Kevin Niparko: Big Mistakes Founders Make When Hiring Product Teams | E1066

1. 0:00 – 2:26

   Kevin Niparko: From Analyst to VP of Product

   1. KNKevin Niparko0:00

      I think the key learning is go listen to your smartest customers. Sit next to them. Really learn what they are doing with your product, because that can really inform and give you early signal as to what's gonna be big. (instrumental music plays)

   2. HSHarry Stebbings0:11

      Kevin, I am so excited for this. As I said, it's so unfair. I hear so many stories about you before, uh, but I'm so ready for this. So thank you so much for joining me first.

   3. KNKevin Niparko0:21

      Absolutely. Thanks for having me on.

   4. HSHarry Stebbings0:23

      Not at all. But I wanna start with your beginning, because you started as an analyst. So how did you make the move from analyst to product? Let's start there.

   5. KNKevin Niparko0:33

      Yeah, yeah, yeah. Absolutely. So, you know, happy to be on, and really ex- excited to share some of the stories around building Segment over the years. Uh, yeah, so I actually started as Segment's first data analyst, so I was really helping their early team figure out the business model, product direction, and go-to-market strategy through our own internal data. I joined right around the Segment Series A, and, you know, being the lone data analyst at a very small data company means you're often the internal customer who's using the product every day, sort of the frontline tester for a lot of the new ideas, the dog eating the dog food. And so, you know, I developed this perspective on how the product should work, specifically geared towards analysts, uh, business intelligent use cases. And so, uh, I had really formulated a, a perspective on the opportunities that were sitting around the data that Segment was helping our customers collect. And as Peter and the CEO and, uh, fo- co-founders were formulating the product, he made the hop over to, uh, product from a- analytics.

   6. HSHarry Stebbings1:36

      Can I ask, did you find it an easy transition to make?

   7. KNKevin Niparko1:39

      Yeah, yeah. It's a great question. I like to think analysts make incredible, uh, product managers, largely because, uh, you're forced to think broadly about the business, really dive deep into data, both quantitative and qualitative, and the signals that you can gather to really inform strategy. And so, you know, I felt like there was a great foundation there. I also think being, uh, you know, in the early stages of a company, you end up playing a lot of different roles, uh, and seeing a lot of different parts of the business. So analytics took on the role of growth at times, of partnerships, of sales ops, and so you really get a unique lens across the business sitting in analytics.

   8. HSHarry Stebbings2:18

      I think it's so important to have that multifaceted view so you can have the empathy for each part of the organization. But before we dive into kind of products

2. 2:26 – 5:00

   Biggest Takeaway from Bridgewater

   1. HSHarry Stebbings2:26

      and a lot of the products, you were also at Bridgewater, which does shape so many people's perspectives in many ways. Calvin told me I had to ask this one. What are one to two of your biggest takeaways from your time at Bridgewater?

   2. KNKevin Niparko2:37

      Yeah, yeah, yeah. Uh, Bridgewater is definitely a pretty special place. Uh, I don't know how many of the listeners know what Bridgewater is, one of the largest asset managers in the world. Uh, also committed to building an organization that's all about radical transparency and honesty and ruthless pursuit of the truth. So Ray Dalio is the founder, has written a lot about, uh, his management principles, and those are very much embedded in the organization and the culture there. I think there were really sort of two interesting learnings here. The first is around, uh, really trying to better understand how people think around you to sharpen your decision-making. Especially in business conversations, uh, you know, in the workplace, people are often talking about and debating opinions, right? So like, "Harry believes option A is the best option. I believe option B, and we're going to debate option A versus option B to figure out which one is superior." But I actually think there's something more valuable, and the approach that is often taken at Bridgewater is really trying to understand how Harry got to option A, right? What is the data that Harry is seeing? What is the mental model that Harry has of the world that is leading to that perspective? It's through understanding that way of thinking and processing that you can actually refine and sharpen your own decisions by really understanding those around you and debating and openly understanding how people are approaching their decisions. And, you know, I think the second big takeaway is actually pretty similar, which is how they approach, uh, their trading systems, which is highly systematic. And so Bridgewater is essentially some of the smartest people in the world encoding their market understanding in this giant prediction machine, and constantly refining that machine as, uh, new information is gathered, as feedback is collected from the markets. And so most organizations, most teams are dealing with the things that are coming at them, and not systemizing and building the machine, uh, that can help them solve future problems. And so that approach around, you know, being highly systematic and systemization in everything that you do can really help accelerate the team over the long run.

   3. HSHarry Stebbings4:52

      If we think about... Oh, sorry, I'm jumping around, but fuck it, I love this discussion. If we think about like speed, efficiency, systematization, when we're doing

3. 5:00 – 8:37

   The Tradeoff Between Speed of Execution & Listening to Feedback

   1. HSHarry Stebbings5:00

      product discussions, there's a... Gustav, the CP at Spotify said on the show, "Talk is cheap and so we should do more of it." I always find that a hard one because I think discussion actually can slow everyone down, debate isn't always needed, let's just go. How do you balance in your head in product between hearing everyone's feedback and input without losing velocity and speed?

   2. KNKevin Niparko5:24

      You know, I think there are probably two parts to that. The first is this trade-off between speed and quality, and I think people typically believe that this is a trade-off and, uh, you need to make a decision where you wanna fall on the spectrum. I think one of the things that we've learned at Segment is that the faster that sh- you ship, the faster you learn all of the ways in which you are wrong, and all of the ways in which you can make it right. Reality and customers and procurement teams are very unforgiving, and the faster that you get your ideas out into the market, the faster you're gonna learn. And so, of course, you have to ship responsibly. Uh, of course, you can't go around breaking things that are really important for your customers, but moving quickly is, uh, I think really a key to unlocking that next level of quality.

   3. HSHarry Stebbings6:12

      I, I think the other thing is also like very rarely does something take a long time, but it was perfect because it took that longer time. Do you know what I mean? It's like, actually, you learnt more when you just shipped it, so I totally agree with you there. I, I always also oscillate when I think about like... Actually, fuck it. I do have to ask one more thing before we dive in, but it's like Segment was an amazing journey, yeah, ended with an incredible obviously to Twilio where you are now. What are one or two of your biggest takeaways from the Segment journey that've really impacted how you think about product?

   4. KNKevin Niparko6:43

      You know, I think a really important part of the Segment story was that the founders, you know, before anybody joined the company, had really struggled to find product market fit for a few years before landing on Segment.

   5. HSHarry Stebbings6:57

      Yeah.

   6. KNKevin Niparko6:57

      And so, there was a really high bar internally for being rigorous thinking around what it takes to achieve product market fit. You know, I had the privilege of being able to introduce Segment's second product, and, uh, this was really introducing sort of the first customer data platform on the market. We'd spent the first six months really sort of shaping the idea, researching this with customers, iterating on their feedback, but we were running into a ton of technical problems. Uh, we, w- customers weren't really ripping this thing out of our hands, and Tito, who, you know, was essentially our, uh, product and engineering leader, the grownup in the room for a lot of Segment's story, uh, sat us down and he, he essentially told us we had three months to make the project work or the project was dead. And so, it was the exact deadline that we needed, pressure that we needed. We ended up cutting a ton of the bells and whistles and things that we thought we needed and really simplified down to the product that customers were looking for. You know, I think there are a few takeaways from that. The first is you need to be rigorous and honest with yourself and your team when things are working, when they're not, and why they're not, but then I think the more important piece is that constraints can really breed creativity, right? By shortening the runway, you can actually move faster and get to the right product faster. And so, uh, really thinking about compressing that timeline and driving towards, uh, that creative approach when you have constrained resources.

   7. HSHarry Stebbings8:30

      It's so funny you say about the creative approach and then you say about kind of compressed timelines and the kind of process there. It makes me

4. 8:37 – 10:56

   Product: Art of Science?

   1. HSHarry Stebbings8:37

      think of this kind of challenging debate or balance for me in product, which I never know the answer to, which is product art or is it science? You know, a- again, Gustav at Spotify, he was contrarian. He said that it's 99% science and we overestimate how much art there is. Um, others... Uh, he's the only one that says that, by the way. (laughs)

   2. KNKevin Niparko8:58

      (laughs)

   3. HSHarry Stebbings8:58

      Uh, so my question-

   4. KNKevin Niparko8:59

      It's-

   5. HSHarry Stebbings8:59

      ... to you is, is it more art or science?

   6. KNKevin Niparko9:01

      It's a really fun question to wrestle with. You know, I think about product management is all about building great products that users love that are aligned with the long-term interests of the business. And so, if you break that down, right, you have building great products, which I think boils down to great discovery and really understanding customer needs. And there, I do think that there is a highly scientific approach that you can take, uh, and repeated process that you can build around that. Uh, then there is building things that users love, right, taking those prob- p- problems and actually translating that down into creative solutions given the technology landscape, uh, where the market is at. I think that is going to largely boil down to an art, uh, which sits somewhere between, you know, design, engineering, and product management disciplines. And then, uh, there's, of course, making sure that where you are heading is in the long-term direction of the business, and that requires deep market understanding, understanding where competitors are at and where they're likely to move and what their long-term strategy is relative to yours. And so, there, I don't think you can boil that down into a formula. So I'd say mostly art.

   7. HSHarry Stebbings10:12

      Kev, Kev, Kevin, put a number on it. What's art, what's science?

   8. KNKevin Niparko10:16

      (laughs) Uh, 80% art, 20% science.

   9. HSHarry Stebbings10:21

      Ooh, I like it. No, I, I totally agree. I always think it's actually a little bit like a jazz band which is like, you know, you can listen to a saxophonist on their own and it's nice, just like you can pick up a product if you really look for it and it's good, but you need the growth, you need the marketing, you need the trumpet, the horn, whatever it is to come together for it to be a really successful entity.

   10. KNKevin Niparko10:43

       It's a great analogy.

   11. HSHarry Stebbings10:45

       Thank you. I'm a podcaster for a living, so-

   12. KNKevin Niparko10:47

       (laughs)

   13. HSHarry Stebbings10:48

       ... I'm, you know, pretty, pretty much this is my job. I remember, I'm in the arena, Kevin, okay? Um-

   14. KNKevin Niparko10:53

       That's right.

   15. HSHarry Stebbings10:55

       ... (laughs) uh, you said before that there's

5. 10:56 – 15:00

   The 4 States of Product Teams

   1. HSHarry Stebbings10:56

      four states to product teams. I love this framing because I really find the structure quite helpful. What are the four states and how should founders think about this?

   2. KNKevin Niparko11:05

      Th- so it's a pretty powerful model for thinking about the performance of your product teams and...... how you can get them to the next level. So, if you just imagine this grid where you have shipping, fast and slow, and you have impact, high and low, as the other, uh, you can really think about mapping where your product teams are relative to those two dimensions. And so, over time there are really only four states that a product team could be in. You can have a team that's not shipping, and there are a lot of reasons that can go into that. Uh, maybe they introduced a feature that led to an outage, and so there's a lot of fear on the team. Uh, maybe they got a lot of feedback from a last product ship, and so, uh, they're reticent to move the needle. Maybe they don't have a clear strategy, and so they're in tweaking mode. And so, essentially, they're not delivering, uh, on the roadmap. But you really need to, uh, to unlock this state you really need to think about, uh, how can, how can you get them into shipping mode? Have them ship something really small, and then celebrate the heck out of it to really encourage that feedback loop to get into the mode of delivering for customers. The second state you can have a team that ships, but they don't... they aren't delivering impact. And so, here the pace of development is good, they're moving really quickly, but it's relatively low-impact work.

   3. HSHarry Stebbings12:29

      How do you measure impact? Sorry. Is it like alignment to corn or star? How do you as a product leader measure impact?

   4. KNKevin Niparko12:36

      It's a great question. You know, I think, at the end of the day you need to be looking at customer outcomes, or whatever those outcomes are for your product area. I think about, uh, for Segment and customer data infrastructure, we really think about unlocking use cases around customer data. So, what are the ways in which we are actually influencing end user and customer journeys to improve the product experience for our customers through data? And so, you know, really thinking about what is the end value that you are delivering for your customers, and are you continuously achieving that?

   5. HSHarry Stebbings13:13

      I totally get that. Okay, so in there we're shipping fast with low impact. Not great. Um, what's next?

   6. KNKevin Niparko13:21

      So, finally there's the good stuff, which is you're consistently shipping and you're consistently delivering high-impact work, and teams in this state are generally going to be really high-context, they're gonna be high-trust across engineering, design, and product. They're very h- high-talent density, right? So you have a lot of great people that are working there, and they're empowered to take risks. This is the bar that you want to set for your entire EPD org. When you have a team in this state, you wanna figure out ways in which you can keep it intact and keep it going, and really get the heck out of their way. But by looking at product teams through this lens you can really think about what are the different strategies that you need to take to get them to continuously deliver, and continuously deliver high impact?

   7. HSHarry Stebbings14:04

      If we're a founder listening to this, if this is the four states of product teams, I feel totally unequipped for this as a generalist founder. When should I hire a CPO to be on top of this?

   8. KNKevin Niparko14:15

      Great question. At Segment we had a bunch of, uh, really technical founders, right? So, uh, we had four very talented, very product-focused, and very technical founders. Uh, we also brought in product-focused engineering leaders early on. We never really had a CPO in the traditional sense. Uh, Tito, who I mentioned earlier, probably played the closest role to this, but also managed engineering and security and design over the years. And so, I think the biggest consideration is, where is your founding team at? What are the biggest gaps, uh, that you need to fill? And really thinking about a CPO as, uh, somebody who can play the role of up-leveling the product organization, but needs to be complementary to the founding team.

   9. HSHarry Stebbings14:58

      What's the hardest thing about bringing in

6. 15:00 – 21:45

   Tips for Hiring Product People

   1. HSHarry Stebbings15:00

      a CPO, do you think?

   2. KNKevin Niparko15:01

      Yeah, I think there are really two hiring mistakes when it comes to hiring product people. The first is not really having a clear understanding of the role that you're hiring for, right? So, there are a bunch of different archetypes that you can hire. Some product people really spike in strategy, some really excel in culture-building and team-building and people management. Others specialize in go-to-market partnership or product execution, right? And so you really need to be crystal clear on what you are looking to hire for. And then the other, I think, is really being deliberate and committed to hiring for those set of spikes. You know, I think allowing a committee to dictate a hiring decision is never good. At the end of the day, the hiring manager, the CEO in this case, needs to be empowered to make the decision even if there isn't consensus among the hiring team.

   3. HSHarry Stebbings15:56

      Uh, sorry, I'm writing down, uh, because, uh, do you have to touch on the hiring process there with that? First off, how do you stage hiring for new product hires? We have a first meeting, what do you want to achieve in that first meeting? Is it a get-to-know-you? Is it a case study? What does that first meeting look like if we're running a process?

   4. KNKevin Niparko16:14

      Yeah, absolutely. You know, the hiring process really starts well before the first meeting. There's a lot of internal discussion, debate, and wrestling that goes into defining the role and the spec that w- we're looking to hire for. And I think that is upfront work that will really pay dividends as you move through the process as a hiring manager. You know, i- i- a good example of this, we're hiring right now, we're backfilling a director on my team, uh, who just left to go do his own startup. A lot of our conversations internally are, uh, what are the sets of qualities both in terms of leadership, product leadership, but also the things that this person had brought to the team that we are looking to, uh, you know, persist or, uh, continue on? And so, this person was a sales engineer, had great relationships with our go-to-market team, uh, was a technical expert internally on the product. And so, while we're looking for a great product director, we're also looking for those sets of qualities that, um-... are maybe less directly tied to the role and more complementary to the entire team. That's really how we think about designing that role and spec that we are looking for, and then the challenge is going out and finding and testing for those spikes.

   5. HSHarry Stebbings17:27

      Let's say we have three candidates that we're looking at. How do we structure that process? If you were to advise me as, like, an early-stage founder, how would you advise me on how to structure that hiring process for product people?

   6. KNKevin Niparko17:39

      So that first call that we're gonna have, you know, it's gonna be talking about career or product experience, sort of a get-to-know-you. Uh, and then we think about structuring the interviews in a few different buckets. First is around product strategy, which is talking about sort of big bets and decisions that this person has, uh, led within an organization. You have execution, which is how do you take that large strategy, translate it down into an executable roadmap, and then actually deliver on it? You have people management for, uh, s- you know, CPOs and product leaders, and then technical fluency, which is, you know, we do run a relatively technical product, and we're selling to engineers. And so, we do expect our product team to have a certain level of technical fluency.

   7. HSHarry Stebbings18:28

      When you look at those different buckets, where would you say is the most common aspect that, that they fall down on amongst those buckets?

   8. KNKevin Niparko18:35

      Product strategy is probably the most, uh, difficult for candidates, uh, as they work through sort of their impact. I think it's really important to think about, "What is the overall direction of the business? Where is go-to-market at? Uh, how do you think about bringing together all of the needs of the business, balancing those into a cohesive strategy, and then being able to articulate that strategy and incept that into your organization?" And so, that's generally the hardest area to hire for, and I think it's one of the most amorphous to test for.

   9. HSHarry Stebbings19:13

      Do you give case studies?

   10. KNKevin Niparko19:15

       Our strategy interview, uh, takes a few different forms. Without giving too mu- too many details away here, we cover, uh, both internal, uh, decisions that we are currently wrestling with, so sort of a live conversation, and talk through how the candidate would approach, as well as talk about the candidate's experience. But we don't give theoretical cases or, uh, external cases throughout the hiring process.

   11. HSHarry Stebbings19:40

       You mentioned that committees maybe aren't the best way to hire. That's contrarian. Most people say an interview panel is quite useful. Why is a panel or a committee not a useful way to conclude a hiring process?

   12. KNKevin Niparko19:52

       I think there's, is definitely value in getting a bunch of different diverse perspectives from your team, ula- quality of a candidate, and working through these different dimensions of a candidate's experience. Uh, but at the same time, at the end of the day, uh, a hiring manager is the ultimate decision-maker. I view the hiring team as really an input into the decision, which ultimately needs to be owned with the hiring manager. At the end of the day, that's the person who's going to be working most closely with this person and who's gonna be responsible for their long-term success within the organization. And so, therefore, they should be empowered to be the decision-maker.

   13. HSHarry Stebbings20:33

       I totally agree with you there. Carlos, when you review your hiring mistakes, my biggest is I've overweighted brand. I've seen that they've come from a big logo, and I've gone, "They must be brilliant." And they're not, uh, very often. Uh, what are your biggest hiring mistakes when you reflect on hiring for product teams?

   14. KNKevin Niparko20:50

       It's a great question. I think overweighting, uh, skills and, uh, specific domain expertise is a common one that I've fallen into specifically with hiring product people. Uh, you know, the best, uh, product leaders within our organization are generalists, can, uh, apply their craft to a bunch of different domains. There are very few cases where we needed specific knowledge and skills, uh, to bring onto the team that was really the key input into a decision. More often than not, uh, that is going to be, uh, something that y- somebody can learn on the job. And so, you know, you don't wanna overweight skills. Uh, instead, really focusing on experience, the overall craft of product management, and making sure that they're at the bar there.

   15. HSHarry Stebbings21:41

       It's interesting you said there about kind of s- the specific skills. When I speak to

7. 21:45 – 23:50

   Product Leader: Specialization vs Flexibility

   1. HSHarry Stebbings21:45

      many of, uh, our mutual friends, they, they described you as a man of many talents, meaning that you are an all-arounder. You do lots of things well. How important do you think it is for product leaders to do a little bit of everything versus be much more specialist and work on the machine rather than in it?

   2. KNKevin Niparko22:03

      Wow, great question. You know, I think it's tough to be a product leader in a product-led organization, because you're responsible for so many different things, right? If the product doesn't sell, uh, right, you're the one who's on the hook. Uh, if your team is flooded with support requests, uh, generally, product needs to go figure out what is wrong with the product. If you're misaligned on margins or the product doesn't scale, yes, that's a systems and engineering problem. But also, at the end of the day, you're trying to meet your customers' needs. And so, I think the beauty and the challenge of being a product leader in a product-led organization is that you're uniquely positioned to solve these issues, uh, even if they're not traditionally product problems. But I think what that really begs is, you know, somebody who can go out and learn really quickly a bunch of different disciplines and then, uh, you know, go solve the hardest problem within an organization regardless of whether it fits into a product bucket or an engineering bucket or a go-to-market bucket. I think a great example of this was, uh, when we introduced, uh, Personas, which was a new product offering, an add-on to our core product within Segment, we really needed to spend the next year as the product team who was closest to the discovery and the customer needs going out, pairing with our sales team, and really delivering it to market. Essentially spent a year in sales, uh, and then, uh, you know, another six months in professional services and implementation, uh, ensuring that our customers were getting the most value out of our second product. And, you know, I think this is, uh, just a great example of, you know, our product teams will really figure out what needs to be solved and go do it.

   3. HSHarry Stebbings23:45

      You said there about kind of like, uh, really immersing yourself in sales. A big part of sales

8. 23:50 – 29:28

   Tips for Product Demos

   1. HSHarry Stebbings23:50

      still stays demos, showing the value of the product ahead of time. I heard you were incredibly talented when it comes to creating demos at speed. Can you walk me through your- This... Calvin was like, "Get him to walk you through his process."... for creating demos. Would that be possible?

   2. KNKevin Niparko24:07

      Yeah, absolutely. (laughs) So, uh, you know, one of the challenges with building product is you ha- have to believe in this future state that's better than today. That can be really hard for people, because they don't necessarily feel it. They're familiar with the status quo. Change is really hard. Like, uh, do you remember this example of, of Bill Gates going on Letterman and explaining why Letterman needed the internet?

   3. HSHarry Stebbings24:34

      Yeah, I do love that.

   4. KNKevin Niparko24:34

      I think it was, like, in '95. And, like, Letterman's just, like, completely confused by why anybody would need to listen to a baseball game on the internet when there's radio. You know, I think you run into these types of pushback, both internally and externally, when building new product. And I think demos can be a huge unlock here, which is, how do you pull that future forward and really deliver that experience? Like, how can I make Harry really feel how much better his life will be with the product that we're about to build, or the idea that we're looking to pursue? You know, I think it really ties back to your pr- your customer problems, the things that you wanna solve, and really being able to showcase that the thing that you are building towards is going to solve an acute high priority problem for your customers. I love weekly demos with my team. I think that's probably the way in which we can most shorten the feedback loop. There's not a ton of overhead or polish that's required. It's really about, you know, pull up the terminal, show me what we've built over the past week, and, uh, what are the, what is the end-to-end value that we are creating. And so demos can be this great vehicle for that.

   5. HSHarry Stebbings25:47

      If you were to leave a meeting with your team sad or angry post the demo, what are the reasons that you leave sad or angry?

   6. KNKevin Niparko25:56

      Demos are incredibly energizing. Never leave sad or angry. But I would say th- there's a key unlock here, which is, uh, you need to commit to your demo a week ahead of time. Right? So you need to say, "What are you going to deliver next week?" And then you work backwards from that. The times in which we've had demos that didn't go well, it's generally because we hadn't really set the bar for what we were going to deliver the next week. You know, it's amazing how much, uh, of the demo or the product gets built in the five hours before demos. Right? That deadline is a really helpful forcing function for being able to go from wherever you're at, to a way of showcasing and explaining what you've built.

   7. HSHarry Stebbings26:45

      When do you do the demos?

   8. KNKevin Niparko26:47

      Thursday or Friday. And w-

   9. HSHarry Stebbings26:49

      Thursday... Morning, mor- morning or afternoon?

   10. KNKevin Niparko26:51

       It fluctuates based on teams and calendars, but, uh, generally in the afternoon.

   11. HSHarry Stebbings26:56

       Do you have any rewards or negatives for good and bad? I'm just thinking of incentive structures and accountability. What can be done to increase quality of demos?

   12. KNKevin Niparko27:06

       Delivering a great demo is fulfilling in and of itself, right? So you show your demo, people clap, people are excited, people are asking questions. And so I do think that the reward is innate in the process itself. I also think you then get to, you know, then ex- re- reuse this demo to go explain to the go-to-market team, go ex- show this to customers. You know, I think at the end of the day, uh, great product teams are, uh, really excited about delivering value for customers. And being able to showcase their demo and get that feedback, I think is a great way of learning and seeing that feedback in action.

   13. HSHarry Stebbings27:43

       For me as an early stage founder that you're advising, what are the mistakes that you suggest I avoid when it comes to demos?

   14. KNKevin Niparko27:51

       There are sort of two pitfalls here. The first is that they become too high stakes, right? And so people feel like they need to put a lot of polish and prep-

   15. HSHarry Stebbings28:01

       Mm-hmm.

   16. KNKevin Niparko28:01

       ... into their demo. And so they spend a good chunk of their week on overhead and polish, as opposed to the actual core components of the demo. And so that's why encouraging, you know, people to show docs that they've written, pull up the command line, uh, and really show off whatever that is, uh, that they've been working on, in an end-to-end, uh, full value delivery, I think is really important. And then the other that I would say is, uh, you know, not making it too performative. It doesn't need to be, uh, a ton of people, a huge group. It can be down to your product pod, or a small team that's been working together.

   17. HSHarry Stebbings28:43

       Does the way that you... I'm really drilling in deep here. Does the way that you do demos change when product teams are remote versus in person?

   18. KNKevin Niparko28:51

       Yeah. We've definitely had to adjust through the pandemic, uh, and now as a fully remote, remote organization, think about how we can structure this, uh, differently, better. Uh, we do have this concept of asynchronous demos as well. So, uh, to the extent that people are working in different time zones, aren't able to make, uh, demos, can submit a recorded version of their demo, which, you know, is just as good. We'll watch it, uh, and everybody will, you know, give their feedback there.

   19. HSHarry Stebbings29:22

       You mentioned that kind of, uh, A, kind of the asynchronous element there, but also maybe sharing stuff that you've written as

9. 29:28 – 33:36

   The Importance of Good Writing

   1. HSHarry Stebbings29:28

      well. I heard what a brilliant writer you were.

   2. KNKevin Niparko29:30

      Mm-hmm.

   3. HSHarry Stebbings29:30

      And you said before about the importance of product people learning to write. Why do you think it is so important that product people are able to write, and how do you advise them to learn?

   4. KNKevin Niparko29:40

      You know, there's this great interview with, uh, one of the writers of The Onion. Do you know The Onion? It's a satirical newspaper.

   5. HSHarry Stebbings29:48

      Ah. I know the publication. Yeah. Yeah.

   6. KNKevin Niparko29:51

      Yeah. Yeah. (laughs) One of the premier publications. But there's this interview with the writers, and they go through their, their, their process in the writer's room for coming up with headlines, and then the articles that they end up writing for The Onion. It's interesting, 'cause they come up with like hundreds of headlines every week.... and they eventually whittle that list down to, I think it's, like, 10 to 15 articles that actually get written. And the difference between all of the ideas that get generated in the room and what actually gets written is that there's no real substance to the joke that they come up with in the writer's room, right? So they give this example of, uh, a woman crying at the penguin museum-

   7. HSHarry Stebbings30:32

      (laughs)

   8. KNKevin Niparko30:33

      ... and it's, like, it's ki- it's kind of, like, funny on the surface, but then you sort of ask yourself, like, "Wh- why is that funny?" There, there's no, like, there's no meat to that joke, right? And I think ideas have this i- illusory nature, which is, on the surface they seem really good, but when you force yourself to sit down and write the idea down and really unpack it, either they don't seem as good as they do on the surface or, by comparison to all of the other ideas that are out there, this one is not the highest ROI thing that you can be working on. And so I see writing as really this forcing function for thinking, for testing these ideas, and really understanding if that oasis on the horizon is actually filled with water or if it's just a mirage.

   9. HSHarry Stebbings31:23

      Okay. So let's just t- I, I totally agree with you. I find the same with, actually, investment memos. When you actually write about a competitive landscape, it really crystallizes, oh, shit, this is really fucking competitive, versus just thinking about it. So I totally agree with that. But if we think about writing with regards to product and prioritization crystallizing thinking, what does that mean that we do? I'm a product manager listening. Should I write product reviews? Like, w- what can I do? Help me understand. I should write what now?

   10. KNKevin Niparko31:54

       So, you know, I think a lot of the great product thinking gets encoded into this concept of a PRD or a product requirements document. Uh, these can take multiple forms, but I really think, at the end of the day, the thing that you are trying to articulate is what is the customer need? What, what have you learned through the discovery process? What are the key problems that you are looking to solve? And why is your team, your organization, your product uniquely positioned to solve those problems? It's not about solutions. It's not about, uh, how you can solve them. But it's more about what and why you are solving that problem. And so this concept of the PRD is really powerful. It creates structure for product teams to really be able to articulate and synthesize everything that they've learned from going out and talking to customers and encoding that into a packet, a document that everybody can engage with, read, give feedback on, and iterate on.

   11. HSHarry Stebbings32:53

       How do you create a habit in writing? How do you c- like demos, where you said weekly, enforcing that time constraint, how do you create accountability incentive structure to writing behavior?

   12. KNKevin Niparko33:05

       Yeah, absolutely. That's where product reviews come in, which is really a forum to discuss, uh, product requirement documents and really go through them. You know, being able to have a forum where, uh, product leads can discuss their learnings, share their learnings across the organization really creates that incentive and that forum to, uh, be able to get product teams to sit down and write and synthesize and work backwards from the product review conversation that they want to have.

10. 33:36 – 36:45

    Product Reviews

    1. KNKevin Niparko33:36

    2. HSHarry Stebbings33:36

       Okay. Product reviews, everyone does them very differently. How often do you do a product review?

    3. KNKevin Niparko33:41

       We've gone through a bunch of different iterations on product review over the years. At times, it's been sort of wildly centralized and seen as sort of a gate to projects before they get green lit. I think my view has evolved quite a bit here, which is product review is really an opportunity for PMs to gather additional input and drive additional alignment across the organization. And so we run product reviews on demand as product teams are at a point where they want additional input. Flexible list of attendees who can attend. Uh, generally we'll include some folks from go to market, product leadership, uh, anybody who, uh, design and engineering, anybody who can really weigh in and help sharpen the thinking there. I think it's really about empowering product teams to, uh, really own their own destiny.

    4. HSHarry Stebbings34:29

       Can I ask, how do you drive outcomes from these product reviews? I find a lot is, like, discursive debate. How do you drive meaningful outcomes for product leaders and product teams to have tangible takeaways? What should they do?

    5. KNKevin Niparko34:43

       I think a key component of the PRD and the product review really comes down to a set of clear decisions that you're looking for the team to weigh in on. There'll be, you know, large questions that need to be answered and really being able to pull that out of the folks that are coming to product review through a set of very targeted questions here.

    6. HSHarry Stebbings35:06

       Do you send them ahead of time? Do you let the people that you're sitting down with prep, or do you throw it on them in the meeting with the PRD?

    7. KNKevin Niparko35:14

       You know, pre-reads generally sent out 24 hours in advance. If, you know, you're working up to the last minute of a product review, which happens from time to time, you'll create 10 to 15 minutes where everybody can sit down, read it, and think, uh, and comment in the doc. Really wanna create the space for, you know, not only for product teams to write PRDs but also for folks who can really help sharpen the thinking to read it and weigh in on it, and so need to create the space and time to do that.

    8. HSHarry Stebbings35:44

       Kevin, how do people fuck up product reviews?

    9. KNKevin Niparko35:46

       I would say there are two general mistakes that teams will make. The first is going to be jumping too quickly to solutions, right? So they have a great idea, uh, and they're sort of working backwards from the solution. That's one, and then the other is, tying back to our conversation around demos, not giving a clear feeling and experience that you're looking to deliver at the end of the day for the customer. What does it look like to actually solve this problem for a customer? Why is that experience going to be unique to our position?... uh, and what we are building. And so I think those are probably the two biggest pitfalls.

    10. HSHarry Stebbings36:32

        Speaking of, uh, (laughs) interesting lessons from, from anything, I, I think one that I have from this prep session that I did was around your take on memes. And Calvin also told me to ask this. He said,

11. 36:45 – 43:41

    Product Memes vs Product Road Maps

    1. HSHarry Stebbings36:45

       uh, that you said before about product memes are more important than your roadmap, and you said that before to me. What did you mean when you said product memes are more important than your roadmap?

    2. KNKevin Niparko36:57

       (laughs) Yeah. So, you know, uh, with all the talk about how important it is to write as a product leader, I think at the end of the day most people are never going to read your PRD. Most people are not actually going to review your, you know, 20-page roadmap, no matter how well-written or thought through it is. And so product memes are this concept of really simplifying your thinking down into the shortest, simplest, most memorable perception of your product, and then distributing those ideas through the meme. All right? And so th- if you think about memes, they're generally these distillations of really complex ideas and, uh, structures. It's about compression. It's about taking these different ideas and creating knowledge shortcuts for people. And so I think a good example of this is, like, memes gone wrong, right? The ways in which, uh, memes can work against you. If you think about a sales team that has lost faith in the quality of the product that they're selling, that in and of itself is a meme. It spreads, uh, at the water cooler, uh, over drinks at the end of the week, and it not only hurts your sales but it also becomes self-fulfilling and it spreads. This is sort of the dark side of the meme, and you can, you can invert that and think about ways in which you can control the narrative and really build alignment around what you are building through exciting memes. I think, you know, we had a few cracks at this at Segment over the years, so these can be big ideas and campaigns.

    3. HSHarry Stebbings38:30

       What makes a good product meme versus a bad product meme?

    4. KNKevin Niparko38:33

       So I think simplicity is one. Uh, really accessibility for folks, and then memorability, so the fact that it is actually something that you will remember, you will walk away from that conversation remembering. So I think a few examples of this, you know, we had a big campaign, uh, for Segment which was called, you know, What Good Is Bad Data? And it's just sort of a catchy phrase which helps you understand data quality, at the end of the day, is going to be really important for, uh, your data strategy. And I think they can also be really small. So we had, uh, this feature which was essentially self-healing identity graphs, obviously complex, very deep in the weeds, but we called the project Project Roomba, uh, after the beloved self-driving vacuum cleaner. And, you know, that sticks with people. It, it allows them to understand what you're doing even if they don't understand the specific details of it.

    5. HSHarry Stebbings39:28

       I think humor, one, and I also think, uh, real time is really important. When there is a news cycle, make it funny. I find real time current affairs integration is one of the most important things for resonance.

    6. KNKevin Niparko39:41

       Absolutely.

    7. HSHarry Stebbings39:42

       Yeah, I totally get you. Has your mind changed around, like, the seriousness of product? I know it sounds stupid, but, like, when you enter and you're young in your career, it's a lot more academic, I think, a discipline, than one approaches it with today, where you have, you know, an importance of product memes as quite central.

    8. KNKevin Niparko40:02

       Yeah, absolutely. And I think this gets back to the conversation on art versus science, right? When you start your career in product, there is a lot of learning and skills and craft that you can pick up by following the playbook, and then I think the reality is, as you grow, uh, within product, science is, you know, a helpful start, but at the end of the day it comes down to creative thinking and ways in which you can solve problems across the organization. And that doesn't always boil down into a template or, uh, a specific process. It can often be these really creative, funny ways of getting people to understand the work that you're doing.

    9. HSHarry Stebbings40:43

       Dude, I, I, uh, speaking of, like, across the organization, I feel so sorry for you from a resource allocation perspective, because you have to, like, weigh up product that generates revenue today. You then have to also weigh up innovation, staying ahead of the game, how to introduce AI and every other, you know, exciting new technology into the existing product suite, and then just scaling and growth. How do you balance between core product innovation and scaling as a product leader?

    10. KNKevin Niparko41:09

        I think those are the three buckets. Having that, uh, framework around the three horizons I think is really helpful. What are you doing well today, what is emerging over the course of the next one to two years, and what do you need to do long term, three to five years out, uh, that's gonna set your product and org up for success? You know, I do think that the allocation across those buckets are going to swing. Especially in the early days, that Segment would swing pretty wildly between, you know, 90/10/0, really honing our, the quality of our core product in the early days, to really periods of innovation where we're trying to expand, build new products, and really solve new problems for our customers, when it looked probably more like 30/40/30 across those different buckets. But I do think that being aligned with your founding team, uh, with your leadership team around where you wanna fall across those investment areas is really key to ensuring that you're making the right decisions and allocating resources the right way.

    11. HSHarry Stebbings42:13

        Have you ever got that allocation wrong?

    12. KNKevin Niparko42:15

        One of the early challenges around, uh, w-... building segment was around scaling our integration catalog, right? So we have, you know, hundreds of different tools and APIs that we connect to, and there, I think, you know, quality is really important, which is, uh, customers expect a really high-quality integration with a new tool. These APIs are constantly changing, and, uh, they're, you know, emerging r- today on the MarTech landscape, I think there are like 10,000, 12,000 different marketing and analytics products that you can connect to. And so it becomes a really big challenge of, uh, building a cohesive and really high-quality catalog for our customers. And so I think there were periods where, you know, we weren't investing, uh, the right, uh, focus in integration quality, and I think that ended up showing up in some really hard conversations that we had with customers, and realizing that we had probably been too focused on expansion and new products and not investing sufficient capacity in really ensuring our, uh, core product was high-quality for our customers. You know, we've come a really long way from those early days, and you have to make some really hard calls as a product leader when you're growing so quickly.

    13. HSHarry Stebbings43:39

        Two questions for you. One,

12. 43:41 – 48:20

    Introducing Your 2nd Product

    1. HSHarry Stebbings43:41

       I'm an early-stage investment of yours. How do you advise me, a CPO or a product leader, on when's the right time to do product two?

    2. KNKevin Niparko43:50

       We, I think, waited a really long time at Segment to introduce our second product, which I think was a function of our core product was, uh, growing really quickly, and we felt like we had a lot of runway. I think the key piece to keep in mind is, what does that growth rate look like one to two years out? And, uh, I think that's probably the right time. When you see that flattening, uh, or starting to stall out, you know, one to two years out in the future, you really need to be ahead of that. I really encourage folks to stay focused on core product as long as possible, but also knowing that you need to be thinking about the long term, and new products and second products take, uh, a while to build, hone, and deliver to market. And so you really probably need, you know, 12 to 24 months to make that a reality.

    3. HSHarry Stebbings44:42

       No, I totally agree with you. Sometimes you release a second product, it doesn't hit. How do you advise product leaders on when to give it more time, it just needs a bit more time, it needs a bit of tweaking, versus, "You know what, Kevin? We got it wrong. We need to pull it." How do you balance between the two, and how do you advise me?

    4. KNKevin Niparko45:00

       It's hard because there's a lot of sunk-cost fallacy, right? We spent a lot of time building this. We have a lot of- a large investment here. But I think the reality is if customers aren't ripping the product out of your hands, that is your signal, you know, really ensuring that you have thought creatively about ways in which you can deliver this product to market, have really tried all and exhausted all of those ideas. But when you hit product-market fit, you will definitely know, uh, you know, been, uh, fortunate enough to experience that multiple times at Segment, have also been on the other side where customers are not pulling this product out of our hands, and I think you need to look at those hard situations and make the call that it's probably not the right thing to be investing in if you are not able to really break through.

    5. HSHarry Stebbings45:50

       I do have to ask, speaking of kind of, you know, when it works and the product-market fit being very obvious there, and then also pulling product, if you think about two reviews, and then we'll do a quick fire. But is one your best product decision? What was it, and what did you learn?

    6. KNKevin Niparko46:04

       You know, one of the first, uh, products that I worked on at Segment was around, uh, data warehousing and what we called Segment Warehouses at the time, and this was helping our customers get direct query access to their customer data in their data warehouse. I think back in 2015, this was very early. Warehouses have played this key role across Segment, uh, has really been a huge growth lever for the business over the years, and I think the reality or sort of how we got there was we went out and we listened to some of the most advanced customers that were building things around Segment and had actually built some, you know, very hacky workarounds to load data into a data warehouse from an S3 bucket, uh, and they helped us realize what the potential could be for data warehouses. And so, you know, I think the key learning there is go listen to your smartest customers, sit next to them, really learn what they are doing with your product, because that can really inform and give you early signal as to what's gonna be big.

    7. HSHarry Stebbings47:05

       Flip side, everyone makes mistakes. What was the biggest product mistake, and how did you learn from that?

    8. KNKevin Niparko47:11

       You know, I think there are a few cases where we built instead of partnering, and I think there is a lot of opportunity, more opportunity than product teams typically see, to actually start with a partnership and, uh, really expand your product capabilities through what others are building. You know, I think on the surface, a lot of these products seemed really simple, but when you clicked a few levels deeper, there were a lot of dragons hiding beneath the surface, and it was a lot harder of a challenge than we had initially given it credit for. And so, you know, I think I would just advise founders and product people, don't fall into the build trap. Really put a, a premium on partnerships and go explore those, especially when you're thinking about areas that aren't necessarily your core competency.

    9. HSHarry Stebbings48:01

       I love that. Um, I always think about like Shopify and Stripe as a great example, which is obviously Shopify could build a Stripe internal, but actually, it's not core, and they should focus on where their business is. So I totally agree with you.

    10. KNKevin Niparko48:14

        Great example.

    11. HSHarry Stebbings48:16

        Um, I... (laughs) Again, podcaster. My job is to come up with witty statements.

13. 48:20 – 50:34

    Quick-Fire Round

    1. HSHarry Stebbings48:20

       Uh, I'd love to finish on a quick fire, Kevin. So I say a short statement, and you give me your immediate thoughts. Does that sound okay?

    2. KNKevin Niparko48:25

       Let's do it.

    3. HSHarry Stebbings48:26

       So, tell me, when do you listen to users and when do you ignore them?

    4. KNKevin Niparko48:30

       I'd say always listen to their problems, but rarely listen to their solutions unless they've built something that is a working solution and are willing to show you it.

    5. HSHarry Stebbings48:40

       How does AI impact the future of product?

    6. KNKevin Niparko48:43

       My sense is that we'll see a rise of a product architect role which combines the disciplines of product and design and engineering into one, and uses AI as leverage and an accelerant to really deliver new products to market.

    7. HSHarry Stebbings48:57

       Wha- one piece of advice would you give to a product leader starting in your role today?

    8. KNKevin Niparko49:02

       Uh, I would say go on a listening tour, right? So when you're early, you can ask the most fundamental questions about your customers and the product that they're using, and I think that's the best place to start.

    9. HSHarry Stebbings49:14

       I'm a really early PM in my early PM career days. What advice would you give to me on what I can do to get promoted?

    10. KNKevin Niparko49:21

        Go solve, uh, real, urgent problems for your customers.

    11. HSHarry Stebbings49:25

        Tell me, what in the product toolkit could you not live without?

    12. KNKevin Niparko49:29

        I would say Gong for sales intelligence.

    13. HSHarry Stebbings49:32

        How do you use Gong?

    14. KNKevin Niparko49:33

        Uh, two use cases. One is searching for keywords-

    15. HSHarry Stebbings49:37

        Yeah.

    16. KNKevin Niparko49:37

        ... specifically around roadmap, uh, and specific topics that we're looking to dive into, and then the other is for more quantitative research, how frequently are certain terms or products or features coming up in sales cycles.

    17. HSHarry Stebbings49:52

        Yep, agreed. That's interesting. I, uh, I like that use case. Final one for you. What recent company product strategy have you been most impressed by?

    18. KNKevin Niparko50:00

        Yeah, I would say Retool moving from internal tools to a low-code app builder.

    19. HSHarry Stebbings50:08

        Mm-hmm.

    20. KNKevin Niparko50:08

        I think this is going to be a incredible opportunity for product builders to be able to build with less technical tools, but be able to deliver on data-informed apps.

    21. HSHarry Stebbings50:21

        Listen, my friend. I love doing this. I know we've jumped around, but I cannot thank you enough for maybe putting, uh, such a cohesive schedule together and it being so comprehensive. So thank you so much for being such a great guest.

    22. KNKevin Niparko50:33

        Really appreciate it, Harry.

Episode duration: 50:34