The Exchanges

Q Okay. First question. What are two or three books that you've recommended most to other people?

A The dream machine, uh, which is a tremendous history of, uh, prehistory really of modern computing, uh, ostensibly following the life of JCR Licklider, but really much broader than that is a tremendous missing piece of history. In my opinion, I think in my discipline in computer science, we were not properly educated We learned about Alan Turing and we learned about some of the technical underpinnings of computer science theory, but the modern computer and the path to it is a profound and fascinating one. And it has particular resonance today as JCR Licklider's observation was human in the loop computing. And I think we are now in human in the loop AI. And I think there's a tremendous, uh, resonance there. The second one is, is good inside, which is Dr. Becky's book. And I, again, I think it's a tremendous parenting book. But more than that, it does contain lessons for how we think about our own emotions and how we manage those, which I find to be useful in any context.

AI assessment note: “The dream machine... The second one is, is good inside”

Q On the topic of bottom-up, I imagine you're a big fan of this book that everyone always talks about, The Body Keeps Score, I think it's called. Would you recommend that book? Is it connected in a large part to the stuff you talk about? What do you think of that, that book specifically? Because I hear about it all the time.

A Yeah, it's a good book. Um, it's by Basil van der Kolk, and there's another, I think Peter Levine says, the issues are in the tissues, is basically, is basically the concept. And this is the idea that we have these Incomplete mobilization reflexes that are stored in our body and often held as tension. It's not strictly true to say that the trauma is in the body. There's actually a cortical map in the brain, which kind of tracks these things, but for, for kind of practical purposes, it looks and feels as if there is stored grief in my right hip or anger in my solar plexus. Like that's, that's the experience that we have. And the more that you Become aware of these sensations and start to, yeah, develop emotional fluidity essentially. The more that, that tension is released and the less reactive you become and the more emotional debt you pay off. So I think the body keeps the score. I, I think a more accurate way would be the body is the scorecard in a way. I think that's kind of a slight reframe. Um, and if you're interested in this, the work of Peter Levine Waking the Tiger is kind of the seminal book on, on this, like, mobilization reflex stuff that I'm, I'm describing.

AI assessment note: “Yeah, it's a good book.”

Q read somewhere that you've interviewed over 2500 people over the course of your career. And so kind of going back to the beginning of a career, or at least getting a job, what have you found is most helpful in standing out as a candidate when you're interviewing and just essentially getting hired? What advice do you have for people that may be going through an interview process right now?

A There's a lot of evidence that suggests that, um, the number one and two factors in any interview are appearance and enthusiasm. And it doesn't mean you have to be beautiful, but, you know, show up somewhere looking like you're interested in the job, not in your pajamas. And most importantly, be enthusiastic. People want to work with people that want to work with them. So if you seem very judgmental of the company and like, you have to sell me on it. You're going to turn them off. I look at every interview of whether or not I really want this job. I might've decided I don't want the job. I still want the offer. And so I come to any interview I do leaned in and talking about how excited I am to be a part of this opportunity and what I know about the company. Beyond those cosmetics, the biggest thing I see particularly higher levels Is people talk about what they have done, but not why it mattered. They don't talk about the impact. See, a leader is not hiring someone to just do work. They're hiring someone because they have a problem or a need. And so if you can show them, look, here's the things I've done that have made a difference. Here's the things I've done that have helped. My past employers where I've had an impact. So I didn't just do work. That makes you a worker. Someone who has an impact is more of a leader and leader doesn't need to mean people manager, just a higher …

AI assessment note: “number one and two factors in any interview are appearance and enthusiasm.”

Q Never one's ever mentioned Top Chef before, so that's fun. Do you have a favorite interview question that you like to ask candidates that you're interviewing for a job?

A A lot of my interviews now are trying to help people decide if they actually want to join a company. And so my, my favorite, my favorite company question I ask now is like, Hey, We've really loved you. You're going to come through. I think you're going to get a lot of offers from other companies too. I bet you'll have three or four really compelling offers because you're a fantastic candidate. How are you going to figure out really specifically which of those options are right for you? And I think it forces people to tell you what they want. And then you tell them why you have that more than anyone else. And then you can actually like pitch them on what matters versus pitching on things that don't.

AI assessment note: “my favorite company question I ask now is like, Hey, We've really loved you”

Q What are two or three books that you've recommended most to other people?

A I really love Elad Gill's High Growth Handbook. It's organized into chapters about sort of foundational company building, building a leadership team, building a board. And in addition to the thoughtful synthesis on that topic from Elad, there's also, he has a, like an interview of someone that he does relevant to that, that section on each of the chapters. Really, really great read and, and super actionable if you're a leader in a, in a, a young company. I mean, in a completely different end of the spectrum, I, I love big, complicated science fiction. Um, and, uh, I mean, there's like a lot of garbage science fiction out there to be sure, but when you find something special, it's like, it's the best. So probably through the years in that category, there's a book called Hyperion by Dan Simmons. That's, it's just like a total classic. Everybody should read it.

AI assessment note: “I really love Elad Gill's High Growth Handbook.”

Q I can't wait. You talked about this. Lower spend, lower expense life. What other tips and tricks do you have for people to create this space where they can continue living and, you know, paying the rent while exploring and wandering and exploring these things? Is it cut down on expenses? Is there anything else that one can do?

A I've talked to so many people at this point. I've seen all sorts of things. I've seen people move abroad. I've seen families with kids and a mortgage sell their house and decide to live in a RV. I've seen people, uh, dip into their retirement. I've seen people ask, apply for grants and get those. I've seen people apply for loans. A big move that a lot of people do is turn their current job into a contract job, which a lot of employers are a lot more open than people would think. Because a contractor is very easy to fire. You can fire a contractor in a day. So if the company is struggling, boom, you're gone, right? And so there is more risk, but if you're sort of known in the company, it can actually be a somewhat stable path to create more space in your life. You say, hey, I want to work three days a week. I want to be a contractor. Here's exactly what I want to do. Are you open to this? And as soon as you're a contractor, they can't tell you where to work.

AI assessment note: “A big move that a lot of people do is turn their current job into”

Q just launched where you can kind of train your own GPT and that'll be fun. And actually a podcast listener reached out to me and offered to help build this thing. So that's a huge success story from this podcast. Next question. Two more questions. Do you have a favorite life motto that you find yourself coming back to, sharing with friends, finding really useful in work or in life?

A One coming alive over getting ahead. That's something I keep coming back to. I'm default skeptical of chasing achievement. And I use this to remind myself that it is about that personal energy versus extrinsic outcomes. I'm very convinced from my own life experience that the extrinsic outcomes aren't going to do a ton for me. Sure, I need to make enough money, but when I'm in extended states of like feeling alive and connected to everything I'm doing in my life, that is, that's it. Like, and I basically repeated this mantra to myself right before rejecting the book deal. It was like, I did not feel good in the conversation with the people. They talked down to me. They told me that like, I probably wouldn't succeed. And it was like coming alive or getting ahead. I don't need their prestige.

AI assessment note: “One coming alive over getting ahead. That's something I keep coming back to.”

Q do it well. Let's actually get into what the role actually is. I think it's a really confusing role. A lot of people hear product ops and that they don't know what, what it is. There's like maybe research synthesis, there's some data stuff. What's the simplest way to think about what is the general consistent roles of a product ops person and what they can do for your company?

A The way we think about it is, is kind of structured around the three pillars that we talk about in the book. So business and data insights, more of the quantitative side, making sure that the product manager has, you know, all of these sort of engagement and revenue inputs to make smart decisions, the, uh, customer market insights. So the qualitative, then we talked about this a little bit earlier in terms of like finding folks to speak to, making sure you're speaking more to more than one just customer. And, uh, finally the third pillar is, is process and practices. So it's really around those areas and it depends on what your company needs and where the biggest opportunities and challenges might be.

AI assessment note: “structured around the three pillars that we talk about in the book”

Q Maggie, what are two or three books that you've recommended most to other people?

A First, most common one is probably the presentation secrets of Steve Jobs. It's a little tiny one. Really great way to improve your speaking skills and your presentation skills and to get, ah, distracted executives to agree with the point you're making. So that's one. Thinking in Bets by Annie Duke is the second one. I'm coming back to the point about being able to make bets. I think that one's a really interesting one. And then bonus third one. This is more like a desk reference that I now have on my desk. The Scaling People book by Claire Hughes Johnson. I really enjoyed the way that one is working and it just sits on my desk and I reference it every once in a while, especially as a manager.

AI assessment note: “First, most common one is probably the presentation secrets of Steve Jobs.”

Q What are two or three books that you've recommended most to other people?

A The one book I recommend because I truly, it really changed the way I think about things. It taught me a lot about a discipline I had never really thought much about, but also because I think it makes me sound smart, and it's a really short book, so it's easy to get through, is the design of everyday things. For me, that was the first time that I realized that design wasn't just this sort of, like, cool thing that some people were into, and they had to get, and it made things beautiful. It was about understanding how everything is designed, and How to think about design and usability. So for someone like me who didn't have any experience in product before, I think it could be transformative. And then the second book, it has nothing to do with what we do. I recommend Viktor Frankl's man's search for meaning because at heart I'm a philosopher and I tend to think a lot about life, the meaning of life and you know, what, what differentiates one life from, from the next and, and how to, how to live a good one. And no matter what profession we choose, that continues to be important. So those are my recommendations.

AI assessment note: “is the design of everyday things... Viktor Frankl's man's search for meaning”

Q So you're Chief Product Officer at Wyze, which I don't know if you knew this, but I'm a very happy, uh, weekly active user of. To give folks a little bit of context on Wyze, could you just explain what does Wyze do and also share maybe a few stats to give people a sense of the scale that Wyze has reached at this point?

A We're looking to solve the problems associated with cross-border money movement. Which is that moving money across borders is pretty slow. It's actually really expensive, and it can be really hard to do. We solve it with three products. Our money transfer product, which is what we started with. Our account, which we like to think of, uh, trying to solve the problems of international banking with our account for people and for businesses. And then finally, we've also got an enterprise product. Where we take the underlying infrastructure that's powered those products that we built and embed them in the banks and products that people use every day, and then zooming into the numbers. So we've got to come up a little way on the journey. So today we're now moving about twelve billion dollars a month, growing at between 30 to 40% year on year. We take about .65% on average across all our routes as price. And we've been profitable for about more than four years now with 20% EBITDA margins, but probably that's that I'm most proud of. And the hardest thing to make happen out of all of that was, uh, we acquired 70% of the users that found out about Wise last month through word of mouth. So, contextually, we have sixteen million customers, and we're acquiring about a million a quarter, um, about ten million actives, and, um, yes, and a million that joined Wise the first time, 700,000 found…

AI assessment note: “We solve it with three products... So today we're now moving about twelve billion dollars”

Q I just watched that too. So good. You can actually stream it now. I don't know when this comes out, but it just, uh, yeah, you can watch it on home. Uh, but it's not cheap. I think it's like 20 bucks in the US. What is a favorite interview question you like to ask candidates when you're interviewing them?

A Yeah, it's only asked to, I got down to asking just two questions over time. The first one's probably my favorite, uh, which is, what is it that most frustrates you about, like, instead of why you're leaving, what frustrates you the most about where you're working right now? And this is as, uh, people, people always tell you why they want to join Waze or join whatever company you're coming to, and that's not that interesting, but what's interesting trying to figure out is what they're running away from. And usually there's something broken there that's really wound them up. But what's more interesting is they've been unable to fix it. And so in asking this question and probing, you kind of get quite good at getting a sense of like, what is the limit? What's the thing they found and what did they get stuck with? And you kind of say, okay, you're gonna run into that here every day, every week, or you should be fine. And that's, uh, that's kind of why I asked that question.

AI assessment note: “what frustrates you the most about where you're working right now?”

Q I'm more excited that you're here. So you're head of growth at Deal. For people that aren't familiar with Deal, can you just give us a sense of what does Deal do briefly? And then also, can you share some stats around the trajectory of Deal? It feels like it's been this extraordinary journey, and I'm curious just to hear some of the stats of just how, how extraordinary.

A Yes. So Deal is payroll, HR, and compliance platform for global teams. So essentially we help companies expand globally with tools like DealHR, immigration, employer of record hiring, independent contractor hiring, payroll, both global and US. So whether you're trying to hire someone as a full-time employee in Japan, or you're trying to make sure your contractor in Germany has everything they need on day one, our platform allows you to do, take care of everything all in one place. And when I joined the deal, actually that was around July, 2020, we were less than a million dollars in ARR. And then over time, it grew within the first year on January, 20, 21, we were at four million dollars ARR. We finished 20, 21 with fifty seven million. April, 22, 22, we were looking at a hundred million. And then we started off this year with two hundred and ninety five million dollars in ARR. And we're, what we're particularly proud of is that we've been even a positive. So that's something that we are very, very proud of on top of the ARR growth.

AI assessment note: “So Deal is payroll, HR, and compliance platform for global teams.”

Q Okay. So what you didn't mention is some of the most, uh, interesting stats about RAMP and the business and the growth kind of story of RAMP. So could you just also share some stats about just the, the success of RAMP and a sense of just like how rare the, the story of RAMP has been?

A Yeah. I mean, we were one of the fastest growing fintech and, and maybe SAS companies of all time. I think we've hit a hundred million in annual for first two years. And we've continued to grow significantly since then. I think every day about a thousand users join, join our platform. And, you know, this year we've grown to hit six hundred million in savings, uh, and 8.5 million an hour saved for our customers by, by controlling spend and automating a lot of the manual tasks. So, uh, we're continuing to grow fast and, uh, and, uh, in terms of just raw transaction volume, you know, we have crossed ten billion in analyze spending on the platform and just getting started.

AI assessment note: “we've hit a hundred million in annual for first two years”

Q Um, with 50 people, which is incredible, and so just kind of on that point, how do you do so much with so few PMs especially? Do you have anything that you figured out that ends up being really important there?

A I think that by eliminating or reducing the size of the team, we've forced other people in the company to think like PMs. And I think it's been a huge value add to our culture. You know, when I say product that people will think about like product management, but I actually think product is anyone that actually reports into, into our CTO and to, and that's product engineering, product design, product managers. Product data scientists. So making everyone feel like a PM is a great way to get leverage as a PM. And, and that means basically empowering the designer to think about the actual specs and priorities and scopes more than you or empower the engineer to take something that's. Fairly lightweight in terms of a spec or direction and actually thinking, think through it deeply and come back with some, some great questions that the PM hasn't thought through. So that's one thing. The, the, the, the second is that we, we invested early on in product operations, which was a team that, that also reports to me that basically focuses on the operational functions of, of product. That's everything around. Um, whether it's project management or, or issue management or release management or enablement and, and, and content, uh, beta and customer research, they basically are tasked with a lot of the, the work that that needs to get done to, to continue shipping products and scaling product …

AI assessment note: “making everyone feel like a PM is a great way to get leverage”

Q not all, maybe half are like, I still don't think we have product market fit. Like they're at like a billion dollars valuation, growing like crazy. And like, I feel like I have product market fit with the current users, but I don't with the people I want. And that's what you're describing, right? It's like the new, you stopped having product market fit with people that you wanted next.

A I think that's exactly right. I think of like product market fit is almost like you keep stacking these S curves where you get product market fit in a small group, and then you suddenly reach like exponential growth because you can crack that whole group, that type of audience. But then you start declining because you start hitting the ceiling of like, we've gotten, I don't know what it might be, every development team in the US to be using this product. And then you jump up to the next S curve, which is like, how do we get technology savvy teams that aren't developers? Or how do we get People who are, you know, in large enterprises who are outside the U S and these each kind of be, these each become the new curves that you have to build product market fit for. And I think it's just all a huge exercise in like being self-critical, being humble, not, not presuming that you've cracked this thing forever and keeping kind of a very beginner's mindset of what does the next audience need that your previous audience didn't need at all.

AI assessment note: “I think that's exactly right. I think of like product market fit is almost like you keep stacking”

Q That reminds me of a story you told me about how you made your eng team do some manual work of an algorithm involved in transformation. Can you share that?

A Okay, so I'm gonna preface this story by sharing that I'm a huge math nerd, and one of my favorite books on logic is called Gödel Escher-Bach. And in this book, there's a fun scene where there's an ant farm that bands together to do the work of a computer flipping bits from zero to one to solve logic gates. And so this chapter of that book was really the inspiration for an exercise that I ran my team through. So about a year ago, We were doing a big zero to one new project at dbt Labs, and we were going to change the algorithm for how we built customers' data transformation graphs. And I needed a way for the team to really internalize all of the changes that we were going to make, and I needed them to own it because otherwise they wouldn't be able to anticipate all of the edge cases. It wouldn't be quite as durable. You couldn't copy paste the algorithm. So I showed up to a team offsite with a spool of rope and, uh, sticky notes. And I think my team looked at me crazy, went with two heads when I started to tie people up to create a graph. So each node of the graph was an engineer, and I, ah, the rope was kind of the edges of the graph to connect them. And then we worked through the new algorithm extremely slowly, step by step. And it was a way that you couldn't leave that exercise without knowing exactly what was going on, because everyone had a role to play. So I think a lot o…

AI assessment note: “I showed up to a team offsite with a spool of rope and, uh, sticky notes.”

Q couple more things just to make them super concrete for folks that might be listening. What's an example of an area? Like what's an actual team that would be an area? And then the other question I have just while I'm saying questions is, Are there some metrics you could share, just like what some of these teams might be gold on, just examples of how you think about metrics?

A The area that came to mind when you asked about one of our areas is something called coordinate, and their, their job is effectively making sure that the slice of Asana that helps teams work together is working effectively. And so that's projects and tasks and the data that you might put into tasks and All of the back and forth that is required when people use Asana for their core working team. Some of the metrics that they care about are like org paying weekly active users, as well as really thinking about like healthy project use. So we make sure that we understand like what does good look like and what is, what is a dynamic that we want to be creating in terms of people getting real value from using the product. And we build that into our metrics to have as a guardrail To ensure that we're not driving one metric at the expense of people really getting what they need out of Asana.

AI assessment note: “The area that came to mind... is something called coordinate... metrics that they care about”

Q Spotify for over 14 years, which is a rare feat in the tech world, and you've held a lot of different roles while you've been at Spotify. Can you just start off by giving us a sense of what these various roles and what you've done over the years at Spotify, and then just what are you, what are you up to these days? What are you responsible for now?

A So I came into Spotify in Early, 2009, late, late, 2008. And my job then I had been an entrepreneur, started some of my own companies in the back then very, very early sort of feature phone, smartphone space. So I had a bunch of knowledge there. I had sold the company to, to Yahoo in the mobile space. I worked there for a while. I came back to Sweden and then I met through a mutual friend, Daniel Ekta, the CEO and co-founder of Spotify. And they had built the desktop product already, the free streaming desktop product, and it was amazing and I could try it, but they needed someone to figure out what to do with mobile. And because I had been an entrepreneur in that space, I got that job. So my job was to, to head up mobile for Spotify and figure out what the mobile offering would be, which was a challenge because obviously Spotify desktop was a free on-demand streaming application. And back then specifically with edge networks, You couldn't really stream at all in real time. The performance wasn't there. And also you could, you couldn't fund that with an ads model. So it was a product and business model innovation that was a lot of fun. So that's how I started. Then after a few years, I took on all of product development for Spotify. And then a few years later, I actually took on the technology responsibility, sort of the CTO role for Spotify as well. And recently my official ti…

AI assessment note: “recently my official title is co-president of Spotify... I run the product and technology side”

Q but just like there's Slack and then Slack kind of, I don't know if it's true, but it feels like Microsoft Teams is eating their lunch with bundling. And I'm curious, what do you think of bundling as a strategy to win long term? And also how do you compete against say a Microsoft that maybe one day bundle your product for free and you might be in big trouble?

A I think it's two separate questions, so let me take them separately. The first is, what do I think about bundling? So small and medium-sized companies will go from being a single product company to a multi-product company in order to progress, because you need a diversified financial model, because you need to be able to sell new products into your customer base who should already be friendly to you if they like your products. Um, and because you need to really expand your total addressable market to get to be a billion dollar or two billion dollar company. So I, I believe in bundling as a growth strategy. Specifically for product-led growth companies, bundling is not a great land strategy. So at Atlassian, we had a number of products and experimented with different bundled lands, and it really slowed down the product-led growth motion. So we ended up going back to land with a single product. High velocity, single person uses it quickly, starts to get value, and then come in with, with, with other things. So from that perspective, product-led growth, bundling is not very effective. Bundling for a sales-led motion is pretty effective when you're at the right stage of growth. And then as far as the question of competing against Microsoft, you know, there's these two parts of the philosophies, a best of breed and an all-in-one. And Oracle was an all-in-one and Microsoft is an all-…

AI assessment note: “I think it's two separate questions, so let me take them separately.”

Q Great. What are some products that you've recently discovered or use regularly? SAS products or even consumer fun random products that you want to share?

A Yeah, I, I can't go through this podcast without giving a shout out to Notejoy. So Notejoy is a fast and focused notes app for individuals and teams. And so that's the company that I work on. So I use it for everything from, you know, our product roadmaps to my coaching notes, to even prepping for something like this podcast. You know, I use Notejoy all the time. Another one that I really use a lot is Captio. It's been around for a while, but it's a little iOS app. I don't know if it's on Android, but basically it's a blank notepad. You can dump your brain into it and there's one button and it emails it to you. And so when I find that I'm really distracted or I just want to remember something, I use Captio all the time just to quickly capture my ideas and then I process it later in my inbox. And then something that I just downloaded this week is Arc, the new browser, and I'm actually really excited about its vision. I'm not sure if I'm going to work it into my workflow yet or how it fits in, but it's, it's really beautiful and it's really cool to see someone iterating on the cluster that is browser tabs.

AI assessment note: “Another one that I really use a lot is Captio.”

Q I'm honored as well, so thanks for joining me again. I have a lot of stuff that I want to chat about, but first of all, I'm just curious, what are you up to these days? I know you left Eventbrite as CPO. I know you're doing a few advisorships with startups, but how are you spending your days, and what do you think is next for, for Casey Winters?

A So I'm still, still spending some time with whatnot and Eventbrite as, as advisors. You know, I stepped back from the, the CPO of Eventbrite in October, but still working on some Long-term marketplace strategy stuff, some growth strategy stuff. Uh, I'm on the board of a company called Beek, which is like Netflix for audio in Latin America. And I'm doing some angel investing and in marketplaces and what I call tech debt as a service, which is, you know, what are startups that are building out things that were hard for my teams in the past to like build or maintain inside previous companies. The other thing I'm working on is revamping the product strategy program. For Reforge. So I got some things keeping me busy, but, but definitely not as busy as I was last year.

AI assessment note: “I'm still, still spending some time with whatnot and Eventbrite as, as advisors.”

Q Gojek. Many people listening have never heard of Gojek, especially people in the US. So just to start, can you just like describe what is Gojek? What do you all do? And then also I think more interestingly is just like the scale of Gojek. I think people in the US, their mind will blow once they hear The scale you've reached with this company, they probably hadn't heard it.

A So Gojek started as a motorcycle taxi based service. So it's a kind of a uniquely Indonesian thing where we have millions of motorcycle taxi drivers in all of the urban centers in Indonesia. And so we started with a very local problem. And the first product was a on demand super app, if you will, where you could ask Someone on a motorcycle to give you a ride, send a package for you, or buy something and deliver it to you. This then evolved over the years into, you know, a more general on-demand consumer super app that also included, you know, car drivers and other services ranging from the ones mentioned to grocery deliveries and payments and financial services. And today, we took the company public about a year and a half ago after we merged Uh, with, uh, with Indonesia's top e-commerce platform. And, uh, we've managed to also expand outside of just Indonesia, where today we have about, uh, 2.7 million drivers across Southeast Asia. Uh, we've completed about three billion orders, uh, last year. So that's three billion orders. So that the scale of our region is, is often, um, under underappreciated. Um, where we also have about fifteen million merchants, um, doing, you know, general e-commerce, but also, you know, restaurants and our food delivery service, um, and on that IPO, um, you know, we were pretty proud to say that, you know, it was Indonesia's largest, uh, IPO of all t…

AI assessment note: “we have about, uh, 2.7 million drivers across Southeast Asia. Uh, we've completed about three billion orders”

Q things comms and PR. I've never met a founder or product leader who doesn't want to get better at spreading ideas and getting their product out there. And you're very good at this. We're going to talk about some of the things you've done in the space, but just to start, maybe just broadly, I'm curious to hear just like, what have you learned about what helps an idea spread?

A So there's a few ways to make the idea spread. The overall principle is you have to make it memorable and you have to make people want to say it of their own volition. And so what doesn't make them want to say it is doing a favor for a corporation. What does that make them want to say it is they want to bring joy to somebody else. They want to make somebody laugh. They want to appear interesting, or they want to project some part of their identity. And so A few things that you can do with an idea to make it spread better. You can make it into a joke. So you can turn it into a line that people will repeat. Uh, you can use an analogy. You can take something and just say it over and over. Move fast and break things. Don't be evil. Build something people want. You can create a mental image that is very colorful. So I have a mental image for people that I use a lot, which is put the pill in some cheese. And we can talk about it later. It's about how to craft a story that will, that will stick. But when I say put the pill in cheese, people tend to remember that and it's more easily repeatable. And then the last thing is use a story, use an anecdote instead of using adjectives, because adjectives are so subjective. They're meaningless to people. So if you give them a story, that's something they can repeat over the dinner table.

AI assessment note: “The overall principle is you have to make it memorable and you have to make”

Q Speaking of templates, I know Airtable kind of known for templates being, and you mentioned this being a big part of the success. And I imagine a lot of companies now are just creating templates left and right, because they imagine that's the core, what helped a lot of these companies notion being an example. What is your take on the power and importance of templates for software?

A I think they can be tremendously helpful if you are horizontal because they help to narrow the surface area for a user so they understand how to connect the dots between like their problem and your product. And if it is not obvious to someone how they can solve a specific problem, they're gonna like be like, oh, hey, that seems really cool. When I think of something, I'll definitely come back and then you have lost them. And so if you can be like, here are three templates that a person like you might be excited about. That can be really helpful. Where people sometimes get confused about templates or have the wrong expectations about templates is when they think that templates are going to be an acquisition mechanism and they don't build in the foundation that is necessary for that to be true. So a lot of people think that templates were what drove like Airtable's top of Sunnel. That is not the case. I, I was having a conversation with someone who works a lot on SEO at Airtable in the much later days. And, and sort of laughing over the fact that people thought that was a big source of traffic because it was not. We did not optimize them for that. Good luck finding them in search most of the time, like not at all useful. Where they were helpful, you know, narrowing that surface area, helping with sort of matching patterns, helping people understand how the product worked, super h…

AI assessment note: “I think they can be tremendously helpful if you are horizontal because”

Q process now, you can claim a special discount exclusively for Lenny's podcast listeners. 15% off the first four weeks of working with your new software developer. Grow faster with an extra pair of hands. Visit lemon.io slash Lenny. I know you have some insights on prioritization and some strong opinions on how to prioritize. Can you talk a bit about that and how you advise your product teams to prioritize?

A One really common framework in prioritization is RICE, reach, impact, confidence, effort. And I think it's simple and fairly robust, which is, I think, generally good qualities of a framework. But one of the traps with RICE that we observed is that the C and E, the confidence and effort, Tends to cause you to prematurely deprioritize potentially high-reach, high-impact bets, really innovative things. And we encountered this on one of our teams early last year where we just riced everything, all the ideas, and a lot of the high-reach, high-impact things ended up at the bottom because confidence and effort were just so murky for them, as they should be typically for, for high-reach, high-impact ideas. And so one exercise that we push our teams on is just ignore the C and E for a little longer than it's comfortable.

AI assessment note: “one exercise that we push our teams on is just ignore the C and E”

Q Friggin love Andor, huge plus one on that. Favorite interview question that you like to ask?

A My favorite interview question is tell me about a product that you love. And I can have that question last five minutes. I can have that question last 60 minutes. And so that's the first question that I'll typically ask people during a screening interview. I use the word love very deliberately. I want to see what products in their lives they really gravitate to and they engage with and that they can use that word with. That helps me understand a lot about what they, what they value. And then I'll ask a whole series of questions, which is, you know, Why do you love it? Why do you think other people love it? You know, what would you like to see about it in the future? Pick a feature that you'd like to build for that product. Why do you think that's a good feature? How would you measure the success of that feature? So I've used this for years. It's just such a good way to help understand the product sense that a person has helped get to know a person a little bit better. It's always interesting when people pick products that are more physical products to see what they're into, um, in terms of hobbies and things of that sort.

AI assessment note: “My favorite interview question is tell me about a product that you love.”

Q One thing, uh, you mentioned is Evernote. I don't know how much you can talk about this, but they just got sold, right? Someone bought Evernote. And if I think back to Evernote, it feels like they could have been Notion, which is killing it right now. Any, any thoughts on what maybe they missed and didn't turn into Notion along the way?

A Yeah. Uh, we're gonna clear some cobwebs here. Um, it's been a while, but one challenge that Evernote really struggled with was this evolution from single player to multiplayer, to team, to enterprise. It's a chasm that a lot of bottom-up SaaS businesses struggle to cross. Evernote was philosophically antisocial. You know, it was meant to be your second brain, kind of your personal tool. And I think that capped the company's growth potential. You know, I always used to say, you can't retrofit collaboration. You have to be collaboration first. And a lot of companies now really take that for granted, but back in mid 2000, this was going to be a new way of building product. And so we missed that bridge. If companies do that well, it benefits every metric. That bridge from single player to multiplayer, you know, acquisition goes up. You grow organically through referrals and shared workflows. Retention goes up because now you have these Shared workflows that are incredibly sticky. You know, employees are accountable to each other to say, this is how work gets done. Like design in Figma, you know, roadmap planning and ticketing in like JIRA or linear. It just becomes the default platform. And monetization goes up, right? You know, revenue scales with usage. And so the more people using it, the more they use it, you start tripping the wire on paying more and more over time. And so Ev…

AI assessment note: “Evernote really struggled with was this evolution from single player to multiplayer”

Q Let's just start with a quick overview of your background. Could you share some of the wonderful places you worked, some of the wonderful projects you worked on, and then just a bit about what you're working on today?

A Yeah, happy to. Um, so some quick background. Grew up in Haiti, studied computer science in college, went to business school. My first career was actually not in tech. It was in medical devices. I was a GM for a company based out of France and also overseeing West Africa business for them. After doing that, I moved back to the U.S., launched my own startup, which didn't work out. And then I moved to the Bay Area roughly eight years ago. And in the Bay Area, I wanted to become a PM, which was really hard to get into. So at first, I joined a startup, Series A company, became head of product for them, and then joined Slack as the first PM on their growth team. And then from there, helped scale the growth team at Slack. When I joined, revenue was around fifty million. When I left roughly four years ago, it was 10 extra. And then after Slack, I recently joined YouTube Google about two years ago. And at Google, I'm a product lead at YouTube. Where I, I'm driving a product called Primetime Channels, which actually recently launched in November in the US. And in that product, we're bringing streaming services to YouTube so that users can watch their favorite movies, shows, and sports content.

AI assessment note: “I'm a product lead at YouTube. Where I, I'm driving a product called Primetime Channels”

Q Absolutely. My pleasure. You have such a fascinating background working at so many world-class companies with so many fascinating people. Could you just take a minute to talk about some of the wonderful things you've done in your career, just to set a little context for folks?

A Yeah. Um, well, thank you for characterizing them as wonderful. I feel like it's been a quite circuitous path. Um, but definitely has taken me to some interesting places. I started off as a journalist at the Wall Street Journal and then found my way into communications and marketing at Tesla Motors, where part of my responsibility there was to sit to Elon's right and make sure he had all the data he needed at his fingertips when talking to the press, which was, you know, deep end of the pool on the PR. Learning. And then after that, found my way to First Round Capital, where I was really fortunate to be at the ground floor of First Round Review, if anyone out there watching this is familiar with those pieces. Was there for about five years. Loved that team. Really incredible folks. And then they had invested in Notion really early on, and so I was able to meet Ivan Zhao as a result of that, and him and Simon, and they gave me the opportunity to join as the first marketing hire at Notion. And that's what I was doing up until recently.

AI assessment note: “I started off as a journalist at the Wall Street Journal and then found my way”