The Exchanges

Q Are there commonalities in the competencies that we look for? What, what are those if there are some commonalities?

A For me, I'd look at really kind of four main components of what I would expect out of a product manager. So 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 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 sort of the bucket there and leadership and communication and execution. And then lastly, can you sort of set up the right success metrics 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, leadership, communication, execution, and analytical thinking tend to be sort of the different buckets that most product organizations are looking for in product managers.

AI assessment note: “I'd look at really kind of four main components of what I would expect”

Q Are there commonalities in the competencies that we look for? What, what are those if there are some commonalities?

A For me, I'd look at really kind of four main components of what I would expect out of a product manager. So 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 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 sort of the bucket there and leadership and communication and execution. And then lastly, can you sort of set up the right success metrics 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, leadership, communication, execution, and analytical thinking tend to be sort of the different buckets that most product organizations are looking for in product managers.

AI assessment note: “I'd look at really kind of four main components of what I would expect”

Q Which product leaders outside of Calendly do you most admire?

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

AI assessment note: “So Gibb Biddle, who is the former VP of product at Netflix”

Q Can I ask the other one is like, it's probably again, I'm peppering you for questions here. Is product art or science? I'm always like edging between the two and I'm never really sure where I land because it's so back and forth. How would you think about that?

A Yeah. 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 you people using the product today? Where do they have challenges when they're using it? Uh, who are 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. I think when it comes to, and so 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. Uh, and there's this definition of sort of quote unquote product sense that, that we talk about a lot, which is just sort of this combination of, you know, curiosity and creativity and intuition around how to solve a problem. Uh, and that to me is something that's, that of course you can still use some science. You'll do discovery. You'll talk to customers. They'll get input, but at the end of the day, there's a l…

AI assessment note: “science can be very well applied to that first part... much more art”

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

A Yeah, I, for me, I look at really kind of four Main components of, of, uh, what I would expect out of product managers. The first is really all about sort of synthesizing large amounts of information, um, and data points and being able to use that to prioritize the right problems to solve. You might call that sort of strategy. Um, the second bucket is, can you then use your curiosity, your creativity, you know, your intuition to sort of 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. Uh, 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 sort of the bucket there is leadership and communication and execution. And then lastly, can you sort of set up the right Success metrics 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, um, you know, most product organizations are looking for in product managers.

AI assessment note: “I look at really kind of four Main components of, of, uh, what I would expect”

Q There are like two million in ARR, and they're going, we're going to layer on enterprise, and I just get very worried. 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?

A Yeah, I think any of you, um, to start, 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, um, you know, definitely want to, want to be very careful around making sure you're timing it right. Um, I think, you know, one of the, the pulling mechanisms you see really is in usage data. And so Calendly, what we started to see was these core ICPs, sales, recruiting, you know, um, our, our customer experiences teams within organizations starting to become, um, you know, some level of, of mass, right? 50 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 sort of hit a threshold where, um, if we were to go have a conversation with someone internally, there's enough mass here, uh, that that conversation would be productive. And there's a likelihood that they would actually want to standardize Calendly on Calendly, uh, you know, beyond just the department or the subset of users that are using it today. So I think you have to use the data, uh, to, to really help inform, are you ready? Um, and then I think maybe even a more important question is, are you ready organiz…

AI assessment note: “one of the, the pulling mechanisms you see really is in usage data.”

Q 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?

A Yeah. So I think, uh, really the high, at the highest level, there's just an increased complexity that sort of happens across the whole organization, right? For, for the product or, 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, uh, you know, on the, um, sales team 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, that's working with our large customers. So everywhere across the organization, you're sort of getting complexity within those departments. I think the second thing that happens, not just within each department, but as in across departments. And so all of a sudden, now you have these dependencies popping up everywhere, right? Product can no longer just go build an AB 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 teams. So all of a sudden you've got like…

AI assessment note: “there's just an increased complexity that sort of happens across the whole organization”

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

A Yeah, I, for me, I look at really kind of four Main components of, of, uh, what I would expect out of product managers. The first is really all about sort of synthesizing large amounts of information, um, and data points and being able to use that to prioritize the right problems to solve. You might call that sort of strategy. Um, the second bucket is, can you then use your curiosity, your creativity, you know, your intuition to sort of 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. Uh, 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 sort of the bucket there is leadership and communication and execution. And then lastly, can you sort of set up the right Success metrics 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, um, you know, most product organizations are looking for in product managers.

AI assessment note: “I look at really kind of four Main components of, of, uh, what I would expect”

Q and I think Shrey Asdoshi says this girl, visionaries early, 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 in artistry and the Art with scale of product management of teams. Do you know what I mean?

A 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. The mistakes that I see happen is that the CEO founder goes to hire for a skill set 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 that vision. Well, then you're just going to clash or opposite, right? You really need someone who's going to bring that vision. The founder or CEO has moved into a much different role, but you go hire 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.

AI assessment note: “Absolutely not. And the best product companies out there find a way not to.”

Q Shreyas is just incredible, but now I want to move to Annie Pearl. Now, Annie is the CPO at Calendly, the company that makes Scheduling meetings simple and painless, and before Calendly, Annie lagged Glassdoor's product vision and user experience, managing a seventy-person product and design org. When do I hire a CPO or a head of product? What are the signals that now is the right time?

A The journey around when to bring in a product leader really, really corresponds to where a company is in their growth trajectory. Pre-product markets sit, founders usually doing most of the product management, working directly with the engineers, getting things built. So then usually, you know, you find product market fit 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. 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 becomes not just executing the founder's vision, but how do I keep predictability? How do I create repeatability? 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 hyper growth 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 seen the movie play …

AI assessment note: “that's where you typically see someone bringing in a CPO”

Q Shreyas is just incredible, but now I want to move to Annie Pearl. Now, Annie is the CPO at Calendly, the company that makes Scheduling meetings simple and painless, and before Calendly, Annie lagged Glassdoor's product vision and user experience, managing a seventy-person product and design org. When do I hire a CPO or a head of product? What are the signals that now is the right time?

A The journey around when to bring in a product leader really, really corresponds to where a company is in their growth trajectory. Pre-product markets sit, founders usually doing most of the product management, working directly with the engineers, getting things built. So then usually, you know, you find product market fit 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. 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 becomes not just executing the founder's vision, but how do I keep predictability? How do I create repeatability? 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 hyper growth 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 seen the movie play …

AI assessment note: “hyper growth or late stage... that's where you typically see someone bringing in a CPO”

Q and I think Shrey Asdoshi says this girl, visionaries early, 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 in artistry and the Art with scale of product management of teams. Do you know what I mean?

A 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. The mistakes that I see happen is that the CEO founder goes to hire for a skill set 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 that vision. Well, then you're just going to clash or opposite, right? You really need someone who's going to bring that vision. The founder or CEO has moved into a much different role, but you go hire 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.

AI assessment note: “Absolutely not. And the best product companies out there find a way not to.”

Q I think. And so when we think about this discussion, uh, so many founders listen to the show and, uh, you're going to be a hypothetical angel in my company. Thrilled to have you. Thank you. Uh, wonderful. Um, uh, 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?

A Yep. 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. So pre-product market fit, you know, uh, founders usually doing most of the product management, working with directly with the engineers, getting things built. Um, then usually, you know, you sort of find product market fit 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. Um, 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, you know, things are working well, we're humming, uh, then your job as the product leader becomes not just executing the founder's vision, but how do I keep predictability? How do I create repeatability? How do I start to hire, um, you know, a team and start to make this machine move faster, uh, to continue to essentially execute. And then I think you hit another phase, which I'll just call kind of hyper growth or late stage where A little bit of what we've already talked about. You have a product and it's humming, and now it's time to, to open up new growth levers. So you're talking about new produ…

AI assessment note: “when to bring in a product leader really, really corresponds to where a company is”

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

A Yeah, I think you sort of get to a place with your first product where, um, you know, it's very clear that you found product market fit, right? Your target customers are actually using and buying and talking about your product. Um, there's a lot of definitions out there of what product market fit is. I think that, you know, sort of when you see it, you feel it, uh, and you know, it's there. Um, and I think you have to be really diligent of, of even once you've found product market fit, really doubling down and scaling the existing product for quite some time period. Um, and then you sort of get to a place where, okay, things are pretty repeatable. Things are pretty predictable. Growth is, you know, uh, something that we can really model out. Now let's actually start to think about what the next product is to build. Um, and, and I think actually maybe one of the bigger mistakes that companies make is doing that too late. Um, 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 as they find themselves behind the eight ball, uh, having not actually invested early enough, or at least laid the foundation for what they might want to do, um, as their second product.

AI assessment note: “things are pretty repeatable. Things are pretty predictable.”

Q 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?

A Yeah. So I think, uh, really the high, at the highest level, there's just an increased complexity that sort of happens across the whole organization, right? For, for the product or, 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, uh, you know, on the, um, sales team 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, that's working with our large customers. So everywhere across the organization, you're sort of getting complexity within those departments. I think the second thing that happens, not just within each department, but as in across departments. And so all of a sudden, now you have these dependencies popping up everywhere, right? Product can no longer just go build an AB 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 teams. So all of a sudden you've got like…

AI assessment note: “there's just an increased complexity that sort of happens across the whole organization”

Q There are like two million in ARR, and they're going, we're going to layer on enterprise, and I just get very worried. 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?

A Yeah, I think any of you, um, to start, 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, um, you know, definitely want to, want to be very careful around making sure you're timing it right. Um, I think, you know, one of the, the pulling mechanisms you see really is in usage data. And so Calendly, what we started to see was these core ICPs, sales, recruiting, you know, um, our, our customer experiences teams within organizations starting to become, um, you know, some level of, of mass, right? 50 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 sort of hit a threshold where, um, if we were to go have a conversation with someone internally, there's enough mass here, uh, that that conversation would be productive. And there's a likelihood that they would actually want to standardize Calendly on Calendly, uh, you know, beyond just the department or the subset of users that are using it today. So I think you have to use the data, uh, to, to really help inform, are you ready? Um, and then I think maybe even a more important question is, are you ready organiz…

AI assessment note: “one of the, the pulling mechanisms you see really is in usage data.”

Q 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?

A I think for me and, and what you typically see is the prioritization. Um, 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? Um, are we okay, for example, with Slower growth in sort of the PLG business for some time period while we're investing in, in, 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, to, to grow at really high rates of PLG. So I think the, the most important and the biggest challenge the organization stays 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, uh, you know, the self-service buyer? Am I supposed to be thinking about a departmental use case? 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.

AI assessment note: “the biggest challenge the organization stays is not having that alignment at the executive level”

Q So when we think about the hiring process, again, I'm a young first time founder, but my company is fantastic. Um, and you're an angel, so lucky. Um, 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?

A Yep. 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 or your company? This can vary company to company. Um, and as we've already talked about the definition of what product management is, uh, even something that is Uh, 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? Um, and so once you sort of have at least a general framework for what you're looking for for candidates, then it typically goes through sort of a three part process. The first is usually the hiring manager phone screen. Uh, or the first sort of meeting with the hiring manager. This is typically where you want to really understand more deeply their background and their experience and their skillset. Uh, and maybe even most importantly, their interest in the role. Uh, and if you can get ahead of, you know, sort of wasting time across the whole interview process, just to find out that, you know, really this person's interests don't really align with, with the role. You'll…

AI assessment note: “once you sort of have at least a general framework... then it typically goes through sort of a three part process.”

Q So if we say we hire this very new candidate, and they're actually a junior, uh, let's take this as an example. They're a junior in the product team, and we think back to their early career. Um, what are the most important skills to build early on in your career and product, do you think?

A I think at the very beginning, it's all about those core PM fundamentals, right? It's all about honing everything from Uh, you know, problem prioritization, being able to use that product sense to be able to figure out how you build a winning product solution, you know, 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. 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, you know, are, are going to be there. It's just that they're going to become, um, you know, they're going to become more high stakes, uh, 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. Uh, and so sort of early stage PM, then it's really all about execution and…

AI assessment note: “I think at the very beginning, it's all about those core PM fundamentals, right?”

Q anywhere near as well as you do, and so it might be quite a base strategy to you. Obviously it would be because I don't know the business nearly as well as anyone in Calendly, 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? Do you see what I mean?

A Absolutely. So I would, um, most of the competency questions, typically we'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, uh, which sort of puts you on the same footing as the candidate of, you know, neither one of us necessarily know, know much or experts in this space. Um, but you sort of use a hypothetical. So I think the, the, um, this set of the, uh, interview process all about, uh, should all about be drawing on your past experience and, 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? Uh, 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, the, 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 …

AI assessment note: “drawing on your past experience and, and sort of using hypotheticals”

Q Speaking of product strategy and decisions, and this is the final one, I promise, because I could talk to you all day, but can you tell me a story of a product decision that you made that was a mistake, and what did you learn from it?

A Yeah, um, so when I was at Box, uh, so I went to Box after, um, my startup, and back in And had the opportunity to actually build our first kind of add on products or sort of our transition from single product to multi-product portfolio. Um, and so we, you know, we did a ton of customer diligence. We did a bunch of market analysis. We had, you know, a very clear prototype. We validated with customers. We felt pretty, pretty, um, confident that there was going to be sort of quote unquote product market fit with this new product. Uh, and so we made, Very aggressive revenue projections around what we believed we could deliver out of this new product in year one, in year two, in year three. Um, and so year one, we went to market, lots of excitement from our sales team, lots of excitement from our customers. Um, but we missed, you know, sort of those, those internal projections around, around what we believed we could deliver to the business, uh, pretty substantially. And there were really a couple of reasons, learnings from that experience. By year two and by year three, we had caught up to our projections. So it wasn't a matter of missing the mark In terms of the product decision, the lesson for me was really more around bringing new products to market within an organization where you already have a very successful core product. Uh, two things about it. One, it always takes much l…

AI assessment note: “the lesson for me was really more around bringing new products to market”

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

A Yeah, I think you sort of get to a place with your first product where, um, you know, it's very clear that you found product market fit, right? Your target customers are actually using and buying and talking about your product. Um, there's a lot of definitions out there of what product market fit is. I think that, you know, sort of when you see it, you feel it, uh, and you know, it's there. Um, and I think you have to be really diligent of, of even once you've found product market fit, really doubling down and scaling the existing product for quite some time period. Um, and then you sort of get to a place where, okay, things are pretty repeatable. Things are pretty predictable. Growth is, you know, uh, something that we can really model out. Now let's actually start to think about what the next product is to build. Um, and, and I think actually maybe one of the bigger mistakes that companies make is doing that too late. Um, 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 as they find themselves behind the eight ball, uh, having not actually invested early enough, or at least laid the foundation for what they might want to do, um, as their second product.

AI assessment note: “Things are pretty predictable... Now let's actually start to think about what the next product is”

Q I think. And so when we think about this discussion, uh, so many founders listen to the show and, uh, you're going to be a hypothetical angel in my company. Thrilled to have you. Thank you. Uh, wonderful. Um, uh, 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?

A Yep. 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. So pre-product market fit, you know, uh, founders usually doing most of the product management, working with directly with the engineers, getting things built. Um, then usually, you know, you sort of find product market fit 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. Um, 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, you know, things are working well, we're humming, uh, then your job as the product leader becomes not just executing the founder's vision, but how do I keep predictability? How do I create repeatability? How do I start to hire, um, you know, a team and start to make this machine move faster, uh, to continue to essentially execute. And then I think you hit another phase, which I'll just call kind of hyper growth or late stage where A little bit of what we've already talked about. You have a product and it's humming, and now it's time to, to open up new growth levers. So you're talking about new produ…

AI assessment note: “corresponds to where a company is in their growth trajectory”

Q So what would you do differently as a result?

A There's two things. One, I would be more realistic with my expectations and the modeling that we did around when we could expect, uh, the actual revenue. But I think more importantly, uh, I would have, 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, you know, when we bring this, this, this new product to market, we're also going to do X, Y, and Z to ensure that the sales reps are incentivized. Um, to actually sell the product and, and, and actually allow us to, um, you know, potentially hit our, our target for year one.

AI assessment note: “There's two things. One, I would be more realistic with my expectations”

Q 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?

A I don't think they have to. I think that it increases the likelihood that you'll be able to do it faster, uh, and that you'll be able to deliver additional value to the same set of users if you do. Um, uh, you know, and I think oftentimes, you know, You, 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, you have something that you're taking advantage of. And so I think usually they, 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.

AI assessment note: “I don't think they have to. I think that it increases the likelihood”

Q 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, RBAC, security enhancements, everything that comes with it. This sounds awful. Why, why would you do that as a product person? And from the product perspective, not an org perspective, what needs to really change?

A I think there's, there's two answers to that question. I think the first is you're absolutely right. There's blocking and tackling you have to do from a security and compliance and, uh, sort of scale perspective to help support larger and larger customers. And that's, you know, that's just sort of work you have to do. Um, 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. Uh, 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? Uh, how do I think about going deeper and helping to solve the needs for, again, this recruiter 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, um, and, and actually really more interesting, even though, yes, there is the blocking and tackling you just have to do, uh, in order to be able to sell into the, to the enterprise.

AI assessment note: “from a product perspective, it becomes more dynamic, um, and, and actually really more interesting”

Q Can I ask the other one is like, it's probably again, I'm peppering you for questions here. Is product art or science? I'm always like edging between the two and I'm never really sure where I land because it's so back and forth. How would you think about that?

A Yeah. 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 you people using the product today? Where do they have challenges when they're using it? Uh, who are 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. I think when it comes to, and so 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. Uh, and there's this definition of sort of quote unquote product sense that, that we talk about a lot, which is just sort of this combination of, you know, curiosity and creativity and intuition around how to solve a problem. Uh, and that to me is something that's, that of course you can still use some science. You'll do discovery. You'll talk to customers. They'll get input, but at the end of the day, there's a l…

AI assessment note: “science can be very well applied to that first part... becomes much more art”

Q operators, um, and the operators are good at process repeatability, um, 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? Being CPO of, you know, a hundred person plus product team or whatever that is, do you have to lose that craftsmanship?

A Absolutely not, and the best product companies out there find a way not to. Um, I think, Maybe, uh, an important part of that formula is one, what's the role of the founder? Uh, typically founder CEO, but what's the role of the sort of the founder who, who sort of started with the product vision? Uh, and this is where I think, um, 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 skill set 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 that vision. Well, then you're just going to clash or, you know, or opposite, right? You, you really need someone who's going to bring that vision. The founder or CEO has moved into a much different role, but you go hire what you just described as sort of the, 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, who's, who ha…

AI assessment note: “Absolutely not, and the best product companies out there find a way not to.”

Q So when we think about the hiring process, again, I'm a young first time founder, but my company is fantastic. Um, and you're an angel, so lucky. Um, 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?

A Yep. 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 or your company? This can vary company to company. Um, and as we've already talked about the definition of what product management is, uh, even something that is Uh, 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? Um, and so once you sort of have at least a general framework for what you're looking for for candidates, then it typically goes through sort of a three part process. The first is usually the hiring manager phone screen. Uh, or the first sort of meeting with the hiring manager. This is typically where you want to really understand more deeply their background and their experience and their skillset. Uh, and maybe even most importantly, their interest in the role. Uh, and if you can get ahead of, you know, sort of wasting time across the whole interview process, just to find out that, you know, really this person's interests don't really align with, with the role. You'll…

AI assessment note: “then it typically goes through sort of a three part process.”

Q anywhere near as well as you do, and so it might be quite a base strategy to you. Obviously it would be because I don't know the business nearly as well as anyone in Calendly, 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? Do you see what I mean?

A Absolutely. So I would, um, most of the competency questions, typically we'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, uh, which sort of puts you on the same footing as the candidate of, you know, neither one of us necessarily know, know much or experts in this space. Um, but you sort of use a hypothetical. So I think the, the, um, this set of the, uh, interview process all about, uh, should all about be drawing on your past experience and, 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? Uh, 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, the, 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 …

AI assessment note: “you let them use their experience to, to help describe to you”