, started my career off actually intending to be a lawyer. Uh, 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, um, and 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, uh, 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, uh, called Expert Financial. And we were trying to create a stock market, but for private companies. Um, and so, yeah, 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. Um, and my time, you know, at expert was 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. Uh, I think that experience really taught me about sort of the power of focus. Uh, especially in the early days of finding product market fit, just how important it is to kind of maniacally focus on solving one problem, uh, and solving it better than any alternative, um, on the market. Um, so yeah, from there I went through, yeah.

AI assessment note: “So that's really how I got into product management.”

Q Can you do PLG and enterprise from day one?

A It's a very good question. Uh, I don't know that you need to. Um, I think that the beauty of the PLG business is that it enables you to build a highly profitable Uh, uh, 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 sort of get the opportunity to then go invest in sales and marketing dollars to unlock the larger deals. So it's a, the beauty of the business model is it's much cheaper. Uh, 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 you're able to unlock a much more efficient business, which allows you to then sort of, you know, 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, and move on market. Uh, I think it's also the other thing I'll say on that is I think it's also really, it's much harder to scale down than it is to scale up. Um, and then when I was at Glassdoor, I had the opportunity to, um, build our self-service business from the ground up. Uh, when I joined, we were very much a enterprise focused business. We had a huge d…

AI assessment note: “I don't know that you need to. Um, I think that the beauty”

Q Is there a second product? And, If so, is, isn't, isn't like, it's not so well known obviously cause it's so dominant within and if not, have you not waited too long?

A Yeah, 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 or you're, you know, a lawyer or a real estate agent, or you own a nail salon all the way to a sales rep in an organization or a customer success rep in an organization. Um, you know, 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, uh, you know, sort of first act of Calendly. And that's really, we grabbed a lot of market share, uh, and became kind of ubiquitous. Where 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 sales, that's, um, recruiting, that's customer success. Anyone who's in an externally facing role, Calendly can play a really great role in helping you schedule your meetings more efficiently. So that's the phase we're in today, going deeper there. The third phase where I think we'll go eventually is beyond that and to really try to own and, and, um, and, uh, help support and deliver on the entire meeting life cycle. So scheduling is really just a wedge…

AI assessment note: “So I think about Calendly as our history and where we've come to date”

Q Is there a second product? And, If so, is, isn't, isn't like, it's not so well known obviously cause it's so dominant within and if not, have you not waited too long?

A Yeah, 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 or you're, you know, a lawyer or a real estate agent, or you own a nail salon all the way to a sales rep in an organization or a customer success rep in an organization. Um, you know, 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, uh, you know, sort of first act of Calendly. And that's really, we grabbed a lot of market share, uh, and became kind of ubiquitous. Where 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 sales, that's, um, recruiting, that's customer success. Anyone who's in an externally facing role, Calendly can play a really great role in helping you schedule your meetings more efficiently. So that's the phase we're in today, going deeper there. The third phase where I think we'll go eventually is beyond that and to really try to own and, and, um, and, uh, help support and deliver on the entire meeting life cycle. So scheduling is really just a wedge…

AI assessment note: “scheduling is really just a wedge into a much broader meeting lifecycle.”

Q Can you do PLG and enterprise from day one?

A It's a very good question. Uh, I don't know that you need to. Um, I think that the beauty of the PLG business is that it enables you to build a highly profitable Uh, uh, 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 sort of get the opportunity to then go invest in sales and marketing dollars to unlock the larger deals. So it's a, the beauty of the business model is it's much cheaper. Uh, 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 you're able to unlock a much more efficient business, which allows you to then sort of, you know, 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, and move on market. Uh, I think it's also the other thing I'll say on that is I think it's also really, it's much harder to scale down than it is to scale up. Um, and then when I was at Glassdoor, I had the opportunity to, um, build our self-service business from the ground up. Uh, when I joined, we were very much a enterprise focused business. We had a huge d…

AI assessment note: “I don't know that you need to.”

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

A Yep. So again, I think this really depends on where you are in your company's growth. And so if you are, you know, pre-product market fit, your only job is to get the product market fit. Uh, if you sort of see early signs of product market fit, your job is to get that thing humming 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. Uh, and then as you get into, okay, this thing is blossoming. Now I got to go find the next, the next growth level, then, 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 and how, um, you know, the, the bets that you want to place, you know, 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. Um, and so the resource allocation I th…

AI assessment note: “I think this really depends on where you are in your company's growth.”