Lenny's Podcast: Product | Growth | Career: Building high-performing teams | Melissa Tan (Webflow, Dropbox, Canva)

My aha moment of the value of first principles thinking was when I was at Dropbox, we would hire

a ton of 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, 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. If you take people that are just

super smart, they've never done it before. One advantage of that is they can innovate,

because I think they come in with, I don't know anything. Let me just figure this out.

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 long-time 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 Rowe, 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. If you're looking for help with go-to-market plans,

growth strategy, building your growth team, lining your sales, marketing, and growth efforts,

she's about to become available, so definitely reach out. 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

like Canva, Grammarly, Miro, Rowe, 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. 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.

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Mixpanel.com slash Friends slash Lenny. And while you're at it, they're also hiring. So check it

out at Mixpanel.com slash Friends slash Lenny. Melissa, welcome to the podcast. Thanks, Lenny.

It's great to be here. I'm excited to have you on. I hear there's a big development in your career

that is going to 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.

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, 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. Amazing. That's a huge news because

there's a small number of people like Melissa that is available at certain times to work with.

And this is going to be this window. And I just want people to understand what kinds of areas

do you think you're going to focus on for folks that may need help and may want to reach out?

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, and retention. I've also advised and helped growth teams. So kind of across stages,

focus on growth and go-to-market. I guess while we're on it, what's the best

way to reach out? As people are listening to this and like, oh my god, I want to get some help on

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

Great. So usually we cut that cover at the end, but I think that was going to be helpful in case

people were 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?

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

So before we get into it too deeply, I want to first talk about Dropbox. So you're Dropbox for

four-ish years, something like that, doing a lot of their growth work. And it was in the middle 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 work,

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. 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? 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 1500 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.

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 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, etc.

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're 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 is in the details and

the devil is in how you execute. 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? 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 in 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. 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 been really intentional

as we thought of the collaboration across product and growth. So that was definitely a learning.

So I guess the four things there are just the 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? So you said Dropbox. Essentially, there was a late investment in

sales. And there's a sense maybe product like growth is going to take us really far. And like,

I imagine like, look at Jira and Atlassian. 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 like product that is working? 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 as 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 is, you know, 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.

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 surface. 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 just more conducive to an enterprise and sales motion. 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

and what the paths and journeys look like, it just ends up being more seamless to the user.

And, you know, yeah. 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,

Metaford, from other people is that you have this reputation for being a person that

people follow from company to company, which is like the ultimate sign 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?

I've been really fortunate. 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 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 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 how I would describe that.

Some people may be hearing that and feel like there's this choice you have to make as a leader.

Do you really 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 achieve and drive impact while also

feeling like you really care about them? I don't think that they are mutually exclusive.

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 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. What's an example of caring deeply about

someone and being that kind of leader? People may be listening and are like, yeah, I care a lot

about my reports. But what are some examples of what that means to you that maybe would surprise

people? 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, etc, 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 they were in the right path,

we just need to get there as quickly as we can. And so I gave them that feedback. And afterwards,

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 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 would give that feedback is because, you know, they can do

things differently, and you just want to help support them. 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 them, you're giving them 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? 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 to 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 pulling 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 own help as well. Those, I think, are the things that go along well. And

I think the third thing is, as you give someone 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 a different way. And so keeping the feedback really about the work itself

and the specific things that you think can be improved.

I know you're also a big fan of developing talent internally versus hiring experts from the outside.

It's always this decision, I think, as a leader and as a company. 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 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? 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 and getting 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 to that really stand out

are from Dropbox, Oliver J goes by OJ, and GC, Leonenni. So it really has come from a very

personal place for me. Secondly, I think it 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 and 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 sense from just

like de-risking the situation as you're scaling. 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. It 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 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? 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 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 success

will be tied to their success. This is actually what happened. I mean, it's not like you need to

be super strategic about that. But 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 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.

Any tips on the questions maybe to ask a manager to help them 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?

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,

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 Cheryl

Sandberg wrote this in her book, Lee Ninh, 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. 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 you want to set up some type of monthly

thing, I think you want to 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.

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 going

to, if they have the time, they'll say yes. Tim Ferriss talks about that too. He's like,

never ask someone to be your mentor. As you said, it's a scary proposition. You're committing to

something. It's pressure versus just like, hey, can we just meet? And can I just get some advice?

And then maybe after you do that, can we meet next month also and just kind of help it grow

organically? Yeah, definitely. 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,

can you just list the companies you work with, some of the companies you've worked with?

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. 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? 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 AR,

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.

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 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. And that's like how we are ultimately measures the

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. 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 here 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 think that it's easy at work to, especially in high-pressure

environments, easy to get stressed and all that stuff. And at the end of the day, I think the

more fun, this is very personal to me, but the more fun you can have, the better everything is.

And so just making sure you're infusing fun along the way and you're not taking things too seriously.

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 not 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.

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

I think it first starts with defining the scope that everyone is going to own and drive, right?

So as you are sitting at 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. And so that's quite a lot of impact

and being a finance team, they said logically, we should just double the team. If each person

brings it in more than a million, we want to double the ARR, let's just double the team.

And so I actually pushed back significantly, though I thought to myself, 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 going to help us recruit people that

were excited to solve such small parts of the growth problem. And so really thinking about how

do you carve out scope? And 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, etc.

So first starting out with carving out good scope. And then the second thing is just infusing a

culture of thinking like an owner. And this infusing of the culture, I think it comes out

in a few ways. One is, and this is really common 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 design or engineering.

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

can do? And did I exhaust all the options? And then finally, 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. And finally, 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.

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 throw them under the bus or anything, but I feel like

everyone I know at meta, their performance review is very tied to their impact. It's very

impact driven. And that leads to people needing to drive impact themselves. I drove this impact

and they look at 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 I need

to do this myself? 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 feel 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. 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 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. 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. And so I also showed my team, hey, I'm also doing all these things to

help the company. And I think that is what helps set that tone and that culture.

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?

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.

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 focused. 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 taking on too much.

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that's getepo.com and 10X year 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 have you seen works. In terms of developing talent, I think of this as like stages

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 their role, it's a good mutual fit.

I also tend to look for folks that have a growth mindset. They're 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, the company? 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 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 journey here. Here are some things where there's low hanging

fruit or even rotting fruit that you should take on into 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. It's hard to sometimes get visibility and get live meeting calendars,

but if you create a five or 10 minute loom on something you did, that's just a great way to

get visibility. 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, 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 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. 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. Yeah, definitely. Interestingly enough, Kim Scott was at Dropbox

for a short period of time. So when I joined Dropbox, she was actually on my interview panel,

and we overlapped for three months. And she actually workshopped that book with our team

before she published it. And that always resonated with me. And I remember her saying,

you have to, I forget the exact words, but it's essentially like be direct, but deeply care.

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

Yeah, care deeply, but challenged directly. And that has always been something that is

something I try to infuse and has really inspired me as a leader.

We're going to 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 a performing team. 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? 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 going to say anything groundbreaking here, but 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.

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 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 it's the biggest

signal to what it's going to be like to work with this person.

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 it?

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 solving. 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, would 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. And

depending on what you're hiring for, we just have each person focus on a different competency. And

it also depends on the roles. 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 wanted that like

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. Before that, we have that preparation call with me where often candidates will have

questions like, oh, 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. And sometimes I've seen candidates that didn't

incorporate any of it. And I kind of am like, okay, this is like, probably not a fit. And it

actually, I think the 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 think, I guess,

lastly, it gives them a taste of what it's like to work with me. 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. Maybe two very

logistical questions there. How much time do you give them to work on this presentation?

And then two, you said that you asked some questions related to the actual problem they're

solving versus a theoretical problem. So those are two questions, I guess.

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, don't exceed more than X number of slides.

In Webflow's case, we've done don't exceed more than 30 slides. And that's 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.

And so that's how much time we give them. And it's usually a 30-minute presentation

with 15-minute Q&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 four minutes 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? 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 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.

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.

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 Abhi Kuzmanoff,

who was on my team at Dropbox, about this because I felt like even at Dropbox,

it's a great thing. We were haphazardly finding amazing things. We had a freemium consumer product,

then we realized people wanted a team's product, so we built a team's product,

but we never created that whole blueprint of what should it look like and what are the different

connection points across consumer business, 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, 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,

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 an important thing. My 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. Folks 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 and conversion makes a difference. But if you're early stage,

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. 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

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 infuse in the company. 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, on the reverse, thinking about as PMs, how can PMs be more growth oriented as well?

I like the term flying formation. I've never heard of this before. What is that exactly?

Again, is that just how growth is integrated within the company?

Yeah, I guess flying formation, essentially, I don't know where it comes from. I guess it's

maybe it's a military term or something. I can say that. Yeah, like the Blue Angels.

Yeah, yeah. I think of flying formation as like, how do we work together across teams?

You also can think of it as like a daisy too, like driver accountable, contributed informed.

I think sometimes when you don't know how you're going to work together,

you end up stepping over each other's toes. You're unclear who was 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 daisy of like, what are the different roles?

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

A daisy 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. 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 daisy. 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're 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,

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 and their 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's some projects that we

might also work on together. And so it's essentially that meeting cadence that you're going to have,

the operating rhythms. That's essentially how I think about a flying formation.

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.

Yeah. 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?

Really, it 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 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 signups and customers efficiently.

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.

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?

I get this question a lot as well. I'd say initially, when a company's 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 in 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 is in someone driving acquisition.

You need to find your first 1,000 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 ideally they understand maybe one or two channels well,

and 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 many channels that are evenly. It's they find one or two

that really work and make up like it's 80 20 rule that 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, there are a lot of agencies out there for SEO for

paid marketing, etc. 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

that role 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

our 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 on board onto

the product and have them talk out loud, you'll fight a lot. And you can also just take best

practices of like onboarding checklist, etc. 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. What kind of profile have you found to be most successful for this sort of person?

Some people will look for like a, I want to hire a Melissa and like, let's just go go big,

the best person I can find to have them own this versus someone that just

knew from school that's going to figure it out. And I guess they're somewhere in the middle.

What do you find is best for that first hire? 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 an acquisition before,

maybe they're a little bit earlier in their career. 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 every forage 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 can 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. And so it really depends on the

context who's also on the current team and who you want to bring into. Are you looking for

an actual leader that's going to scale with the company or are you not ready quite yet for that?

What about in terms of their skill set? 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 a 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 skill set in that first hire?

I actually think it's less about expertise in skill set, 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 then thinking

they know what they're going to do. 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. 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 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?

I would add an advisor if there is a probably like a knowledge gap on the team, as I would say, and

their advisors come in so many different forms too. And everyone does it slightly differently,

right? You know, for some folks, it's a monthly 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 two is initially set up like a shorter engagement, like a quarter-long

engagement, 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 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 know as part ways if it's not a fit even before that period of time.

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 strong at first principles thinking? 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 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're not maybe 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 and really leading with your curiosity?

Is there an example of a person or moment or question that comes to mind of like, this is an

epitome of a first principles, thinker moment or question or way of approaching something?

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 like 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 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 Principal's thinking that 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 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

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

That was an awesome story. Is there anything else you wanted to share or touch on before we get to

our very exciting lightning round? 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 Shinglin, Rory Davidson, and Anja Wang who

joined me from previous companies to Webflow. Shout outs. Well, with that, Melissa, we have

reached our very exciting lightning round. I've got six questions for you. Are you ready?

Yes.

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

The first one is Leaders Eat Last. I really like that leadership book. I signed 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 a good

principle to live by. What is a favorite recent movie or TV show?

This one isn't super recent, but Winning Time on HBO. It's about the L.A. Lakers during the 80s

and the Showtime era. I'm originally from L.A. and grew up a Lakers fan, so it's a fun watch for

me and a nice escape. 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.

Yes, yes. I actually just watched that recently, too. That's a good one, too.

Yeah, I've watched all those basketball. I also grew up in L.A. and also a huge Laker fan.

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

For me, it's not a question, but it's that stage of preparing before the presentation and 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. Can you say more on that? Yes, so it's essentially that prep call before

I ask them to do a presentation and going through the presentation together and working together

on refining it. Awesome. We already talked about that, so we'll move on. What is a favorite product

you've recently discovered that you love? I feel like everyone's saying this, but chat,

GBT. 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 I just think that is so many things you can do with it.

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?

This one here is what I also spoke about earlier, which is, I mean, thinking through your

daisy. 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 daisy

I have found is really helpful. Final question. You've been at Webflow for a number of years.

What is a favorite pro tip for using Webflow? I actually have two, if that's okay.

Yeah, yeah. So one thing that 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. We actually now enable to have the videos in the product, so you can do them side

by side. The other one is our Figma to Webflow plug-in, 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.

Wow, I didn't 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. Working folks finding online if they want to reach up, and

how can listeners be useful to you? Folks can find me on LinkedIn, also on Twitter, Melissa M. Tan,

and then how can listeners be helpful to me? I love jamming on things, growth, thinking about

leadership and managing, so if any of this resonates, reach out. I'd love to have a discussion

and yeah. Amazing. Melissa, again, thank you for being here. Yes, thanks so much, Lenny. This was

fun. Bye everyone. 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 Lenny's Podcasts.com. See you in the next episode.

Machine-generated transcript that may contain inaccuracies.