20Product: When to Hire a CPO, The Three Different Types of CPO, How To Know What You Need, How To Structure the Hiring Process, What Are the Must-Ask Questions, What Tests and Case Studies Should Be Used, How Should Their Compensation Package Be Structur

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. Before Calendly, Annie led Glassdoor’s product vision and user experience, managing a 70-person product and design org. Shreyas Doshi is an investor, advisor, and all-around product OG. Most recently Shreyas spent over 5 years at Stripe where he was Stripe’s first PM Manager and helped grow the PM function (from ~5 to more than 50 people). Before Stripe, Shreyas was a Director of Product Management @ Twitter. David Lieb is one of the product OGs of the last decade. As the founder of Bump David pioneered how over 150M users shared data, contacts and more before the company was acquired by Google. At Google, David took this one step further by creating Google Photos. Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for Hewlett-Packard, Netscape Communications, and eBay. Aparna Chennapragada is the former CPO @ Robinhood, revolutionizing consumer finance with commission-free investing. Prior to Robinhood, she spent an incredible 12 years at Google, most recently as VP and GM for Consumer Shopping and also as the lead AR and Visual Search products. Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and one of the most popular newsletters on Substack. For the last 7 years, Kayvon Beykpour has been at Twitter where he led all of the teams across Product, Engineering, Design, Research, and Customer Service & Operations. Kayvon came to Twitter through Periscope, the live broadcasting app he founded that was acquired by Twitter in 2015. Scott Belsky is an entrepreneur, author, investor, and currently serves as Adobe’s Chief Product Officer. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. In 2006, Scott founded Behance, and served as CEO until Adobe acquired Behance in 2012. In Today's Episode on How to Hire a Product Manager, We Discuss: 1.) When to Hire Your First PM: What are the core signs that the founder must delegate and hire their first PM? What are the first things that are breaking when you do not have one but need one? How does the timing of the first PM differ when comparing B2B vs B2C? 2.) What is the Right Profile: What should founders look for in this first PM hire? What traits make the best? What are the biggest red flags in the personalities and styles of potential candidates? Should they have experience in the product domain they are entering? What are the single biggest mistakes founders make when analyzing the resumes of potential PM candidates? What should they look for in their resume? 3.) The Hiring Process: How To Hire a Product Manager How do we structure and run the hiring process for this person? What tests can we do to understand if they have the skill set we need for the role? How do we structure a hiring panel to make this process more effective? What are the biggest mistakes founders make in the hiring process for PMs?

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

• 0:00Speaker 00

  One of the patterns is the three types of product leaders and they are the operator, the crafts person and the visionary.

• 0:07Speaker 01

  Most of the really strong PMs that have emerged, say, on the Google Photos team, came from backgrounds with no experience in this domain. I would probably go so far as to say that it's anti-correlated with the top performers.

• 0:18Harry Stebbings?

  Welcome back to 20 Product. This is the monthly show where we sit down with the best product leaders to unpack their tips, tactics and strategies to scaling the best product teams today. And today we answer the core question in scaling product. When's the right time to hire my first PM? What are the signs we need that we need to hire them? What should we look for in this person? How do we structure the hiring process? And how and what should we test for? Now, dropping this knowledge in today's episode is product leaders from Adobe, Airbnb, Stripe, Google, Twitter. And this episode is one to bookmark and keep. So many incredible nuggets of wisdom in here. But before we dive into the show today, I need your help. I need your input on the 20 VC Miro board as I'm booking new guests that we should feature on the show in 2023.

• 1:01Harry Stebbings?

  Now, this is the only way to make suggestions. Head on over to miro.com/20vc and leave your suggestions with digital sticky notes or comments. That's miro.com/20vc. And Miro actually sponsored this episode. For those of you that have not used it before, it's this incredible tool that I think is truly game changing. Just ask the 1 million plus people who sign up for Miro every month. It's a visual collaboration platform packed with the right tools, tech and templates to grow your idea, your product, your vision at scale. Miro acts as a single source of truth across teams. That means you can get buy-in much faster from teams like marketing, engineering, sales, product, basically anyone who needs to have a say to make growth projects grow.

• 1:46Harry Stebbings?

  And even though it seems like a simple digital whiteboard, it's so much more. Hashing out a sound acquisition strategy, brainstorming Miro, rethinking your sign-up flow, using Miro's user research templates, quickly visualize team structures on a Miro board. However you need to grow, Miro can help. We use Miro all the time to brainstorm future shows, vote on potential guests and leave notes for the rest of the team in our own time. Check it out again at miro.com/20vc to submit your guest suggestions. And I'm really excited about this next sponsor. This episode is brought to you by Mixpanel, offering powerful self-serve product analytics. You know, something we talk about a lot on this show is how startups can build the best possible product.

• 2:28Harry Stebbings?

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• 3:11Harry Stebbings?

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• 3:53Harry Stebbings?

  to boost your conversion and retention rates by making authentication as frictionless as possible. And Stitch have raised over $100 million from the likes of Coto, Thrive, Benchmark, and Index. And their customers range from individual developers to the fastest-growing companies in tech like Bitcoin.com. And get started today with $1,000 in credits. Sign up at stitch.com/20product. That's stitch, S-T-Y-T-C-H.com/20product.

• 4:29Speaker 00

  You have now arrived at your destination.

• 4:32Harry Stebbings?

  Now, we're going to kick off the show today with Shreyas Doshi. Shreyas is an all-round product OG. Most recently, Shreyas spent over five years at Stripe, where he was Stripe's first PM manager and helped grow the PM function from five to more than 50 people. What are the three different product leader personas that I should know about when entering this hiring process?

• 4:52Speaker 00

  One of the patterns is the three types of product leaders, and they are the operator, the crafts person, and the visionary. What is really important is there is no one right answer, first of all. It really depends. But the second thing is that it's important to recognize that it's not like a certain person can only be an operator. They can wear each of these hats. So you can think about them as hats, but still people have a primary hat, and that's the hat that makes them most comfortable. That's the hat they would rather wear. But the operator is excellent at scaling teams, driving cross-org alignment, and unblocking execution. And the operator's superpower is communication. On the other hand, one of their challenges is actually original product insight. So this is very important to remember.

• 5:35Speaker 00

  There are oftentimes there are operators who just have amazing resumes. They've scaled companies and products extremely well, whether it's larger companies or mid-sized companies. But despite all that experience, they do not have the ability to come up with really original product insights. This is where often things go wrong with CPO hiring or VP product hiring. Sometimes your situation is such that you do not yet need an operator. Eventually, almost everybody starts needing an operator in their head of product role, but you don't yet need one. But you bring somebody on with the expectation that our business is going to quadruple at some point. So at some point, we're going to need somebody like this. So why not bring them early? But the problem is now this operator starts operating

• 6:18Speaker 00

  instead of helping you get to a better position with your product market fit. That requires original product insight. And without much help, the operator is not going to be able to do it on their own. So that's just an example of where things go wrong.

• 6:31Harry Stebbings?

  When does that transition happen from not needing the operator to needing the operator?

• 6:37Speaker 00

  It is near Extremely impossible for an operator to bring your product to product market fit. But once you hit product market fit and as your product starts scaling, as the cross-organization complexity increases. Now, what happens is in addition to managing the product, you also have a real big organization to manage. Oftentimes, it's cross-team, right? Like, you're not owning everything. And that's where operators are tremendously valuable, because they are extremely skilled at orchestrating cross-organizational action. They're extremely skilled at communication to make sure that everybody's aligned. They're fairly skilled at setting targets, setting goals, and creating a sort of a rhythm in terms of how you launch things in this complex internal environment.

• 7:22Speaker 00

  So really, that is the point. But at some point, it becomes very clear that you need an operator, and then you need to go find one. What's the crafts person in terms of like that profile then? Walk me through that one. So the crafts person is excellent at defining products and strategy and mentoring other product people. And their superpower is product insight. The crafts person is able to translate an extremely ambiguous goal or an extremely ambiguous vision into concrete product that has a very high chance of winning. That skill of translating something high-level and ambiguous to actual product, the pixels, the customer support experience, the interplay of the various things that need to happen to make a product and a business successful, they are able to translate that really well.

• 8:06Speaker 00

  Again, their superpower is product insight, but they're not excellent at dealing with large orgs and its taxes, right? Because any large org comes with all sorts of taxes that you have to deal with. They just don't enjoy that. They love spending time with the team and users. It's interesting, operators, they love spending time with their peers, other functional heads and company execs and the board. Whereas as crafts people, absolutely love spending time with users and customers and the team. And they get really excited about product deep dives. And, oh, let's walk through this flow and how can we make it better? So that's the crafts person, is a very essential ingredient in any team. Whether it's a product leader or even individual product managers, you need these people so that you can translate something ambiguous into. Do something concrete.

• 8:49Harry Stebbings?

  If I'm hiring my first CPO, head of product, whatever we want to name it, but senior product hire, is that profile the profile I want to go for?

• 8:58Speaker 00

  That is a reasonable default, especially if you're early stage, say perhaps pre PMF or just about reaching PMF, then crafts person is of good default. When I go through these kind of sessions with founders, one of the core things I ask them is like, why do you want to hire a product manager? What is it that you want this person to do that you are doing right now? Sometimes, Harry, the answer is I want to delegate a lot of the operational work. I want to delegate figuring out how the sprints are going to work or figuring out how customer support is going to get impacted by this new product feature that we are launching. Those types of things I want to delegate, but I still feel like I need to own the core product insights

• 9:42Speaker 00

  and some of the definition of the product. In those cases, you may want to bring a sort of like a mid-level or a junior operator type person and kind of delegate those operations while still holding on to the visionary and crafts person hat yourself as a founder. So that is possible, but the default crafts person is a good place to start.

• 10:00Harry Stebbings?

  Before we move into the visionary, you mentioned like the cross-person struggles with the scaling product team. What are the first things to break, sure, ass, in a scaling product team?

• 10:09Speaker 00

  There are two core things that tend to break across most situations. One is within the team. As a team grows, a large part of your role as a leader, you're basically a repeater. You just have to keep repeating the same thing. If you're managing a team of 25 people, you can have a sort of personal relationship, some amount of trust, some amount of like just mind meld with a group that's say 20 or 25. Now your team is 50 people. It's impossible to create that mind meld. So you need to change your approach. Now, instead of relying on one-to-one or one-to-few interactions, you have to rely on one-to-many interactions. But people don't remember as much as we think they remember. So you have to keep repeating the vision, the goals, the strategy.

• 10:54Speaker 00

  That becomes a really important part of your role. A crafts person can. Do this, but as the team scales, a crafts person, most crafts people don't enjoy that. So that's one thing that kind of starts breaking internally for a crafts person. Externally, so outside of the org, what ends up happening is as the business scales, there are other parts of the business, other departments like sales and support and BD and marketing and various other parts of the organization begin relying on you. And you begin relying more on them as well. You're no longer kind of self-sufficient and scrappy. And there are a lot of alignment issues. There are a lot of dependencies that you need to resolve. When you reach a certain scale, that becomes an extremely large part of a product leader's role.

• 11:38Speaker 00

  So that's the part that starts breaking outside of the team. What is the profile of a visionary? Among these profiles, the visionary is the most rare. The visionary is excellent at big picture thinking, inventing what's next. And their superpower being that they can see what others cannot see. One of the challenges with a visionary is that a visionary finds it difficult to translate that big vision, which by the way, again, by definition, very few people can see that vision. Even many crafts people cannot see that big vision. A visionary finds it hard to translate that to concrete product steps. Like, okay, so I want to do this. I want to revolutionize, I don't know, spreadsheets. And I have a certain vision in my head of how that is supposed to happen. But what is the first step I take? What is the next step I take?

• 12:22Speaker 00

  And what's the step after that? That is where a visionary works very well with a crafts person. Because a crafts person can translate that into concrete steps. And again, there are many visionaries who are also crafts people. And I've worked with many such folks. So they can do that job, but only to a point. These really great visionaries, they often find it hard, not always, but they often find it hard without the support of crafts people and operators to do it consistently. Should the founder not be the visionary and the CPO not be the crafts person? It's usually one of the founders that's the visionary. Perhaps, you know, there's another founder that's more like an operator. And maybe even a third that's more like a crafts person. But typically, there is one founder who's the core visionary, who then takes ownership of the product.

• 13:07Speaker 00

  And sometimes Wears the crafts person hat and like I said, they can be fairly good at it to kind of translate that vision into certain kind of product manifestations. But at some point, it becomes harder for them like because once you start getting users and once you start getting usage. What ends up happening is users are pulling you in many different directions. The visionary has a very clear view of the future, but being responsible people, they also now take into account user and customer feedback. And that can get confusing at times, even if it's not confusing for them, they may find it hard to kind of like bring the team along on like, okay. Given all this kind of conflicting feedback and this plethora of ways in which we can take the product. Here's what we're going to do as step one, step two, step three. Here's how we're going to actually build out the product. These are the flows that matter. These are the flows that don't matter.

• 13:50Speaker 00

  That's when whether it's a CPO or a VP product or even a director of product or an individual product manager. Crafts person becomes a great asset for a visionary.

• 13:59Harry Stebbings?

  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 70 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?

• 14:20Speaker 03

  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 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 got to 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. And 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? How do I start to hire?

• 15:01Speaker 03

  Team and start to make this machine move faster to continue to essentially execute. And then I think you've 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 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.

• 15:32Harry Stebbings?

  Incredibly rogue forward suggestion. I've, I've seen the different profiles from interviewing the best CPOs in the world. And there's like visionaries early, and I think Shreyas Doshi says this, well, 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?

• 16:04Speaker 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. 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 strong on that vision, well, then you're just going to clash or opposite, right? You really need someone who's going to bring that vision.

• 16:47Speaker 03

  The founder or CEO has moved into a, 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.

• 17:12Harry Stebbings?

  So when we think about the hiring process, 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?

• 17:20Speaker 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? 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, then it typically goes through sort of a three-part process. The first is usually the hiring manager phone screen. 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

• 18:05Speaker 03

  just to find out that really this person's interests don't really align with the role. 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, 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. 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.

• 18:48Harry Stebbings?

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

• 18:54Speaker 03

  For me, I'd 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 in 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

• 19:39Speaker 03

  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.

• 19:58Harry Stebbings?

  Now, we're going to move to David Lee, founder of Bump and has run Google Photos for the last 10 years. How do you structure your hiring process for a product team? What is the process?

• 20:09Speaker 01

  Well, if you're early stage, your product team maybe is one person, right? Maybe you're hiring one PM. This is another meta mistake is people think like, I've raised my seed round, I have $4 million, like, let's go hire a team of 20 people. That's what I see all my cohort members doing. That's probably the wrong thing to do unless you really have product market fit already. But let's assume things are on fire, like, oh, my God, we've got to build all these things. Like, great news. I would say at the early stage, the number one thing I would filter for and find some products that you think are good and some products that you think are bad, ask them about them. See if they've ever gotten to the point of thinking about why a product they love is great versus why a product that they don't love is bad. And can they explain it to you? Do they have an opinion on it? These are things that are very squishy. It's very hard to like, how would you like,

• 20:54Speaker 01

  write a multiple choice test that would test that? It's very difficult. But these are the things you're looking for because they show that the person has like thought from first principles about why a thing that they see is true in the world is true. And the why is what matters. And the skill of asking why and learning why or figuring out why has the number one skill for building early stage companies because that's what you're doing all day long. Why is this working? Why is this not working? How do we do more of the thing that is working?

• 21:18Harry Stebbings?

  When do you think about bringing in CPOs? If we're a scaling company, I often see the transition required. When would you advise founders on now you need a CPO slash head of product, not just jack of all trades?

• 21:28Speaker 01

  Again, most people do this probably too early. So. That's like the common theme here. So I made this mistake myself. At Bump, we got to like, maybe it was 30 employees. All of our vanity metric graphs were like going way up. We were feeling really good. And I thought our company is gonna need to like figure out our business model eventually. We're gonna need to keep scaling and hiring. I'm gonna have to do more fundraising. I better hire a product lead to take over from me and I'll go focus on those other things. And I did. He was awesome. And then we realized, oh, actually, we have not really solved product market fit. Sure, we have a lot of people who use our product, but like, we can't figure out a way for them to pay us. We can't figure out anybody else in the world who will pay us for access to those users in some way. So really, we don't have product market fit. Whoops.

• 22:11Speaker 01

  And I realized the success or failure of my company actually has to do with what this person I just hired is gonna go figure out for me. Generally, that is a very dangerous place to be, where the founders or the CEO of the company is not working on the most important problem for the company's success. I just found at some point that I need to be doing that. It's my responsibility for this company to be successful. I better be working on this. And now all of a sudden, we have two people who wanna be top person on product. Dave made a mistake. I was wrong about when to hire this thing and we parted ways and that was the right call for the company.

• 22:42Harry Stebbings?

  You said there about kind of the mistake. Honey Pearl from Callanly, CPO at Callanly, said on the show the other day that the biggest mistake that founders make when hiring CPOs is actually they have misaligned expectations. And they bring someone in, but they still kind of wanna own it and they don't really.

• 22:54Speaker 01

  Exactly that. I think the other piece of it is people wanna hire people like them. When you're hiring the top product lead for your team, if you plan to be around for a long time, you probably don't wanna hire someone exactly like you with the same set of skills. As an example, on Google Photos, when we grew enough to where I needed to hire someone to run the product team, I very explicitly wanted someone who had a complementary set of skills. What are the things that I'm uniquely bad at? Let's find someone who's world-class at all of those things and they will like really plug a big gap in our team. That's the way you should do these things.

• 23:26Harry Stebbings?

  I had sure I asked Oshie on the show as well, and he categorized three different product leaders. He said there's craftsmen and women, there's visionaries, and there's operators. And I think the most damaging one that I see is the operators. And what I mean by the operators is the Series C professional CPOs, who come in and put a lot of process in place and actually do very little. And they like talking to other CPOs and they like talking to the board and feeling important. Do you agree with that? How do you prevent getting that operator, which actually just brings process and delays?

• 23:58Speaker 01

  Yeah, 100% agree. I would say like the number one failure mode when people hire product leaders is they over-index on previous scale. How big of a team have you previously managed? Or tenure, like how long have you been doing this? What experience do you have? Do you have experience in our domain? It turns out that if you're the median PM in the world, you're like middle of the stack, not good, not bad, you're just median. If you stay in the game long enough, you will be that person. By definition, almost, right? If you last long enough, you will eventually lead a team of 25 PMs. But you're not actually good necessarily, you're median. And it's very dangerous to hire those people. You've heard this saying before, but like A players hire A players and B players hire C players. It's totally true. It happens like literally all the time. I watch it happen.

• 24:41Speaker 01

  Once you hire that B player to be your lead, like bye bye, your team is gone. Like the best people on your team are not going to want to work with that person. So how do you avoid it? I think you gotta retain this ability to be either a craftsman or a visionary, hopefully both. Because those are the people that people want to follow. They want to listen to what they're saying. They want to work with the people who want to work with that person. I think it's incredibly valuable. Yet founders think I better hire this experienced person who knows how to do this. But turns out they don't actually know how to do it, no more than you do.

• 25:10Harry Stebbings?

  Is there ever a time for an operator? When you are a smart sheet or an Anaplan? Or name your kind of quite non-creative SaaS enterprise product respectfully?

• 25:21Speaker 01

  Yeah, yeah.

• 25:21Harry Stebbings?

  Is there a time for what?

• 25:22Speaker 01

  Yes, but there still must be a product visionary and a crafts person. You gotta have somebody on the team who's doing that role. It's totally fine if that person is the founder CEO or the co-founder who's focusing on product. And if you're hiring an operator to like run your team, which those people are incredibly valuable. You can't really operate at scale without somebody who's good at that. But you should not confuse that with who is the visionary? Who's the person, you know, like leading the charge on what we're going to build next? Who's the person that reinforces the culture that we want at the company day to day? That person must exist. It's fine if it's not the chief product officer. It just needs to be somebody.

• 25:57Harry Stebbings?

  Final one on the hiring process. Do we need to hire people who've built products like the product we're building before?

• 26:02Speaker 01

  Yeah, in my experience, most of the really strong PMs that have emerged, say on the Google Photos team. Came from backgrounds with no experience in this domain. I would probably go so far as to say that it's anti-correlated with the top performers. The top performers tend to come from some strange background. I think one of the folks you talked to on our team joined Google as like a salesperson. And now they're a PM running like a big chunk of Google Photos. And again, I think it gets down to this like self-selection for ambition, like a chip on your shoulder. These people want to prove that they can do this, that they can win. And those people tend to work harder, they tend to like understand the customer more, they go the extra mile. And these are the things that separate success from losing.

• 26:40Harry Stebbings?

  I'm so enjoying this. What's the difference in good and great in those PMs?

• 26:44Speaker 01

  I guess it comes down to two things, the ability to really understand the user very deeply. And then the ability to craft creative solutions to those problems that you find. Those I think are the two core parts of the job of being a PM.

• 26:57Harry Stebbings?

  I loved having David on the show, but now I'm thrilled to welcome Marty Kagan, one of the OGs of product and product management as the founder of Silicon Valley Product Group. When is the right time to hire your first product people?

• 27:07Speaker 04

  I'm a big believer in the founder as the product leader. I personally never invest in a startup unless at least one of the founders is a proven product leader. Now, of course, the equation, the calculus is a little different if neither or none of the founders are a product leader. First of all, I don't have a lot of confidence in that company. But second, you're going to have to bring products expertise on much, much sooner. But if we can assume in this discussion, we have at least one founder that's a proven product leader, then it actually becomes quite clear. And honestly, it's a function of the number of engineers more than anything. That's the heuristic I use. And that's because at a certain point, there is no way for that founder

• 27:50Speaker 04

  to be close enough to all of the engineers to be able to make the daily decisions on the product that founder needs to make. Partly this depends on just how many hours is this founder willing to invest in this stuff? But realistically, once you get past about 25, 30 engineers, the teams are saying, I can't get enough time with the founder. I just can't get enough time. We're going too slow. We're waiting. We're making bad choices or no choices, which is worse.

• 28:17Harry Stebbings?

  That seems like an awful lot of Engineers, twenty five before you make that hire.

• 28:22Speaker 04

  Realize it's not like twenty five flat engineers were all are considered equal. What they are, they're naturally going to group around product teams. If you have twenty five engineers, you've probably got a minimum of three, probably four, five product teams. Each one of those will have a very senior engineer. It's those people that have to have that very close relationship with the founder. That tech lead, of course, is talking in detail with all the other engineers about how they're going to divide and conquer on the work.

• 28:54Harry Stebbings?

  How do I structure the hiring process for them? How many meetings do we have? What do I want to achieve in each meeting? Can you help me literally from scratch?

• 29:03Speaker 04

  Probably the most important, actually. Let's talk about what you really need. What kind of person are you looking for? Is it literally just your capacity is out? Or maybe you're much more the visionary and you need somebody that knows how to make this machine work a lot faster. These are some pretty different responsibilities that you're talking about. We want to be very clear on the kind of product person that you're really looking for. And then we can get to work. Yes, for sure. Most companies, in my opinion, don't do a very good job on the whole hiring process. They're just very random. Another big thing we need to talk about is what is your philosophy on this? Would you rather hire, say, university graduates and develop them into the kind of people you need?

• 29:47Speaker 04

  Or do you say, no, I want people that are been there, done that, and I'm willing to pay a lot more, but I'm paying for that experience? Both of those can work. What's great about startups? The biggest reason somebody great would join your company is because of your product vision. You are trying to do something that inspires them. Look at all the people that go work for Tesla or SpaceX despite crazy everything because they are so passionate about what those companies are trying to do. This is our number one tool for attracting strong product people is having a very inspiring and compelling vision. Here's the thing, though, on hiring that's most important.

• 30:28Speaker 04

  Important if you decide for whatever reason you're gonna hire junior people, then the worst thing you can do is do that and not have somebody in place to develop them. If you just hire junior people and they have no coaching on an ongoing basis, you're just throwing good money after bad. That's exactly what happens in so many companies. So the prerequisite for hiring junior people, and I want to be clear, I love this model. And this is the most scalable model I know. Look at Google, look at Apple, they do a ton of this, but they have the mechanism in place. Microsoft too, the mechanism in place. Their managers know their number one responsibility is to coach and develop these people.

• 31:13Harry Stebbings?

  Let's run with this though. We've gone for that model. How do I know the best ones? And how do I structure an interview process to determine the quality of these young, but potentially brilliant candidates?

• 31:25Speaker 04

  If you're hiring experienced people, that's one interview. If you're hiring by definition inexperienced people, that's a very different one. You're looking, and obviously when you're looking for experience, you're looking for whether they can prove to you they've learned about the business, they've learned about customers, they understand the techniques. To me, that is much more straightforward. When you were hiring on potential, then you're making a bet on really more innate traits. And then you're looking for things like, is this person got a strong work ethic? Does this person have a strong sense of curiosity? Is this person that gives up very easily when they run into roadblocks? There's a lot of ways to test. I'm not a fan, by the way, of tests in terms of people will have these assignments.

• 32:10Harry Stebbings?

  Why not out of interest? Cause that's like a tangible thing that people like to do.

• 32:14Speaker 04

  In my experience, they're not very indicative of what you're really looking for. And let me put it this way, I still haven't found that test that I think is any good. It is true though, that the risk for an inexperienced hire is higher. I always tell the, first of all, I tell the founder, please don't do that unless you have like a director in place who knows it's their job. To coach and develop those people. Don't do it, otherwise you're just setting them up to fail. But if you've got that person, then I tell them that they've basically have three months to get those people to competence. That's what it usually takes is about three months to get them to competence.

• 32:56Harry Stebbings?

  I had David Lieb on the show, former product lead for Google Photos. And he said, actually, he had better experience with people who had never done that domain before.

• 33:05Speaker 04

  He's absolutely right. There has always been a debate in the product world. Do you hire people from the domain? Or do you hire product people based on product potential? And expect that they can learn pretty much any domain. I am squarely on the side that I think he is. My evidence for that is just look across our industry, across time, that all the innovative products, almost all of them, came from people and teams that had no real domain experience. You probably know Shri Ash Doshi. The way he phrased this, I give him credit, I love it. I've shared it with lots of people. But one of the things that's critical about product

• 33:46Speaker 04

  is to be able to understand the difference between domain expertise and domain dogma. And it is very hard when you grow up in a domain to be able to know the difference. You're too close that way. That's my theory that explains why is it that so often the innovations come from people outside of that domain. I'm a big fan of hiring for product people. And I expect them to be able to learn the domain. That's part of the three months. I know some people that came from the domain that are rock stars. It's just that, for the most part, I would rather have somebody with good product skills that I know can learn what they need to quickly.

• 34:28Harry Stebbings?

  I mean, no one better than the one and only Marty Kagan. But now I'm so excited to welcome a dear friend in Lenny Rzitski. He spent an incredible seven years at Airbnb and now has one of the best newsletters on product. You can check that out in the show notes. When is the right time to hire a product manager?

• 34:44Speaker 05

  My first piece of advice always is you should wait longer than you think you need to.

• 34:48Speaker 05

  often have this dream they're gonna find this amazing person they're gonna agree with them on everything they're gonna know how to build incredible product and they could just kind of like delegate this but it turns out that's rarely the case usually what actually happens you find this person you as a founder you still have really strong opinions about what to build and you've been doing it for a long time and then there's like the team building and so this PM just becomes this middle layer between you telling them it really think we should build this and they're like do I have any autonomy do I have any way that I can actually inform what we're building you're just telling me what to build and they're just like telling engineers what to build and it becomes a really hard job for a lot of PMs a lot of times you the founder has a bad time with that too so just like default advice is wait longer than you think but the three things that have founders have told me are kind of signs that they need to hire a PM one is they're experiencing a bunch of bottlenecks frequent bottlenecks where engineers or designers are just like block waiting for them to make a decision waiting for them to make to review a design so if you're finding there's just like your team is blocked and you need somebody to unblock them that's a sign you may need a PM another is just frequent misalignment timelines are not on people like design engineer for example are not aware of oh we're trying to hit this date or they're misaligned on priorities or they're misaligned on the strategy where people are just not in sync and that's what PMs are really good at and so that's a time where not PM could come in and help you a third bucket is really interesting and this happened at a few companies and that's where you have an opportunity to explore a new idea and a new direction kind of like a new little side opportunity as a founder you just don't have time and you want to find kind of a mini CEO to take that on so as an example Zimride to explore the idea of Lyft hired their first PM and his job was go explore this idea of Lyft for us Snap and Twitter from what I understand both hired their first PM to explore monetization on the platform so that was their first PM

• 36:25Harry Stebbings?

  I love that as like a startup CEO for an ancillary business I'm entering the hiring process now and lucky me you're helping me so when we think through this how do I structure my hiring process for the product team Lenny actually just like break it down for me like meeting by meeting because I have no idea what to ask and what to expect

• 36:45Speaker 05

  yeah totally so there's a lot of ways to do it unclear exactly what the best way to do it but the way I like to approach it and it works is you basically bring a candidate in for a whole day try to break up the interview process to a project at the beginning of the day and then a bunch A one-on-one interviews the second half of the day. And before I get into those two, just like broadly, the things you want to be looking for in a PM. There's kind of these five key skills. Focus on their execution skills, their collaboration skills, their just broad leadership skills, their vision plus strategy, and then their ability to do customer user research and extract customer insights. Five things to focus on. Okay, so they come in, the first thing I like to do is do a little project. And the way I like to approach it is I sit them down and I give them a prompt, I print it out. Here's like a problem that you as a PMer needs to solve.

• 37:29Speaker 05

  It could be like, how do we increase adoption of this feature by 50%? Or how do we grow supply in our marketplace by a thousand percent? That kind of thing. And then you give them some context so they have all the information. Then you give them 90 minutes to sit there and just think about it and put together a presentation or a doc with how they'd approach it. And then they present it to a group of cross-functional team members. And then there's some Q and A and things like that. And the thing you look for there is not they have the best answer and have they come up with the best solution? But how do they break it down? How do they approach the problem? How do they zero in on where opportunity could be? And then just like their gut instincts, what might work. Personally, I hate putting people on the spot with a really hard task. Because as a PM, you don't need to be like on the spot solving really hard problems. You have time to think and process and research. That's why I like to give them time to think about this thing, not just like, cool, design a solution on the whiteboard now, go.

• 38:14Harry Stebbings?

  Again, Lenny's newsletter is absolutely incredible. Now I'm so excited to welcome our partner, Chenopragada, former CPO at Robinhood. And prior to Robinhood, a partner spent an incredible 12 years at Google as VP in GM for consumer shopping. And then also as the lead AR and visual search products. When do I hire a product manager? What are the signs that I need to hire my first product manager?

• 38:37Speaker 06

  So as someone who has actually literally given this advice to someone as of two weeks ago, I'm gonna cheat a bit and share what I said to this founder.

• 38:44Harry Stebbings?

  Right.

• 38:44Speaker 06

  I said two things. One, the biggest risk here is an act of commission, not omission. What I said was you're gonna make a bigger mistake and like it's a bigger negative impact on the company. If you hire the wrong person versus hire the right person. So it's a high leverage hire unless you absolutely, absolutely need it. At the earliest stage, you're the founder, you are the one solving problems for people. So if you outsource that job, that's a big risk. For you, right? You need to live and breathe that problem enough that at some point, if it becomes obvious that there's another person or there's a co-processor that will help and like there's arms and legs that are needed here, yes. But until then, don't do it because you can't think of the problem for people because that is a symptom of a

• 39:26Speaker 06

  bigger problem there, right? And you can't solve it by hiring a product manager. I think the second is, I would say, one of the questions people ask in this ponder, ask to you is like, well, folks say a pre-product market fit, what's the role of a product manager? It is actually something similar to what we just described. I think a really effective, like, hands-on, soft-stage product manager can be the boots on the ground, like actually talk to customers, actually do a whole bunch of research and connect the dots from like what the problems, I translate that to what is the minimum viable product that is being built. And so you need somebody who's just like deeply invested in the problem space. Do not hire a general athlete problem PM is my advice.

• 40:04Harry Stebbings?

  Okay, so we figured out that I need this. How do I structure a hiring process for a PM? Like, what does it look like? What does the first meeting look like? Second, how do I do it?

• 40:14Speaker 06

  I think across the board, there's one invariant, which is you have to decide upfront, what stage are you hiring for, right? So in this your case, if you're saying like it's an early-stage product, the most important factor I would look for is just like the hustle and drive at that stage. At a later stage, and for a different product, the domain experience may matter a lot more. But my bias or my preference is really hire for the hustle and extremely strong, high tolerance for ambiguity and uncertainty. Because like if they get queasy on the roller coaster ride, they're not the right people.

• 40:43Harry Stebbings?

  Okay, so what questions do you ask to tease out the hustle, the drive, the comfortable being uncomfortable?

• 40:50Speaker 06

  So there's two things. One is it's what they did versus what they're saying. Because some folks interview very well, that doesn't often always translate. In fact, actually, like, I think studies have over and over proven for things that are kind of like, there's a lot of practitioner judgment and decision-making discipline involved. The interviewing correlation is only weak. So I would look a lot at kind of the back channel on this person. For example, there are different phases for big companies. Sometimes like there's all these Amazing tailwinds that help companies grow. You know, if you were working on newsfeed and Facebook or search, of course, the web grew with it, mobile grew with it. So you have to differentiate between people who were in the parade versus helped the parade.

• 41:32Speaker 06

  And you certainly have to look for the jerks who pushed everybody aside and somehow got to the front of the parade.

• 41:37Harry Stebbings?

  Now, we're going to move to one of my favorite product lines, Scott Belsky, CPO at Adobe.

• 41:42Speaker 07

  One pushback I oftentimes give to founders is that they should be hiring a product leader so soon. Because as founders and therefore CEOs oftentimes, you think that you should abstract yourself out of every function in order to scale. That's almost true. You know, I think you should abstract yourself out of almost every function, except for the one that is your superpower, that you are the unique person in the world to do. And you should keep doing that as long as humanly possible. Is Mark Zuckerberg still the head of product at Facebook? Is, you know, a lot of these people are still the heads of product of their own companies despite the scale. And it's probably because that is their superpower. They didn't want to fully hand the reins over on something that ultimately differentiated them creating this company over somebody else. So step number one is challenge yourself.

• 42:27Speaker 07

  Should you really be hiring another product visionary if that's you? Or should you hire some people that are more towards the execution side? Help you scale on the accountability as opposed to the vision, number one. I think the second thing is there are different types of product leaders for different stages of a product. You know, some are very comfortable being very design driven, setting a product strategy, a vision, rallying the troops around this, ensuring that the experience is exactly what it needs to be. Whereas others are more of the data driven program manager types who come in. You know, it's always about, here's what we're seeing. We just need to iterate and iterate and iterate this product to make it better and better and better. Those are two different skillsets to some degree. And very few people have them both in equal measure.

• 43:10Speaker 07

  So you have to also think about the type of product leaders you need right now. And then it's about going out and, you know, finding the people that are in the weeds and the products you admire. In terms of actually hiring those product leaders, first of all, I would ask about projects they're really proud of, which gives you a sense of what their values are for measuring the quality of.

• 43:28Speaker 08

  Both a product and a product team. I would look at their products quite a bit. I feel like a product always speaks to the DNA of the team behind it. You can tell who wasn't talking to one another, you know, what the values were, whether there was a designer outsourced or in the room sufficiently empowered, et cetera. And, you know, based on what I see, I would actually ask some questions like, how did the product end up this way? Or why do you do it that way? And just try to get a sense of the reasoning around some of the decisions that were made. So I can better understand, you know, what was going on under the hood there. I would certainly ask about their operating model design and with engineering. You know, it's important to understand how a product leader sees him or herself in the context of these other people. And you get a lot of, a lot of data, you know, from their answers to those questions.

• 44:09Harry Stebbings?

  Now, last but by no means least, I'm thrilled to welcome Kayvon Baipour. For the last seven years, Kayvon has been at Twitter where he led all of the teams across product, engineering, design, research and customer service. Kayvon came to Twitter through Periscope, the live broadcasting app he founded that was acquired by Twitter in 2015. When do you think is the right time to hire your first PM? What are signals that would suggest now is the right time?

• 44:33Speaker 08

  I think one signal is if the team is constantly reacting to what the product needs. Like if you're constantly underwater, the things you end up prioritizing are the things that you learn really late are broken. And you're not feeling like you can be proactive around identifying where the product is going. Then that means that the team is collectively, whatever the current recipe of folks on the team are, doesn't have the right balance of being able to think proactively versus just reacting to things that are happening. And so that might be one good signal of like, well, the division of labor and the time allocation right now just isn't right. So you either need to hire a PM to help think about that stuff or hire a PM to help take on a lot of the work that's like happening so that the right subset of people, founders or that had a product or designer or engineer or whatever can start to think more about that stuff proactively. Because that can be a very dangerous slippery slope

• 45:18Speaker 08

  if the team collectively ends up just being reactive rather than thinking about where the product should be going. So that's one. Two, I think another signal is if the team is getting large enough that there's a lot of communication glossiness around. We're doing a lot of stuff now, but not everyone's clear on what the priorities are. And we're feeling really disheveled and organized just because it's like becoming very expensive to keep everyone on the same page. That can be another signal you need help. Those are probably, I think, the two most powerful ones.

• 45:43Harry Stebbings?

  Okay, so now we have those signals. That's exactly what I'm feeling. We've got it. I need my first PM. Fuck, I've never hired a PM before, Kevon. I didn't know how to structure the hiring process. How do you literally structure the hiring process for a PM? What does that look like in a very granular fashion for you?

• 45:59Speaker 08

  Well, I think the answer to this question should differ depending on the stage of the company. The needs and the skills that I'd look for in a PM at a very, very small company would have some subtle and important differences compared to what you would look for at a company like the size and scale of a Twitter. I think from a skill standpoint, I think at an early stage, a PM needs to be like an infectious truth seeker of what customers need and want. Like, they need to be immersed in your product. And if they're not immersed in your product, they need to have the right skills that will make them the most intimate understander of all things that are working well and not working well of that product. They need to be ruthless about spending time with customers and they need to be just hoovering up as much data points, either qualitative or quantitative, around like what's working and not working at the product.

• 46:42Speaker 08

  That's one. Two, they need to be incredibly comfortable with ambiguity, with kind of doing whatever it takes. Like, the startup mode in particular, I think, there's so many ambiguities of being at an early-stage startup. And it is not an environment where people who need extreme clarity can thrive in. You need to feel comfortable wearing multiple hats. You need to be comfortable doing things as part of your job description that may not necessarily be part of the classical job description. Sometimes you see like folks that have only worked at larger companies struggle with this because they're so used to having a lot of structure and clarity around like, okay, my job is this and therefore my expectations are this. And so I think that having someone who's comfortable with ambiguity and comfortable wearing multiple hats and comfortable doing what it takes

• 47:24Speaker 08

  to scrappily make things work while still having an eye towards making them more durable over time is really, really important.

• 47:31Harry Stebbings?

  What questions or signs would suggest to you that someone is comfortable?

• 47:36Speaker 08

  I think hearing about their experience, what folks have done in their prior roles and what challenges they overcame. Or, you know, even just like asking very high-level prompts, like, what's the gnarliest, most frustrating thing you've had to deal with in your last role? There's some customer problem you had to solve or some team dynamic that was really stressful. And how did you navigate it? Like, people will direct you in very helpful ways. If you give them prompts about their own experience, then that in itself can be very illuminating, right? Hearing them share their recollection of something that they perceived to be challenging for them and how they overcame it, how they navigated it. And I think in those stories, you can learn a lot around A, what they've experienced, and B, how they think about these challenges. So it's always imperfect. Like, you won't really know until you work with someone. But soliciting these anecdotes of their experience can be far more helpful

• 48:20Speaker 08

  than that sort of cookie cutter interview questions that are easy for folks to have good prepared answers to. Do you have favorite questions that you do like to ask in product interviews? I like the really open-ended questions that will solicit the stories, right? Like, asking folks to describe something they've worked on in their last role that they're most proud of. You know, what's something you, like, completely whiffed and failed at? You thought it was totally gonna work, but it didn't. And like, what did you learn from that experience? I think it's important to hear about interpersonal challenges too. Like, you know, what's an area of conflict you've had? Especially for folks that are coming into a larger environment or a larger team. Like, walk me through really gnarly interpersonal conflict you had and like, how did you navigate it? Like, what is one product that you use every day but can't stand using? Like, you wish you didn't have to use it every day, but you do?

• 49:02Speaker 08

  And then also, like, what's a product or service that you adore and love? However big or small it might be, like, why do you love it? I think just getting people to talk about the things they enjoy and the things they don't enjoy and why is helpful. You learn a lot about them. And it's less about judging the thing itself and more about just, you know, hearing how they think about it. Where do you think many founders go wrong or make mistakes when it comes to hiring their first product people? I think the most classical mistake is actually not in making hiring mistakes, but in making the mistake of waiting too long to realize you made a mistake. In my experience, the way harder thing. I've made this mistake plenty of times myself. You just realize that too late, and it takes too long to transition that person out. And that is really, really expensive. It's expensive for the hiring manager.

• 49:45Speaker 08

  It's not doing any favors to the candidate, who will likely have a better chance succeeding somewhere else. And it's not great for the team. Teams who work on really hard problems can either be incredibly inspired by the strength and quality and camaraderie of their teammates, or can be incredibly demoralized by a teammate who's just not the right person for the right role. And that, I think, is the far more common mistake of just taking too long to figure that out.

• 50:09Harry Stebbings?

  I mean, that has to be one of the most comprehensive ultimate guides to when to hire your first PM, how to hire them, what questions to ask. If you'd like to see more from us, of course, you can on 20vc.com or you can find us on YouTube by searching for 20vc. But before we leave you today, I need your help. I need your input on the 20vc Miro board as I'm booking new guests that we should feature on the show in 2023. Now, this is the only way to make suggestions. Head on over to miro.com/20vc and leave your suggestions with digital sticky notes or comments. That's miro.com/20vc and Miro actually sponsored this episode. For those of you that have not used it before, it's this incredible tool. The lighting is truly game changing. Just ask the 1 million plus

• 50:54Harry Stebbings?

  people who sign up for Miro every month. It's a visual collaboration platform packed with the right tools, tech and templates to grow your idea, your product, your vision at scale. Miro answers a single source of truth across teams. That means you can get buy-in much faster from teams like marketing, engineering, sales, product, basically anyone who needs to have a say to make growth projects grow. And even though it seems like a simple digital whiteboard, it's so much more. Hashing out a sound acquisition strategy, brainstorm in Miro, rethinking your sign up flow, using Miro's user research templates, quickly visualize team structures on a Miro board. However you need to grow, Miro can help. We use Miro all the time to brainstorm future shows, vote on potential guests and leave notes

• 51:39Harry Stebbings?

  for the rest of the team in our own time. Check it out again at miro.com/20vc to submit your guest suggestions. And I'm really excited about this next sponsor. This episode is brought to you by Mixpanel, offering powerful self-serve product analytics. You know, something we talk about a lot on this show is how startups can build the best possible product. Relying on gut feelings is an expensive way to find product-market fit, and that's a price many VCs aren't willing to pay. That's why Mixpanel will give you $50,000 in credits when you join their startup program. $50,000 in credits. With Mixpanel, startups find product-market fit faster, helping you take your company from envy P to most valuable player.

• 52:20Harry Stebbings?

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• 53:04Harry Stebbings?

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• 53:48Harry Stebbings?

  That's stitch, S-T-Y-T-C-H.com/20product. As always, I so appreciate all your support and I cannot wait for you to hear next week's episodes.