Building high-performing teams | Melissa Tan (Webflow, Dropbox, Canva)

Melissa Tan is an advisor, investor, and growth expert. She’s worked with fast-growing startups like Dropbox, Canva, Grammarly, and Miro, and for the past 2.5 years has been the Head of Growth at Webflow. There, she led the company's self-service business across Product, Marketing, and Growth, in addition to leading the charge on pricing and packaging. Prior to Webflow, she was Head of Growth for Dropbox’s B2B product, where she played a pivotal role in propelling their growth. In today’s episode, we discuss: • Attributes of high-performing teams • Tips for developing talent and seeking a mentor • How to create a strong culture of ownership • Frameworks for hiring PM and growth talent • Common pitfalls companies face when implementing growth strategies • Lessons from scaling Dropbox • The DACI framework for increasing team velocity • How to actually embrace first-principles thinking — Brought to you by AssemblyAI—Production-ready AI models to transcribe and understand speech | Mixpanel—Product analytics that everyone can trust, use, and afford | Eppo—Run reliable, impactful experiments Find the transcript at: https://www.lennysnewsletter.com/p/building-high-performing-teams-melissa Where to find Melissa Tan: • Twitter: https://twitter.com/melissamtan • LinkedIn: https://www.linkedin.com/in/melissamtan/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Melissa’s background (04:12) What’s next for Melissa (06:45) Lessons learned from Dropbox (11:49) When to add sales to product-led products and vice versa (14:28) Managing people with a people-focused and results-oriented approach (17:14) An example of people-focused leadership (20:26) The importance of talent development and why Melissa invests in it (22:26) Tips for finding a mentor (24:58) Specific questions to ask when you are interviewing for a role (27:49) Companies Melissa has worked with (28:33) Attributes of high-performing teams (31:38) Creating a sense of ownership among team members (34:36) Building a team-first culture (36:54) Avoiding burnout by knowing your limits (39:24) Developing talent and unlocking potential within your organization (42:45) Melissa’s hiring practices and what she looks for in a product manager (44:40) The exact interview sequence Melissa utilizes (49:58) Common pitfalls when creating growth teams (53:43) “Flying formation” and the DACI framework (56:48) Who should own revenue (58:19) When to invest in growth (1:01:06) What to look for in your first growth hire (1:04:35) When it’s appropriate to hire an advisor (1:06:19) First-principles thinking (1:09:50) Lightning round Referenced: • Jiaona Zhang on LinkedIn: https://www.linkedin.com/in/jiaona/ • Lean In: Women, Work, and the Will to Lead: https://www.amazon.com/Lean-Women-Work-Will-Lead/dp/0385349947 • Tim Ferriss: How to Find a Great Mentor: https://www.youtube.com/watch?v=RVo1aZCyfO4 • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375/ • How to Monetize a Freemium Business: https://www.ycombinator.com/blog/how-to-monetize-a-freemium-business • DACI framework: https://www.productplan.com/glossary/daci/ • Leaders Eat Last: Why Some Teams Pull Together and Others Don't: https://www.amazon.com/Leaders-Eat-Last-Together-Others/dp/1591848016/r • The Untethered Soul: The Journey Beyond Yourself: https://www.amazon.com/Untethered-Soul-Journey-Beyond-Yourself/dp/1572245379/ • The Four Agreements: https://www.amazon.com/Four-Agreements-Practical-Personal-Freedom/dp/1878424319 • Winning Time: The Rise of the Lakers Dynasty on HBO: https://www.hbo.com/winning-time-the-rise-of-the-lakers-dynasty • ChatGPT: https://chat.openai.com/ • Webflow: https://webflow.com/ Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed.

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

• 0:00Speaker 00

  My aha moment of the value of first principles thinking was when I was at Dropbox. We would hire a ton of like really smart people that had never done sales and had them do sales. There are a lot of disadvantages to that, but I do think it led to a ton of innovation. That's how we got our very innovative go to market motions. Cause a lot of those people then moved into different functions at the company. They had all this context on who the user was. They had talked to so many different users at that point. If you take people that are just super smart, they've never done it before. One advantage of that is they can like innovate because they also, I think they come in with, I don't know anything. Let me just like figure this out.

• 0:38Lenny Rachitsky?

  Welcome to Lenny's podcast where I interview world-class product leaders and growth experts to learn from their hard-won experiences, building and growing today's most successful products. Today, my guest is Melissa Tan. Melissa was the longtime head of growth for Dropbox's B2B business. She was also their first growth product manager. Then she went on to do full-time advising for companies like Canva, Grammarly, Miro and Rho, helping them with their growth strategy and helping them build their growth teams. For the past two and a half years, she's been leading growth at Webflow. But hot off the presses, as Melissa shares at the top of this podcast, she's going back to full-time advising life. So if you're looking for help with go-to-market plans, growth strategy, building your growth team, aligning your sales, marketing and growth efforts, she's about to become available, so definitely reach out.

• 1:22Lenny Rachitsky?

  In our conversation, we get deep into what it takes to build a high-performing team and also how to build a high-performing growth team specifically. Melissa shares advice for becoming a leader that people will follow from company to company, how to best develop your people to become the best versions of themselves. She talks about the most common ingredients of a high-performing team and what she's learned from working with companies like Canva, Grammarly, Miro, Rho, Webflow and Dropbox. We also get into how to interview product managers and she shares her actual interview process. Plus, who your first growth hire should probably be. The most common mistakes people make when they first start to invest in growth. And a real talk story of what Dropbox did right and what they did wrong in their shift to B2B.

• 2:05Lenny Rachitsky?

  There are so many golden nuggets of lessons in this episode and I'm excited to bring it to you. With that, I bring you Melissa Tan after a short word from our sponsors. Today's episode is brought to you by Assembly AI. If you're looking to build AI-powered features in your audio and video products, then you need to know about Assembly AI, which makes it easy to transcribe and understand speech at scale. What I love about Assembly AI is you can use their simple API to access the latest AI breakthroughs from top-tier research labs. Product teams that startups and enterprises are using Assembly AI to automatically transcribe and summarize phone calls and virtual meetings, detect topics in podcasts, pinpoint when sensitive content is spoken, and lots more. All of Assembly AI's models, which are accessed through their API,

• 2:50Lenny Rachitsky?

  are production-ready. So many PMs I know are considering or already building with AI, and Assembly AI is the fastest way to build with AI for audio use cases. Now's the time to check out Assembly AI, which makes it easy to bring the highest-accuracy transcription plus valuable insights to your customers, just like Spotify, Call Rail, and Writer do for theirs. Visit assemblyai.com/leni to try their API for free and start testing their models with their no-code playground. That's assemblyai.com/leni. This episode is brought to you by Mixpanel. Get deep insights into what your users are doing at every stage of the funnel at a fair price that scales as you grow. Mixpanel gives you quick answers about your users

• 3:35Lenny Rachitsky?

  from awareness to acquisition through retention. And by capturing website activity, ad data, and multi-touch attribution right in Mixpanel, you can improve every aspect of the full user funnel. Powered by first-party behavioral data instead of third-party cookies, Mixpanel is built to be more powerful and easier to use than Google Analytics. Explore plans for teams of every size and see what Mixpanel can do for you at mixpanel.com/friends/leni. And while you're at it, they're also hiring. So check it out at mixpanel.com/friends/leni.

• 4:12Lenny Rachitsky?

  Melissa, welcome to the podcast.

• 4:14Speaker 00

  Thanks, Lenny. It's great to be here.

• 4:16Lenny Rachitsky?

  I'm excited to have you on. I hear there's a big development in your career that is gonna be out by the time this podcast comes out, where you're embarking on a new adventure. I'd love to hear more about it and for folks to understand what you're doing next.

• 4:30Speaker 00

  Over the last couple of years, I've been at Webflow, building out the growth team there. I'm actually transitioning right now and I'm out right now and I'm going to go back into advising, which is something I was doing a lot of before Webflow, working, you know, having been fortunate enough to work with great companies like Canva, Grammarly, Miro, et cetera. And so that's one of my biggest passions is working with earlier-stage companies, once they found product-market fit, and helping them scale growth. And I'll be going back into advising.

• 4:59Lenny Rachitsky?

  Amazing. That's huge news because there's like a small number of people like a Melissa that is available at certain times to work with, and this is like gonna be this window. And I just want people to understand what kinds of areas do you think you're gonna focus on for folks that may need help and may want to reach out?

• 5:16Speaker 00

  I've worked with companies across many different stages. So even in the early stage, as companies are thinking about their go-to-market strategy, previously at Dropbox, I worked across sales. I also helped start their initial product growth and self-serve team for Dropbox Business. I've also overseen pricing and packaging at Webflow. So a lot of companies initially, as they're thinking about their go-to-market strategy, should they be product-led? Should they lean more into sales motion? What should the pricing and packaging look like? I've worked with earlier-stage companies and then also post-product-market fit as companies are building out growth and they want to make sure to optimize the funnel across activation, monetization, engagement, retention. I've also advised and helped growth teams. So kind

• 6:00Speaker 00

  of across stages, focus on growth and go-to-market.

• 6:03Lenny Rachitsky?

  I guess while we're at it, what's the best way to reach out as people are listening to this? They're like, oh, my God, I want to get some help on this stuff.

• 6:09Speaker 00

  Definitely. LinkedIn is a good place. I check my LinkedIn, so feel free to reach out there.

• 6:15Lenny Rachitsky?

  Great. So usually we cut that covered at the end, but I think that was gonna be helpful in case people are like, oh, I see. I see what you can help us with. So building on that, I want to focus our conversation on two specific topics that I know that you're especially strong at. One is building high-performance teams broadly. And then two is building high-performance growth teams specifically. How does that sound as a focus of our conversation?

• 6:41Speaker 00

  Yeah, let's do it.

• 6:42Lenny Rachitsky?

  Okay.

• 6:43Speaker 00

  Two topics I'm very passionate about, let's do it.

• 6:45Lenny Rachitsky?

  So before we get into it too deeply, I want to first talk about Dropbox. So you were Dropbox for four-ish years, something like that, doing a lot of their growth work. And it was in the middle of a lot of their growth spurts and things like that. And when I think Dropbox and growth, there's kind of this dichotomy I think about. On the one hand, there's just like these incredible growth loops that were this referral program, this crazy word of mouth is just like this explosive growth story of a product. And then on the other hand, there's this B2B side that from an outsider just feels like that's something that didn't work for a long time. And then Box came around and did that really well. And I think Dropbox has done better since then, but it feels like this combination of really successful growth and then maybe less successful.

• 7:27Lenny Rachitsky?

  So I'm curious, just looking back from your experience and from what you've heard, what do you think they did, Dropbox did right? And what do you think they did wrong? And then just like, what are some learnings from that experience and watching Dropbox go through that?

• 7:39Speaker 00

  Yeah, yeah, it's a great question. And having been at Dropbox for close to five years, I did a lot of reflection while I was there. So I was there from 2013 to 2017, around like 200 people. I think about a billion dollar valuation to essentially, I think when I left, we were 1,500 people and we're valued at 10 billion at the IPO. I think the things that Dropbox got right, one of them was definitely hiring. So when I think about 2013, Dropbox was actually known in kind of the tech circles as a place that was like very selective, very difficult to get into. You could have an amazing resume and Dropbox was really selective about the type of people they brought in. So I think they looked for like two main things. They looked for first principles thinkers.

• 8:23Speaker 00

  So not necessarily your experience, but how do you approach problems? How do you know the right questions to ask? And then create your own framework around that. Dropbox also hired for people that were just really humble, collaborative and team oriented. And the combination of those two things, people that were just first principle thinkers, also just really collaborative led to tons of innovation. And so when you think about freemium product led to growth, even we created a high velocity sales motion there, there was just so much innovation because you had these folks that were just knew how to solve problems or, you know, and worked really well cross functionally, across product, growth, sales, et cetera.

• 9:04Speaker 00

  And also, you know, broadly speaking, the company just infused the topic of hiring and recruiting into the culture. It was something that as I was there, everyone knew we were all going to be spending a ton of time interviewing. We all were trained on how to sell Dropbox and how to sell the roles we were recruiting for too, so that we could close top talent. So I think that's something we definitely got right and I learned a ton about. The other thing was like the importance of execution. So a lot of times, you know, at Dropbox, we would try something and it didn't work the first time around and it was easy to be maybe say that just doesn't work for us. Like growth, we actually had tried to do some growth experiments back in 2013 and they didn't find much traction. But what we found is, you know, the devil, I like to say the devil's in the details and the devil's in how you execute.

• 9:49Speaker 00

  And so coming back to how do we execute just a little bit differently? And, you know, some of the learnings there where I think the first time we started growth, we could have been more user centric and been a lot more hypothesis driven. We were following a lot of best practices that just didn't really apply to Dropbox. And so the way that you execute ends up really mattering. That was like the second learning. The third is just focus. I think you alluded to this. I think, you know, the kind of the blessing and the curse of early success is that you can get pulled in so many different directions and Dropbox had a consumer business, a B2B business. And I think we could have clarified what is our point of view on what the overall motion should look like?

• 10:30Speaker 00

  How do we blend and think about the journey from consumer to B2B really early on? And I think a learning was that we just started our sales motion and our enterprise a little bit later than we should have and a lot of competition caught up to us. And then finally, I think the fourth one that I really believe in is how do you engage the whole company in thinking about go to market, growth and revenue? Back in 2013 in tech, growth was kind of like this dirty word and revenue was a dirty word. And so we were like, oh, a good product should sell itself. And it wasn't until our self-serve business started to slow down that we started our team, because we realized there's a ton of opportunity in just optimizing the experience. And because we started a bit later, it always felt like growth was a layer on top of product.

• 11:16Speaker 00

  I think the best way to execute is just to have that be front and center from the start. What is our go-to-market strategy? How are we thinking about monetization and having that infused into how you think about product development? And that's something both Jay-Z, who leads product at Webflow, and myself have been really intentional as we've thought of the collaboration across product and growth. So that was definitely a learning. So I guess the four things there are just importance of hiring, execution, think about your go-to-market early on, and then how do you engage the whole company on thinking about go-to-market and growth?

• 11:50Lenny Rachitsky?

  So you said Dropbox. Essentially, there was a late investment in sales. And there's a sense, maybe product-led growth is going to take us really far. And like, I imagine like, look at Jiren at Lassian, they're just all product-led, and that's amazing. I guess, what's your current framework for when it makes sense to start leaning into sales and hiring a sales team for, say, a product-led product that is working?

• 12:12Speaker 00

  It really comes down to the product. Because initially, I think most companies are leaning heavier into sales or heavier into product-led. You're usually not doing both at the same time. And so a trend I've seen is starting product-led first. And product-led, you know, the signal is that product-led is a good motion for you is if the product is really intuitive to onboard onto. There's a low learning curve, so you don't need a human to onboard the user. Also, if there's a viral component to it, that is really what can take, like Dropbox was massively viral. And I think also about Miro or Figma, those also are very viral products. Those have a, you know, kind of the DNA of product-led.

• 12:55Speaker 00

  And initially, I think you, when you have scale, you're getting a lot of signal on. What is resonating with the user? Initially, you also don't have, it takes a while to build out the features for enterprise. And so as you're building out the product-led motion, you have probably larger companies in your self-service base. And they are often knocking on your door. This happened at Dropbox being like, I need you to build SSO for me. I need you to build all these enterprise-grade features. It's not secure enough. And so you are also collecting the list of things you need to build on the enterprise side. And so I think it's typically looking like you might start product-led, then go enterprise. And then the other direction I've seen is some companies initially are just more conducive to an enterprise and sales motion.

• 13:38Speaker 00

  Potentially, you know, you need to build custom things for these users. It's also not a bottom-up motion. Like, maybe the way you sell the product starts with, you know, the legal team or the finance team or some important stakeholder. But then a lot of companies now are trying to make that shift to make the product more accessible and go product-led. And so then you're thinking about, okay, how do I make this product simpler to onboard onto? How do I think about reaching the end user at scale? And so I think it's basically first figuring out where do you start? And then starting to invest in the area. And kind of, I guess, like, maybe lastly, knowing how the whole picture fits together. There's a lot of companies that do consumer and B2B. And I think the earlier you can figure out how they go together

• 14:22Speaker 00

  and what the paths and journeys look like, it just ends up being more seamless to the user. And, you know, um, yeah.

• 14:29Lenny Rachitsky?

  Awesome. Okay, so let me start to transition into talking about building awesome teams and high-performing teams. And something that I know about you that I've heard from other people is that you have this reputation for being a person that people follow from company to company, which is like, I don't know, the ultimate sign of, of, I don't know, retention and NPS and product-market fit as a leader and a manager. So I'm just curious, what is it that you think you do that gets people to follow you from company to company?

• 14:57Speaker 00

  I've been really fortunate. I've, I've worked with a few folks from my early Dropbox team that I've known for 10 years now, like a couple of times, in some case, three times. And I always feel so privileged that I get the opportunity to work with them again, and they have that trust and confidence in me. I, I think what it is, and it took me time to develop this, is I have a very people-focused approach to how I lead and manage. I really think the core of it is deeply caring about people. Building that trust, investing in their career development, helping them figure out where they want to go in their career. I think for me, it's very personal. I have been really fortunate to have great mentors and managers that helped me in those respects. And so it really started

• 15:41Speaker 00

  from just paying it forward and wanting to do the same thing for other people that were on my team. I think it just comes down to deeply caring and everything, all your actions follow through from there. So that's, that's how I would describe that.

• 15:55Lenny Rachitsky?

  Some people may be hearing that and feel like there's this like choice you have to make as a leader, deeply care about the person or drive impact, focus on getting the work done. Do you find that those can coexist? Or is it this kind of two ends of a spectrum? And maybe the question is just like, how do you do both? How do you help people

• 16:12Speaker 00

  Yes.

• 16:12Lenny Rachitsky?

  achieve and drive impact while also feeling like you really care about them?

• 16:15Speaker 00

  I don't think that they're mutually exclusive of each other, because I think the other thing that I really emphasize on my team is being very results oriented. So as a growth leader, for better or for worse, everything you do is very measurable. And so I actually think this is why a lot of folks on my team, something that they actually appreciate is knowing what success looks like and knowing how they'll be measured. And I actually create a very results oriented culture on the team where it's clear what our goals are. We break it down into the individual levers. It's clear how success is measured for each individual. And so I don't think they are mutually exclusive. And then my role as a leader is also supporting

• 17:00Speaker 00

  their career growth, helping them meet those goals and giving them feedback along the way. So even though they might sound like two different things, I actually think they can coexist. And for me, I actually really lean into both.

• 17:15Lenny Rachitsky?

  What's an example of caring deeply about someone and being that kind of leader? People may be listening and are like, oh, yeah, I care a lot about my, my reports. But like, what are some examples of what that means to you that maybe would surprise people?

• 17:28Speaker 00

  An example from someone that they joined my team and I just early on thought that they weren't maybe moving quickly enough and they needed some more direction. And so really early into them joining the company, that was about two or three weeks in, I actually pulled them aside and I said, "Hey, we need to move a lot faster. This is where we need to get to by X. We're a growth team. We need to prove wins out early. This is how I think we should do it. Let's try to create a roadmap, a list of problems to solve, et cetera, hypotheses." And they don't have to be right, but just getting something out there, starting to line the whole team on what those are, and then defining how we're going to measure success and know where we're in the right path.

• 18:10Speaker 00

  We just need to get there as quickly as we can. And so I gave them that feedback and afterwards, you know, ever since then, they have been just like on a tear. And they actually have mentioned that in later conversations, a year into working together, that they were so grateful that I had that conversation with them and that I took the time to tell them those things. I think sometimes as a manager, it can maybe, you know, you want to avoid the uncomfortable conversations, but I actually think the more direct you can be, but also saying, "This is my intention. My intention is to set you up for success." That goes really far. And I think that's a great example

• 18:50Speaker 00

  of how do you, you know, deeply care about somebody and give them direct feedback and you're giving them direct feedback because you deeply care and you also believe that they can do things differently, right? I think the only reason you'd give that feedback is because you know they could do things differently and you just want to help support them.

• 19:07Lenny Rachitsky?

  In that conversation, what is it that you did that made them feel like you really cared about them? Because when I hear you describe it, it's like you're just telling him, you're giving him feedback, just like, "Hey, you need to do a lot better at this. We need to actually hit our goals." What was it that made them feel like, "Oh, she really wants me to succeed?"

• 19:22Speaker 00

  I think in that conversation, what's important is also saying, I believe you can do all these things and I'm doing this to support you, or I'm sharing this feedback because I believe in you. Also saying that I'm here as support, like as you are building that out, let me know what I can do to support you. We can jam on it together if it's helpful. Basically, I guess, like boiling it down to like one, restating your intention and why you are having that conversation, to sharing that you are there to support them and offering your, your own help as well. Those I think are the things that go along well. And I think the, the third thing is, as you give someone

• 20:07Speaker 00

  feedback, it should never sound like finger pointing or criticizing. It's really just, hey, this is what I observed. This is the impact that it had. And here is like a different way. And so keeping the feedback really about the work itself and the things that, that the specific things that you think can be improved.

• 20:27Lenny Rachitsky?

  I know you're also a big fan of developing talent internally versus hiring, you know, experts from the outside. And it's always this like decision, I think, as a leader and as a company, like how much do you invest in developing people, knowing they can leave anytime, knowing that that's going to take all this time and work? What have you found from and just learned about the advantages maybe of spending time in developing people and helping them progress? And just why is that something you find really important?

• 20:54Speaker 00

  I'll start with the why behind developing people. For me personally, it comes from like, I'm personally passionate about it just because I feel that a lot of folks invested in me. Personally, when I started out in the working world, I actually struggled quite a lot. I mean, making the transition from school where it's really clear what success looks like, you're just studying, getting great, good grades to work where things are much more ambiguous was a really big transition for me. And I really benefited from so many mentors that invested in me that I kept in touch with over the years that have also just helped me with my careers. You know, two that really stand out are from Dropbox, Oliver J, who goes by OJ, and GC Leonetti.

• 21:36Speaker 00

  So it really has come from a very personal place for me. Secondly, I think it's just makes a lot of sense as you're scaling a company, that as you are growing, it just is a smoother transition that the folks on your team can grow with you. People will build institutional knowledge. I think people talk a lot about founder intuition and that intuition that founders just have. I actually think that extends to early employees too, that have built a ton of context on the user, on how to get things done at the company. So the more that you develop talent within the company, the smoother your transition is versus bringing someone from the outside where there's just a lot of different factors and there's risk there. And so it really comes from a personal place, but also it makes a lot of

• 22:21Speaker 00

  sense from just like de-risking the situation as you're scaling.

• 22:27Lenny Rachitsky?

  In my personal career, I had the biggest inflection point and the most progress I made as a product manager was one manager who just did exactly what you're describing, where you invested really deeply in helping me become a better PM. And it was not easy. He was just like very critical of all the things I wasn't doing perfectly. And I always think about people don't sometimes have someone like that in their career. They don't have a manager like a Melissa. Do you have any advice for a few people that are looking for someone like that, or they're just like, man, I have no one around me that's really helping me develop? What do you suggest they do?

• 22:58Speaker 00

  As you are looking for a job, I actually do think you should look to work with people that have that reputation and that you can see that interest, that they enjoy mentoring people. They have a track record of developing people. Maybe they have brought other people they've worked with at the company from other companies. Those are good signals that that's something that that person cares about. And, you know, even in the interview process, asking, kind of interviewing your manager too, and understanding what is their management philosophy? How do they think about your career path in that role? Those are things I would look for. The second thing too is, as you're interviewing, looking for a manager who, especially your

• 23:39Speaker 00

  success will be tied to their success. This is actually what happened. I mean, you know, it's not like you need to be super strategic about that, but I, when I reflect back at times when I got closest to people was when I was one of the most critical people on their team and they really needed me to be successful. And so they also just would spend a ton more time with me, right? So really looking for those opportunities and being really selective in the types of roles you're taking. I also think there have been times for me personally where I've built relationships with someone that wasn't my direct manager that worked at the same company. And this actually has happened a lot at other companies I've worked with where someone knows that it's a passion of mine to mentor people. And so they proactively reach out to me, ask me for advice, ask me, hey, can we set up

• 24:23Speaker 00

  a monthly recurring sync? And so I also think you can look for other people at the company that you work with. And then finally, the other thing is looking for like external advisors. I actually, in my advising, end up mentoring a lot of the people that I work with too. It just organically ends up happening. And so I would say, summarize that is just look for the people that you think have this passion, build that relationship with them. And ideally, I think you actually build the strongest when you are working together. You just learn so much about each other. But if you don't have that set up, I think there's other ways to just proactively look for mentorship and guidance.

• 25:00Lenny Rachitsky?

  Any tips on the questions maybe to ask a manager to help get to this? If any come to mind? And also, when you're looking for someone to help you, anything specific you think that people should look for that maybe they may not be thinking about?

• 25:12Speaker 00

  On the questions to ask when you're interviewing for a role, I would actually ask things like, I'd love to get a sense for how you think about, I mean, I think you can flat out ask, I'd like to get a sense of how you think about managing folks on your team, how you think about developing talent on your team and seeing what their response is to that. I would also ask, how are you thinking about the career path for this role? And if the person has not thought about it at all, or doesn't ask you, well, what is important to you? I think those are some signals that it's maybe not where this person tends to spend their time thinking. And then I would also ask other people on the panel that are not going to be your manager,

• 25:57Speaker 00

  but that work with this person, especially if you happen to talk to people that they manage. How is this person as a manager? And that ends up being also very insightful. The questions I would ask if you're looking for someone external, I always find that that relationship is best the more organic it could be. I think Sheryl Sandberg wrote this in her book Lean In. She writes like one, she basically writes about how some people will go, will you be my mentor? And I've got that question too, and it's just a lot of pressure like to get asked that question really early in, and you don't really know the person.

• 26:37Speaker 00

  And so the more it can be organic where you talk to somebody, you have actual advice that you want. Like some people will just reach out to me that I haven't worked with in a long time. And like, hey, I'm thinking about a career decision or I'm in this tricky situation at work. Can we talk? And I just give them advice and they will reach out to me for advice occasionally. It doesn't have to be a recurring thing that you have to just nurture that relationship. I think that is a way to do it. Or if you are working with somebody and you want to set up some type of monthly thing, I think you can ask for that as well. The only thing is I would just be respectful of the time. So if you don't have anything to talk about that month or anything like that, I'm just always willing to help people. It doesn't mean we have to be frequently in touch.

• 27:18Speaker 00

  And so I think it's also less about being frequently in touch and it's just going and reaching out when you actually have a problem. People that want to help others are just gonna, if they have the time, they'll, they'll say yes.

• 27:30Lenny Rachitsky?

  Tim Ferriss talks about that too. He's like, never ask someone to be your mentor. As you said, that's a scary proposition. You're committing to something, it's, it's pressure versus just like, hey, can we just meet? And can I just get some advice? And, and then maybe after you do that, can we meet next month also? And just kind of help it grow organically.

• 27:48Speaker 00

  Yeah, definitely.

• 27:50Lenny Rachitsky?

  I want to talk about how you develop talent and what you've learned there. But before that, I wanted to zoom out maybe first and talk about ingredients of high performance teams. So before I ask that question, could you just list the companies you've worked with? Some of the companies you've worked with?

• 28:03Speaker 00

  I guess I've mentioned Dropbox. So Dropbox was my first high-growth tech startup. And then after Dropbox, I did a lot of advising. So I got to work with Typeform in Barcelona. And then someone at Typeform introduced me to Canva. So I met Canva when they were still about 200 people in their early growth journey. Have worked with Grammarly. Miro and then a joint Webflow and so have been fortunate to be part of a ton of, I guess, what I would think are high performing teams.

• 28:33Lenny Rachitsky?

  100%. That's an incredible roster. So here's the question, what are some of the most common ingredients you've seen across these teams, which from an outsider's perspective, seem quite high performing?

• 28:45Speaker 00

  I think it first starts with the team having a really clear, really clear goals. They need to know what success looks like and often I think that's for growth teams in particular, it's always really clear, hey, we need to hit certain metrics, we have certain goals for the quarter and for the year. And then also having a mission. So the mission's all about the why, right? So an example at Webflow is we have our growth team gold on ultimately the North Star is ARR, annual recurring revenue, and then you break it down into the levers that drive ARR, the leading indicator. So that could be activation rates, the number of customers you bring in, et cetera. And so each team has really clear goals and then we have our mission, the why.

• 29:27Speaker 00

  Our mission, the why behind why we do it is we want to build these delightful experiences for our users. We want to support them on their journey on the product. And the reason why the what is monetization is that's just a good signal that people find your product valuable, especially if they're consistently paying you and they're retaining. And then the other thing that I think is important is culture. So how are you going to do these things? When thinking about culture, obviously it depends on the function and the culture you want to set there. For me personally, the type of culture I try to set for the team is one around being really results oriented. So something that someone on my team was saying the other day is you always make it really clear that we're going to be measured on impact

• 30:09Speaker 00

  and that's like how we are ultimately measured as a team. And so really creating that results oriented team, also a team that's very team first and collaborative. I think when you have very clear goals, when it's very results oriented, you could potentially be in a situation where people feel they're competing against each other and you just don't want that. You actually want folks on the team to help each other out, to share learnings. I think that's what ends up being like a situation where one plus one equals three. You're not locally optimizing, but you're thinking broader about the team and thinking beyond yourself. The third thing is really this ownership mentality.

• 30:46Speaker 00

  Something I directly saw at Dropbox is when we were a smaller company, everyone just felt a lot more ownership and accountability because there's just nobody else. You're wearing like five different hats, you have to do it. As you scale, it's really easy to suddenly feel like that ownership is diluted. And so something I always try to keep in the team, it's the feeling that we're owners and that really proactive mindset of like, how am I going to solve this problem? I'm blocked by this team, what am I going to do about it? And just being people that have strong sense of agency. And then lastly, having fun. I, I think that it's easy at work to, especially, you know, in, in high pressured environments, easy to get stressed and, and all that stuff. And at the end of the day, I think the, the more fun, this is very personal to me,

• 31:31Speaker 00

  but the more fun you can have, the, the better everything is. And so just making sure you're infusing fun along the way and you're not taking things too seriously.

• 31:38Lenny Rachitsky?

  So I was taking notes as you were talking and there's kind of these four items. Just to summarize, one is creating a culture of impact and performance. Two is being team first and making about the team versus the person. Three is creating a sense of ownership and making people feel like they're owners. And then having fun, which I love. A question I have there is say, within the ownership bucket of creating a sense of ownership,

• 32:01Lenny Rachitsky?

  what do you actually do to create that sense amongst the team?

• 32:04Speaker 00

  I think it first starts with defining the scope that everyone is going to own and drive. Right? So as you are setting up the team, it's important that each person on the team has scope that they can run independently and that they are excited to own and drive. So one example here is as I was leaving Dropbox, the finance team looked at our metrics and saw that each growth PM was bringing over a million in ARR per year, just for all the experiments. Yeah. And so that's quite a lot of impact. And being a finance team, they said logically, we should just double the team. Like if each person brings in more than a million, if we want to double the ARR, let's just double the team. And so I actually pushed back significantly, though I thought to myself,

• 32:47Speaker 00

  if we double the team, what is everyone on the team going to own and drive? Is it like we split up different parts of the website, different parts of the product? One PM owns just like the checkout flow. I didn't think that was going to be interesting enough for the team and gonna help us recruit people that were excited to solve such small parts of the of the growth problem. And so really thinking about how do you carve out scope? And you know, if you are a growth team, maybe thinking about splitting up by problems to solve that are really meaty, by areas of the funnel, like activation, monetization, et cetera. So first, starting out with carving out good scope. And then the second thing is just infusing a culture of thinking like an owner. This infusing of the culture, I think it comes out in a few ways.

• 33:30Speaker 00

  One is, and this is really common in growth, growth is so cross-functional that you often will end up feeling like you're blocked by other teams. Let's say we want to run an experiment on this part of the product. Maybe that it's a core PM that kind of owns that service area that doesn't want to drive that thing. Or let's say we're blocked by a bottleneck on designer engineering. It it's something where I think if you're thinking like an owner, you're not feeling like easily disempowered because you can't do something. And instead, you're thinking, what is everything I I can do? And did I exhaust all the options? And then finally, it's it's leading by example. I try to also show to my team that I'm always thinking like an owner and that I'm always trying to do everything I can.

• 34:14Speaker 00

  And finally, like as a leader, thinking like an owner also means taking responsibility for your team. And so if things don't go right in my team, I'm the first one to say that ultimately I'm responsible and it's a failure or oversight on my side. And so that is what I think an ownership mentality is. It's just really thinking about the scope, creating that culture. And then as a leader, it's just seeing yourself as ultimately being accountable.

• 34:37Lenny Rachitsky?

  Awesome. And this connects to something else I wanted to pull the thread on, which is the team first bucket. I think about Meta, not to like throw them under the bus or anything, but I feel like everyone I know at Meta, their their performance review is very tied to their impact. It's like very impact driven and that leads to people needing to drive impact themselves. Like I drove this impact and they look at like, how much did you contribute to that impact versus other people on your team? And it creates some challenges, I think, for people. How do you create that feeling of team first? Even though your performance, as you talked about, is so tied to here's your success metric, here's what success means for you, for the team. How do you make it feel team first versus like, I need to do this myself?

• 35:17Speaker 00

  There's definitely a delicate balance here. It comes down to the way that I think the manager leads the team and sets the tone. And so for me, I always make it clear that even though results are important, it's a team sport. And so I often find that I am encouraging the team to work together. So I, like, again, as a leader, you have context and everything happening. So sometimes I know one PM is working on something or even a PM outside our team is working on something and I try to actually fill in context if I think someone on my team could contribute. And I encourage that action, even though it doesn't maybe feed into impact on the thing they're driving.

• 36:01Speaker 00

  So it really comes down to the culture that you set and what you encourage the team to do. I also think the more that you can see that you actually benefit from helping each other out, the better it is. And, and finally, I think, again, leading by example, because I actually am very team first, I'm often actually helping other teams and doing things that might not ultimately benefit or be part of my scope. You know, a good example here is I was actually driving pricing and packaging at Webflow for a very long time, just because no one at the company was driving it and it was a huge opportunity area that, and I actually was doing it for enterprise pricing too. And so even though I'm overseeing self-serve, I was actually supporting enterprise pricing and packaging.

• 36:46Speaker 00

  And so I also showed to my team, hey, I'm also doing all these things to help the company. And I think that is what helped set that tone and that culture.

• 36:55Lenny Rachitsky?

  How do you then avoid doing too much work? I think there's also this challenge of people being too good at too many things. And then they end up doing so many things and then they burn out. Do you have any rules of thumb or lessons there?

• 37:05Speaker 00

  I think for me, it's been a learning journey too. I've actually gotten feedback on that very thing for my team that like Melissa sometimes taking on too much or trying to do too much. And so I think it's a delicate balance. If we're talking about the person individually, you have to know what your limits are. And you also can do things in spurts, but it's important to know ultimately what you can take on. Also putting, I find that putting a specific timeline like, hey, I'm going to do this thing for a quarter. But after that, we really need to find somebody else to do it or hand it off is really helpful. It's definitely a delicate balance. I do think it's a great question because I think that's a common thing people early in their careers struggle with, which is they can lose focus because they're trying to help everybody.

• 37:49Speaker 00

  That was actually a problem I had when I first joined Dropbox is I was the only sales ops person. So I was just helping every sales leader with their metrics and very hot focus. And so it is a little bit of trial and error. I think the most important thing is to not be so overly focused on just what you're doing and try to help others. But then knowing that there are certain things that just can't drop. And if you start to see things that are starting to drop that you're ultimately responsible for, that's a signal that you're, you're taking on too much.

• 38:18Lenny Rachitsky?

  This episode is brought to you by Epo. Epo is a next generation A B testing platform built by Airbnb alums for modern growth teams. Companies like DraftKings, Zapier, ClickUp, Twitch and Cameo rely on Epo to power their experiments. Wherever you work, running experiments is increasingly essential, but there are no commercial tools that integrate with a modern growth team stack. This leads to wasted time building internal tools or trying to run your own experiments through a clunky marketing tool. When I was at Airbnb, one of the things that I loved most about working there was our experimentation platform, where I was able to slice and dice data by device types, country, user stage. Epo does all that and more, delivering results quickly, avoiding annoying prolonged analytic cycles and helping you easily get to the root cause of any issue you discover.

• 39:03Lenny Rachitsky?

  Epo lets you go. Beyond basic click through metrics and instead use your North Star metrics like activation, retention, subscription and payments. Eppo supports tests on the front end, on the back end, email marketing, even machine learning claims. Check out Eppo at get E P P O dot com. That's get Eppo dot com and 10x your experiment velocity. Let's come back to the developing talent bucket. I would kind of went on a tangent, but I want to come back to that. So we talked about why you're excited about developing talent, the benefits you've experienced. I'm curious what you actually do to help people become better product managers, leaders of all kind. What actually has, have you seen works?

• 39:42Speaker 00

  In terms of developing talent, I think of this as like stages of, of the life cycle of your relationship. Right? So I think at first actually starts, this is very meta as a growth person, starts with when you hire somebody, really making sure you're finding somebody that is a good fit for the role. It's a good mutual fit. I also tend to look for folks that have a growth mindset. There are people that are wanting to learn. They're looking for feedback. They take feedback well. And then after that, they join the company and as a manager, my job is to help set them up for success. So how do I ramp them up as quickly as possible, connect them to the right people at the company?

• 40:24Speaker 00

  How do I also make sure it's clear what success looks like in their first 90 days? And then how do I help them like secure early wins essentially? So I often will suggest, hey, you should do this presentation. It's a great way to get visibility early in your, in your journey here. Here are some like things where there's like low hanging fruit or even rotting fruit that you should take on and to secure early wins. Then in your journey, I think it's a lot about just giving feedback along the way, making sure you give visibility. One recent hack I have is having folks on the team create looms that they can share with different leaders at Webflow. You know, it's hard to sometimes get visibility and get live meeting calendars. But if you create like a five or 10 minute loom on something you did, that's just a great way to get visibility.

• 41:10Speaker 00

  And then finally, I think it's that lifelong relationship actually. So I'm still in touch with a lot of people that I've managed and I've helped them, you know, whether it's they're looking for their new job or they have career advice, I always make myself available. And so it's actually that lifelong journey of just developing that person. And at some point it's not, you know, it's not even. Developing that person, but it's like having a friendship with somebody and I feel like I've learned a ton from people that I have managed. And so it ends up being this really great thing where you initially started working together, but you now know each other so well. And I think that's even how I've developed as a manager is just getting feedback from my team.

• 41:51Lenny Rachitsky?

  This all comes back to something you mentioned a couple of times earlier, which is caring a lot about the person that you work with. Your approach also reminds me of this book Radical Candor. I imagine you're a fan and that's kind of the way you think about it.

• 42:03Speaker 00

  Yeah, definitely. Interestingly enough, Kim Scott was at Dropbox for a short period of time. So when I, when I joined Dropbox, she was actually on my interview panel and we overlapped for three months. And she actually workedshopped that book with our team before, or before she published it. And that always resonated with me. And I remember her saying, you know, you have to, um, I forget the exact words, but it's essentially like be direct, but deeply care.

• 42:30Lenny Rachitsky?

  Yeah, care deeply, but uh, something directly challenged directly, something like.

• 42:35Speaker 00

  Yeah, care deeply, but challenge directly. And that has always been something that is something I try to infuse and has really inspired me as a leader.

• 42:44Lenny Rachitsky?

  We're gonna link to that book if folks don't know about it. I love it. You talked about hiring PMs and how that is important in building high performing teams. So let's spend a little time there and maybe just two questions all throughout and you can approach them however you want. One is just what do you look for when you're hiring product managers? You've hired a lot of PMs. You've managed a lot of PMs over the years. What do you look for, especially things that maybe other people don't focus on enough? And then just what is your interview process like? What do you find is most helpful for interviewing process wise?

• 43:11Speaker 00

  In terms of what I look for, I think there's like a kind of this kind of known list of things that you probably want to look for, for a PM that I probably are not gonna, I'm not gonna say anything groundbreaking here, but you know, obviously communication skills, the ability to manage stakeholders and work well cross functionally. The things that I lean especially heavy on in my interview process is this concept of first principles thinking or strong critical thinking. So usually there's some live problem solving component to my interview process where I really lean more heavily into how would you approach X problem? And then I dig into the why and try to understand why would they approach it this way? See what questions they're asking and just see how they approach problem solving.

• 43:55Speaker 00

  And then the other thing that I look for that I mentioned is that growth mindset. So really seeing how does this person take feedback? And so I will actually sometimes give feedback to candidates through the process. Something that I do that I learned a few years ago that was super helpful is I, so I always have a presentation component to the interview process that checks for prepared thinking, communication, and I recommend a prep call between the two, the two of us before that presentation. And I actually will give feedback on the presentation. And what this gives me signal is what is it actually going to be like to work together? And then I see how they incorporate it into the final product. And that is always really interesting and sometimes is the biggest signal to what it's going to be like to work with this person.

• 44:39Lenny Rachitsky?

  Okay, this is great. I want to spend a little time here. So what is the actual sequence that you recommend or you use for interviewing? There's a presentation, there's a prep call, what else is kind of involved in that?

• 44:49Speaker 00

  Usually, you know, hiring manager screen, and I actually do the live problem solving at this screen. I actually think it weeds out the most people. And there's actually two things I do here. One is a live problem solver. How would you approach X? So let's say I'm hiring for pricing at Webflow. I would ask how like, how would you approach pricing? I sometimes would say, hey, do you have your laptop? Can you pull up our pricing page? Curious to get your thoughts. What would you want to change? That was a trick I learned at Dropbox where we would actually pull up the Dropbox website and be like, hey, what'd you want to test here? Why? And you get a ton of signal on how they approach the problem, how they think. I ask why a bunch. And then the next screen is talking to more folks at the team that test for different competencies.

• 45:32Speaker 00

  And depending on what you're hiring for, we just have each person focus on a different competency. And it also depends on the role. So some roles are more technical, some require working more closely with different stakeholders. So you want to make sure you can test those things. And then the final round is the presentation and then also maybe a conversation on other areas. We want that like have come through the interview process. We want to dig in further. The presentation is usually thinking through how you'd approach. You're collecting all this information on the company or the problem throughout the interview process. And so it culminates in what do you think this should look like? Or maybe what would you want to do in your first 90 days? It depends on the role, but it's usually some type of presentation about the problem you would be working on at the company.

• 46:18Speaker 00

  Before that, we have that that preparation call with me where often candidates will have questions like, "Oh, I I need to know this data," or "I'm curious about X." And so it's really just a call to help them. And then at this stage, too, they'll often have the actual draft of the presentation. And so we'll go through it together. And I'll actually be like, "Hey, I think you should lean in heavier here. How would you think about this?" I'll even say, for example, at Webflow, I'll be like, "We're thinking about XYZ thing, just so you know, and maybe incorporating that into your presentation would be really helpful." And so that's where I get a lot of signal of what is it going to be like to work with this person on a presentation? And then I'll see in the presentation whether they incorporate it or not, or how they did.

• 47:01Speaker 00

  And sometimes I've seen candidates that didn't incorporate any of it. And I and I kind of am like, "Okay, this is like, probably not a fit." And it actually, I think that other thing about that call is it helps just set the candidate up for success, right? It's actually quite a lot of work to create a presentation. The more we can help them by giving them information, making sure they can be successful, it's helpful. And I and I think, I guess, lastly, it gives them a taste of what it's like to work with me.

• 47:26Lenny Rachitsky?

  I've never heard of that step before. That is really interesting. They actually give them feedback before they present. I imagine they're like, "What the hell is going on here? I thought I was trying to show them what I can do, not like they're going to help me do a great job." That is really interesting. Uh, maybe two very logistical questions there. How much time do you give them to work on this presentation? And then, too, you said that you ask some questions related to the actual problem they're solving versus a theoretical problem. Um, so those are the two questions, I guess.

• 47:52Speaker 00

  Typically, we will schedule it about a week in advance. They have a week. The tricky thing here is, obviously, it's a big ask to ask someone to create a presentation. And so if it's one week, that's like, long enough to create it, but it's short enough that you don't spend tons of time. The other thing is just making it clear, like, "Don't exceed more than X number of slides." In Webflow's case, we've done, like, "Don't exceed more than 30 slides." And that's like, quite a lot. "We do not expect you to do 30 slides." And then the other thing I make sure to emphasize is it's really about wanting to know how you'd approach it. So don't worry about the slides. Be able to talk to it and have what you need to talk to it, because we're actually just looking for the substance.

• 48:34Speaker 00

  And so that's how much time we give them. And it's usually a 30-minute presentation with 15-minute Q and A. The second part of your question was, yeah, so in terms of picking the topic... So there's a few ways to think about it. I know some folks will be like, oh, we have candidates present on something they've worked with in the past. I've tried that form and it's really difficult because I found that candidates even sometimes spend tons of time sharing the context of that company. And then also, it doesn't really give a sense of, because as you're interviewing from a role, you're getting a ton of context on the actual company and the problem. And so it also is testing for how much did they pick up along the way?

• 49:18Speaker 00

  Do they also, would they like working on this area once they join? And so there are some candidates that sometimes are concerned about the amount of time they would spend on it, or say like, I'm going to have to, this is going to be a big lift. And definitely mindful of that. I think the main thing though is it is actually in the candidate's best interest to kind of understand what they're going to work on and start to understand, like, for example, there are some candidates that have gone through the, far through the process and haven't worked in the Webflow product very much. And I always think that's an interesting flag because if you aren't in the product a lot, you're not going to get good context on whether you like it or not. And so I actually think it's almost even in the best interest of the candidate to go much deeper.

• 49:58Lenny Rachitsky?

  I could spend like another hour talking about interview strategy, but I want to make sure we have time for the growth team stuff. So let's transition to that. And my first question here is, you've worked with a lot of different teams, a lot of different companies on helping them figure out their growth strategy, hiring their growth teams, just kind of figuring out growth. I'm curious what the most common pitfalls and mistakes you've seen across companies trying to figure out growth and build growth teams.

• 50:26Speaker 00

  One of the most common pitfalls, I'd say, is not having, and I've alluded to this, not having a sense of the big picture from the start and not being strategic about what your go-to-market strategy is going to be. Also, what is your pricing and packaging going to look like? So I wrote actually an article for the YC blog a few years ago with With Abby Kuzmanoff, who was on my team at Dropbox, about this because I felt like even at Dropbox, we were hap- we were, I mean, it's a great thing. We were haphazardly finding amazing things. We had a freemium consumer product. Then we realized people wanted a Teams product, so we built a Teams product, but we never created that whole blueprint of like, what should it look like? And what are the different connection points across consumer business?

• 51:10Speaker 00

  What should our model look like? I've also seen companies that maybe weren't intentional enough about pricing from the start. And so think about what is the value metric? And then they have to, you know, they've already have massive scale and then they're rethinking their pricing. That's actually quite a big headache to actually think about, okay, how do, you know, do we grandfather users? How do we bring the legacy customers onto our new pricing? And so thinking about your pricing from the start is important. They might go to market from the start is important. The other thing I have seen a lot is just like, again, this goes back to learning from Dropbox is the execution.

• 51:48Speaker 00

  Folks, you know, taking a class or reading a lot about growth and trying to do the same thing and not really actually starting from first, let's look at our data, let's talk to our customers. What do we think are the biggest hypotheses? And starting your experiments based on your own data and right sizing the experiment. I think sometimes teams are experimenting on things that are too small, that aren't going to move the needle because they heard it was really successful company X. But that company X might be a Dropbox where every 0.5% improvement in conversion makes a difference. But if you're early stage, it doesn't matter and you need to actually think bigger. The other thing is the opposite problem. Redoing a whole thing, but not having a hypothesis.

• 52:32Speaker 00

  This was an early mistake I made at Dropbox where I redid the checkout page to something that I thought was like better UX. But then I changed so many different components that it was like, even when it failed, it was unclear why it failed. So really distilling it to hypotheses. And then the last thing I would say is figuring out what I call the flying formation of how the different growth teams will work with other companies. And again, I alluded to this, but growth shouldn't feel like it's a layer on top. And a lot of things, the things that are tricky early on is figuring out how you work with other teams. I think the best or the ideal way to work is to have growth infused in the company.

• 53:14Speaker 00

  And so an example here is often the growth team is going to be potentially the closest to the user. They're going to get a lot of feedback. They're going to hear directly from the user. As a growth team, I think one of the big values that we can have is actually giving that feedback back to other teams at the company. And so even as a growth team, can we help inform the product roadmap? Also, like on the reverse, thinking about, you know, as PMs, how can PMs be more growth oriented as well?

• 53:43Lenny Rachitsky?

  I like this term flying formation. I've never heard of this before. What is that exactly? Again, is that just like how growth is integrated within the company?

• 53:51Speaker 00

  Yeah, I guess flying formation, um, essentially I don't know where it comes from. I guess it's maybe like a, maybe it's a military term or something.

• 53:59Lenny Rachitsky?

  I can see that. Yeah, like the Blue Angels.

• 54:00Speaker 00

  Work together? Yeah, yeah. I, I think of flying formation as like, how do we work together across teams? You also can think of it as like a D C too, like driver accountable contributor informed. I think sometimes when you don't know how you're going to work together, you end up like stepping over each other's toes. You're unclear. Who is the decision maker here? Who did we need to work with at what point in the journey? And so the flying formation, what I think it is, is part of it is a D C of like, what are the different roles?

• 54:32Lenny Rachitsky?

  Can you define that actually? Cause a lot of people probably won't know that term.

• 54:35Speaker 00

  A D C is a framework to think about the different roles on the team, on a project, right? Or an area. So D stands for driver. This is the person driving the project. A is accountable. This is the person that's ultimately accountable and is often the final decision maker. If there's any open questions. C is contributor. These are all the different teams that are going to contribute. And then I is informed. These are the people that need to be informed, but they're not directly contributing. They're not a decision maker and part of the project. And so it's a nice, simple framework for when you are working across teams and it needs to be clear who is in what role.

• 55:15Speaker 00

  And the area that tends to be the most confusing can be the accountable and who the decision maker is. It can be easy to have lots of teams and then it's unclear. How do we get to a decision? Ultimately, and who should make that decision? And that person should often be the person that has the most context or is ultimately responsible. And so I think the flying formation has this D C. I often also put operating rhythms in it. So it's clear like what is happening at what point. And so we created a flying formation when we were first starting the growth team at Webflow and we were trying to figure out how does product growth work with product? How does product growth work with growth marketing? What are the different cadences that each team has? And so very tactically, we put a doc together to say, okay,

• 55:58Speaker 00

  product growth is accountable for all the metrics downstream of signups. Growth marketing is accountable for signups. They're also driving or like have goals around CAC, the customer acquisition costs. And these are the different metrics everyone owns. We have a weekly meeting where we look at the metrics together. We also will do updates around the room to talk about initiatives and identify areas we want to work with. And then we also think through quarterly planning where we're each identifying projects that we're driving. There are some projects that we might also work on together. And so it's that essentially that meeting cadence that you're going to have, the operating rhythms, that that's essentially how I think about a flying formation.

• 56:40Lenny Rachitsky?

  I love it. That would make a great blog post. By the way, if you're looking for some to write, an example of your actual flying formation at Webflow, I think people would love that.

• 56:48Speaker 00

  Yeah.

• 56:48Lenny Rachitsky?

  One kind of tangent that I wanted to touch on is there's this trend of product teams owning revenue. Elena talked about this on a recent podcast. Do you have a perspective on should product growth teams own revenue and have revenue numbers as their goals or not?

• 57:04Speaker 00

  Really depends on the company and what product growth is driving. I've always, in the companies I was at, and actually even the companies I advise, the product growth team owns revenue. So it's not always the case. I've actually seen revenue owned by marketing. So marketing makes sense if it's like more top of funnel growth. I've also seen it, this is an interesting one by finance, actually. This is usually early in the company. So early at Canva, it was owned by finance and that's because finance had a view on everything happening in the business and would actually be maybe advising other teams on, hey, our conversion rates could improve. We need to do X or we're not driving, you know, signups and customers efficiently.

• 57:49Speaker 00

  But over time, it doesn't really sit in finance that has evolved and now sits under the person that is driving product growth and product. So I have seen it more often than not being owned by products. Our team at Dropbox moved a ton. Actually, we started marketing. We actually then reported into the revenue org with sales and then we finally moved into product because we realized so much of our revenue was that product growth motion happening in the product that we felt it was important that that product team owned revenue.

• 58:19Lenny Rachitsky?

  A lot of the things you're talking about are kind of based in how growth starts at a company. I imagine one of the most common questions you get is how do I start to invest in growth? How do I hire my first growth person? How do I build a team around them? It's one of those common questions I get. So let's spend a little time here. What is your advice to founders that are just starting to think about building their initial growth team and how to approach that and to look for initially and kind of think about that large?

• 58:43Speaker 00

  I get this question a lot as well. I'd say initially, when a company is starting out, the goal is getting to product market fit and figuring out who their ideal customer profile is, like their ICP. And at this point, I think everyone at the company should be thinking about growth. They're finding their first few design partners that they will co-create the product with. They're figuring out who is their product resonating with, who is maybe also the decision maker in purchasing the product. And they're figuring out, do we want kind of a bottom-up product-led motion? Are we going to lean more heavily into sales? Are we going to do both? After you reach product market fit and you're starting to get your first few customers, the first growth person I see more often than not isn't someone driving acquisition.

• 59:27Speaker 00

  You need to find your first a thousand or thousands of customers and you need to do it at scale. And so if that is the focus of the company, typically what I would recommend is somebody that, they don't need to be an expert, but they need to, ideally, they understand maybe one or two channels well and that they're the channels that you have a hypothesis you will find traction in. And I see this person a little bit like a portfolio manager, right? Because you're trying to figure out, usually companies don't have like many channels that are split evenly. It's they find one or two that really work and make up like it's 80/20 rule, it makes up 80% of where the signups are coming from. And this portfolio manager is testing different things out. They even, you know, you could leverage agencies.

• 1:00:12Speaker 00

  There are a lot of agencies out there for SEO, for paid marketing, et cetera. But they are smart enough to define, is this working? How do I do it at scale? You also want to make sure it's quality signups that are actually monetizable. And so that is a rule typically if you're hiring an acquisition of that first growth person. And then the other two areas to focus early on, but I don't think you need a dedicated person for are activation. You want to make sure as you're pouring leads into the top of funnel, you're activating users. And here, I don't think you actually need to do A B testing. Your volume isn't probably going to be strong enough. I think even just finding like five individuals that are part of your target audience, just doing user testing, set up a zoom, watch them onboard onto the product and have them talk out loud.

• 1:00:54Speaker 00

  You'll fight a lot and you can also just take best practices of like onboarding checklist, et cetera. So activation and then I've said this a lot, but pricing and packaging, really thinking about pricing. But I don't think that needs to be a dedicated person.

• 1:01:06Lenny Rachitsky?

  What kind of profile have you found to be most successful for this sort of person? Some people will look for like, I want to hire Melissa and like, let's just go, go big. The best person I can find and have them own this versus someone that just knew from school that's going to figure it out. And I guess there's somewhere in the middle. What do you find works best for that first hire?

• 1:01:25Speaker 00

  It really depends on the current makeup of the team. How much do the founders themselves or the current team, how much of an interest do they have in growth? If they have an interest in growth and it's more about finding someone to execute. I think it's finding someone that's a bit earlier in their career potentially that is just a strong first principles thinker. I think there's like hit or miss on like, I'm a former consultant. So I used to always say, find a former consultant. I do think there can be hit or miss and there is some value in folks that like actually understand acquisition and. Have done it before and so maybe have figured out certain channels. So I think you either go for someone that's done acquisition before, maybe they're a little bit earlier in their career.

• 1:02:09Speaker 00

  So they have this great growth mindset, but make sure they're a first principles thinker. The other option is like, find just a really smart person early in their career. Have them take a reforged class, have them soak up everything. And then the other option of hiring someone more experienced, I think it really depends on if you want that person to take on a lot more and be almost part of like your founding team. And do you want to find someone that is going to join your leadership team? The other option, I guess, is you could also just bring on an advisor and that advisor is someone that's not full time. It can even guide if you hire someone that's a bit earlier, guide that person. And that is like a really good combination.

• 1:02:49Speaker 00

  And so it really depends on the context, who's also on the current team and who you want to bring into. Like, are you looking for an actual leader that's going to scale with the company? Or, you know, are you not ready quite yet for that?

• 1:03:03Lenny Rachitsky?

  What about in terms of their skillset? I imagine if you're kind of feeling like paid growth is going to be your main acquisition channel, you probably want to find someone that's really good at that versus it might be morality, product led growth stuff. Then you want to find maybe a product range or a person. How much weight do you put into that skillset in that first hire?

• 1:03:23Speaker 00

  I actually think it's less about expertise in skillset, if that makes sense, and more their ability to, again, I think of it like a portfolio manager. So this is more on the growth marketing side and bringing in acquisition. They are managing like a portfolio and they're trying to figure out what works. I actually think you need to find someone that's analytical for this role, but that also understands things like who is the user. They're like really creative and finding the user. And so it's actually looking for attributes, but not expertise. I actually think the more expertise someone has, the more. It actually can lead to like a false precision and thinking they know what they're gonna do.

• 1:04:08Speaker 00

  And especially like, I don't think you actually need paid marketing expertise till much later. When you're starting to think about incrementality or you have like different, you know, you're managing all these campaigns. Like, I actually think the expertise is more important later. And then similarly on product growth, I actually think product growth is like not higher till much later. A lot of early stage companies don't even have a product manager till later. And so I find that like a growth product person isn't till much down the road, but later down the road.

• 1:04:36Lenny Rachitsky?

  Just a couple more questions. One is you mentioned that it sometimes makes sense to bring on an advisor. I know sometimes companies have a bad time with advisors that just don't provide much value and they're giving them equity. Other times it's transformative, some of the stories you've shared. When is it appropriate to hire an advisor? And there's any, I guess, advice for what to look for in a growth advisor at this early stage especially?

• 1:05:00Speaker 00

  I would add an advisor if there is a probably like a knowledge gap on the team. And I would say, and advisors come in so many different forms too, and everyone does it slightly differently. Right? You know, for some folks, it's a month a call. For other times, like I, especially when I'm full time advising, I'll have like weekly calls. I'll even join some team meetings. I'll look at mocks and so everyone does it slightly differently. And so I think it depends on what you're looking for. I would definitely say that even getting to know the individual and making sure you're on the same page on what you're looking for and what the goals are. And then what I've done in the past too is initially set up like a shorter engagement, like a quarter long engagement.

• 1:05:44Speaker 00

  And then decide if you want to go longer. And I also think it's fine to, you know, let's say you have an advisor agreement. You're not getting value to basically part ways if it's not, you're not finding value. I think every advisor wants to make sure they're adding value. So I definitely think it's like, you know, to summarize, being really explicit on what advice you're looking for and making sure you're on the same page of what, what you want. And then also set up a try before you buy. If you want to do like a quarter long engagement first and knowing you can always part ways if it's not a fit even before that. Period of time.

• 1:06:20Lenny Rachitsky?

  Last question before we get to our very exciting lightning round. You've brought up this concept of first principles thinking. I'm curious what you, how you measure that and how you get a sense of is this person's strong at first principles thinking?

• 1:06:34Speaker 00

  It's definitely a word I use a lot. First principles thinking, I think of it as you are not using a set framework and set formula, but you're creating your own based on the context that you're getting. And so when I think about first principles thinking, often it is knowing what questions to ask so that you can start forming a mental model. And then it is actually starting to form that mental model and then knowing to evolve it and knowing when it's not working. And really coming from a place of curiosity of like, is this really working? This is something that I'm known for in my team as well, which is I ask tons of questions, but it doesn't come from a place of wanting to show that I'm asking good questions or

• 1:07:19Speaker 00

  anything that comes from a place of trying to solve the problem and making sure that we're always solving the problem at hand, making sure we're doing the right things. If there's new information, do we actually still want to do it this way? And so I think first principles thinking is often about like asking questions and then creating your own framework. That's how, that's how I would define it. And it's maybe another way to describe it is critical thinking. It's like you're able to think very critically. And I think it's important to, at least for me, create a culture where that's okay. Right? I think the moment you have a culture where people aren't asking questions, aren't constantly revisiting their work, that's when you know, you're not, yeah, maybe do like pushing yourself to do your best work. And I think it also just creates a fun environment where we're like, oh yeah, why are we doing this?

• 1:08:03Speaker 00

  And really leading with your curiosity.

• 1:08:06Lenny Rachitsky?

  Is there an example of a person or moment or a question that comes to mind of like, this is an epitome of a first principles thinker moment or question or way of approaching something?

• 1:08:17Speaker 00

  My aha moment of the value of first principles thinking was when I was at Dropbox. And we had the most unconventional people on our initial sales team. Dropbox was known for this. We would hire a ton of like really smart people that had never done sales and had them do sales. There are a lot of disadvantages to that, I think. Like we were figuring a lot of things out, like maybe we should have split, like had a few people that knew sales better and like a combo of both. But I do think it led to a ton of innovation. Like even I actually started on the sales team. I used to, this is a fun fact, I used to answer the 1-800 number at Dropbox. And if you go to Dropbox's website, you see a chat bubble. I used to also do that role. And so I think that what we got from that was just, that's how we got our very innovative

• 1:09:02Speaker 00

  go-to-market motions that also gave a ton of people, because a lot of those people then moved into different functions at the company. They had all this context on who the user was. They had talked to so many different users at that point. And that's actually what helped me a lot when I moved into growth is I had all that context. And I learned from that, going back to first principles thinking, that if you take people that are just super smart, they've never done it before. One advantage of that is they can innovate because they also, I think they come in with like, I don't know anything, let me just like figure this out versus someone that might know, think they know all the answers, limits you into what you are going to do. And so my aha moment was really at Dropbox, seeing so many times people that had never

• 1:09:45Speaker 00

  done these things and then seeing so much innovation come as a result of that.

• 1:09:51Lenny Rachitsky?

  That is an awesome story. Is there anything else you wanted to share or touch on before we get to our very exciting lightning round?

• 1:09:57Speaker 00

  I think that's it. I wanted to make sure, I know I talked a lot about, you know, developing people. So thank all the people that have helped develop me in my career. And then especially thank all the folks that I've worked with in my team, especially the team at Webflow. And particularly wanted to make sure to thank Shing Lin, Rory Davidson, and Joe Wang, who joined me from previous companies to Webflow.

• 1:10:19Lenny Rachitsky?

  Shout outs. Well, with that, Melissa, we have reached our very exciting lightning round. I've got six questions for you. Are you ready?

• 1:10:27Speaker 00

  Yes.

• 1:10:28Lenny Rachitsky?

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

• 1:10:31Speaker 00

  The first one is Leaders Eat Last. I really like that leadership book. Um, I assign him Simon Sinek. I also two non-career related books is The Untethered Soul. It really has taught me a lot about being present. And then also The Four Agreements, which is like a very short and easy read, but good principles to live by.

• 1:10:52Lenny Rachitsky?

  What is a favorite recent movie or TV show?

• 1:10:55Speaker 00

  This one isn't super recent, but Winning Time on HBO. It's about the L.A. Lakers during the eighties and the Showtime era. I'm originally from L.A. and grew up a Lakers fan. So it's it's a fun watch for me and a nice escape.

• 1:11:09Lenny Rachitsky?

  You will love a new movie I just watched last night called Air, which is about how Nike got Michael Jordan signed and it's similar vibes to that show.

• 1:11:18Speaker 00

  Yes, yes. I actually just watched that recently too.

• 1:11:20Lenny Rachitsky?

  Okay, okay.

• 1:11:20Speaker 00

  That's good too. Yeah, I've watched all those basketball.

• 1:11:23Lenny Rachitsky?

  Oh, man. I also grew up in L.A. Also a huge Laker fan from

• 1:11:26Speaker 00

  Ah, nice.

• 1:11:27Lenny Rachitsky?

  From before. Next question, what's a favorite interview question you like to ask?

• 1:11:32Speaker 00

  For me, it's not a question, but it's that that stage of preparing before the presentation and, you know, getting a sense for what it's like to work with each other. I think that has been one of the best ways for me to get signal.

• 1:11:44Lenny Rachitsky?

  Can you say more on that?

• 1:11:46Speaker 00

  Yes. So it's essentially that prep call before I ask them to do a presentation and going through the presentation together. Yeah. And working together on on refining it.

• 1:11:57Lenny Rachitsky?

  Awesome. We already talked about that, so I'll move on. What is a favorite product you've recently discovered that you love?

• 1:12:04Speaker 00

  I feel like everyone's saying this, but ChatGPT. I feel like it has really changed everything. There are so many interesting ways to use it. My team at Webflow right now is also starting to think about incorporating AI into the product. And so, yeah, I just think that is a Yeah, so many, so many things you can do with it.

• 1:12:22Lenny Rachitsky?

  What is something relatively minor that you've changed in your product development process that has had a big impact on the way that your team executes?

• 1:12:30Speaker 00

  This one here is what I also spoke about for earlier, which is, I mean, thinking through your, your DACE. It sounds so simple, but I do think a lot of times teams are thinking through how do they work with other teams, who is driving, who is the decision maker? And so having a DACE I have found is, is really helpful.

• 1:12:51Lenny Rachitsky?

  Final question, you've been at Webflow for a number of years. What is a favorite pro tip for using Webflow?

• 1:12:57Speaker 00

  I actually have two, if that's okay.

• 1:12:59Lenny Rachitsky?

  Even better.

• 1:13:00Speaker 00

  Yeah, yeah. Yeah, yeah. So one is, you know, one thing that I I've often heard from folks is it's hard to learn Webflow. And so basically watching our university videos, which is where we teach Webflow while also building in the designer. And we actually now enabled to have the videos, you know, in the product. So you can do them side by side. And then the other one is our Figma to Webflow plugin, which is you can take a Figma design and then convert it to Webflow, which is a great hack if you already have a design in Figma.

• 1:13:32Lenny Rachitsky?

  Wow, I did not know that existed. That is a really smart idea and feature. Melissa, I could see why people follow you from company to company. I feel like the companies that are going to get to work with you in this new stage of your life are also very lucky. Thank you for being here. Two final questions. Where can folks find you online if they want to reach out? And how can listeners be useful to you?

• 1:13:50Speaker 00

  Folks can find me on LinkedIn, also on Twitter, Melissa M. Tan. And then how can listeners be helpful to me? I mean, I, I love jamming on things, growth, thinking about leadership and managing. So if any of this resonates, you know, reach out, I'd love to have a discussion. And yeah.

• 1:14:08Lenny Rachitsky?

  Amazing. Melissa, again, thank you for being here.

• 1:14:11Speaker 00

  Yes. Thanks so much, Lenny. This was fun.

• 1:14:14Lenny Rachitsky?

  Bye, everyone.

• 1:14:17Lenny Rachitsky?

  Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.