Stage of company: a career unlock

Nikhyl: Hi everyone. Welcome to another episode of the skip podcast, the podcast dedicated to advancing your tech career. I'm your host, Nikhyl Singhal. And today's episode focuses on stage of company. About four years ago, I wrote an article on Substack, it was actually my first article I pulled together this concept that people ignore stage of company more than they should and focus more on name of company.

I think people are like, Oh, should I join Google or should I join Rippling or should I join Notion or should I join the startup or my buddy or should I found. And what I suggested is forget the brand names, forget your buddies, think about the stage of company that's right for you.

And more importantly, I observed that product management specifically as a function, and though I think it can apply to marketing as well, these glue functions transform themselves every time a company goes through growth. Though you might be a product manager at an established company, moving to a small company might be a complete shell shock because product management is performed vastly differently.

So today's episode is really around demystifying this whole area around stage of company, product management, and how growth phases actually impact the function. My hope is that by the end, for most of you, especially those that are product managers, you'll find a stage of company that is most connected to where you want to go in your career.

And it might actually be exactly the company phase that you're at today, or it might be vastly different. And if you're starting a job search, it'll help you try to understand where you should focus and where you shouldn't.

And the format of today's episode is a format that I've been experimenting with the last few episodes. It's a Q & A style model where I take questions that are emblematic of the questions that I get when I'm coaching folks, I generate the voices and the narrative using AI. And then we go back and forth as a way to explain the concept.

There's a bunch of pieces here, and I think this is a more effective way. To get the information across. always looking for feedback on the format itself, but why don't we just get started? We'll start with three different characters that are coming to me with questions around career. And ultimately we're going to talk about stage of company as the answer to those questions.

Catherine: Yeah. So I'm feeling a bit overwhelmed with my job search at the moment. Like, you know, there's just so many tech companies and positions out there. Most of which I've never even heard of before. So yeah, it's challenging to find a job with all this, you know, it feels like option paralysis and I need to seriously narrow things down somehow and to focus a bit.

I'm just not sure how. The thing is, Digging a little bit deeper here. Most of the stuff I actually care about. It's not something you can figure out from a job listing. I'm talking about like who your manager is going to be, what the culture is like, what kind of project you'll be working on, that sort of thing.

So I'm wondering, how do I even begin to approach this? What's the best way to get started and make this process more manageable?

Jack: here's the thing. Work has been getting increasingly frustrating for me. Like, there's an underlying feeling that the company is just different now. I mean, I get it. When a company grows, they'll move slower, but it's more than that. All those things that got me excited about joining in the first place are now completely gone.

So I'm thinking, do I need to suck it up and deal with these changes? Or is this whole situation trying to tell me something? Like, maybe it's a sign for me to really get out there again and, you know, look for something new.

John: mean, I was super excited about this gig. Um, you know, coming in as the head of product, building up the team, really expanding our product line, it all sounded great on paper. The thing is though, and once I hit the ground running and really looked under the hood, I realized our flagship product isn't quite the superstar they made it out to be.

So, now I'm kind of worried that adding new products and bringing in more PMs might be jumping the gun a bit. I'm considering whether I need to refocus on strengthening our existing product before pursuing expansion. And to be honest, I'm also reflecting on whether joining this company was the right decision.

Yeah, it's a challenging situation. I'm not really sure what the best move is here.

Nikhyl: So as I signaled these questions, though, they're somewhat different from one another stay versus go versus how to start a job search all relate to stage of company. And I think there's two key points that I want to get across.

One is that companies themselves, though, you know, company and company B are going to operate pretty different. Maybe have different projects, different markets, different domains. What I've noticed is that companies that are in the same stage of life often have very, very similar problems. And we're going to go through what those problems are in a second.

And so you might say, Hey, I'm not happy about my seed company or my series B company, and I'm going to go to another series B company. But what you'll find is that most of the challenges are going to look at least at the 10, 000 foot level, quite similar to one another. So if you think about it that way, then you actually start to realize like, Ooh, stage of company is the first question I should be asking, because that fixes the set of problems that I'll be dealing with.

The second thing is more related to product management. And as I mentioned, product management tends to change as the company grows and matures. many of you might find that sort of obvious, but if you think about it, that's not actually how most people talk about product management.

They talk about product management, kind of like capital P capital M it's a fixed thing. But what we'll find is that product management in a startup or in a company that's still struggling for product market fit. It's going to be vastly different than a company that has a market leader. And that's not the way sales and engineering, in my opinion, operate.

If you are hands on building something, the idea of software development doesn't vastly change as the company and the product scales. Similarly, core selling skills remain the same, but I'd argue that for marketing and product management, these functions that kind of connect building and selling together.

It does change in a fundamental way and what that entails is that if you're excellent at a product management at one phase, you might really struggle in a different phase. That's why this topic is so important that companies tend to have similar style of problems and the function of product management will transform itself as you go through growth.

Catherine: Can you break down what you mean by stage of company a bit more? Like, is it just about how big the company is or is there more to it?

Nikhyl: Yeah. Size of company isn't really the signal that you're looking for, though. It's, it's connected. Sure. The size of revenue that a company has and the number of employees. has a lot to do with stage. But when I think of stage, I want you to think about this sort of S curve of growth. And so for those of you that aren't familiar with it, we're going to draw it in your mind.

So imagine taking an S and putting it on its side. So it starts out flat. And then all of a sudden you see it start to grow at an exponential rate, and then when it hits this inflection point, it starts to flatten out. So it's sort of a flat side of an S, then an arc, and then another flat side of an S.

And that's kind of the growth that we see in companies that, you know, maybe a better way to describe it as phase one is a almost a drunken walk. Where you're going one direction for a little bit, and you go and change dramatically to a different direction as you're learning about customers. So you're in this mode where you're almost like this squiggly line where you're rapidly experimenting, trying to find something that works.

That's kind of your phase one. And so that's the very beginning of this S curve. Now, if you're lucky and most companies don't get there, quite frankly, But if the founding team, if the early stage team manages to find something that's working, meaning that the customers are really starting to like what's being built and we start to see some set of repeatability.

Then we start to see those lines and those squiggles start to calm down and you start to see a growth in its valuation and you start to see more value accreted to the product.

Customers seem to want what we build. It's almost the sucking sound that the business is experiencing. So if you are starting to put something out there, you don't have to tell a lot of folks about it. You don't have to spend on marketing and your sales people aren't pounding on 50 different doors to get a customer.

You start to see people say, Hey, that product is really important to me and I need it. And if product went away, there would be a lot of pain for that user, that customer. You're starting to see real product market fit. If you have a customer and you build something and then you get a second customer and you're effectively building something almost different for them and then you have a third customer and you have to do a third variant of the same thing, you may have three customers.

You may have revenue, but you don't really have product market fit. And if you keep hiring in order to satisfy all this demand, that means you haven't quite gotten scale. But if it turns out the first product meets most of the needs of the second and all of the needs of the third, you're really starting to get some nice velocity when it comes to efficiently building your product and selling it, and that's the sucking sound I'm referring to.

So pre- product market fit is when it doesn't exist at all. Post product market fit was when you're starting to protect it and you're seeing it, and you've gotten from those first few customers to something that's repeatable. And of late, say over the last 10 years, at some point you might see an exponential rise.

We call that the hyper growth phase, phase three, hyper growth. And when you see this exponential rise, what you're seeing is you almost can't satisfy demand. The line outside the restaurant goes down the block. And what you have is not only something that doesn't have to change to satisfy each customer, but you have this sort of amazing amount of demand at a very efficient cost.

And the reason why this is happening of late, maybe a last decade is because it's a lot more efficient to sell things with app stores, with Google ads, with Facebook ads, the efficiency of reaching customers has gone up to such an extreme level.

That you can actually effectively turn the crank digitally on distribution. And that's what leads companies to see amazing growth. You know, the example of Uber in 18 months, getting the same scale as LinkedIn took 10 years, both amazing and successful products. People are able to see a car, take out their phone, download the app, sign up and actually call a car within 60 seconds. That's an amazing innovation. And that leads to these hyper growth phases. Naturally hyper growth is rather rare and in fact is more rare these days than ever before, has a lot of these hyper growth companies that existed were fueled by low interest rates and they were fueled by venture dollars.

Nowadays, you don't see as many of those companies, but clearly if you are a hyper growth company, you are doing something right. And if you continue to succeed, you become kind of the market leader and you reach that scaled level. That's just the fourth level. This is where we see all the big tech companies where they have market leading products, number one in the market, and they have established themselves.

So you've got these four phases, this pre product market fit, drunken walk, experiment, finding the first customers phase. Then you've got things are starting to work, and now you're starting to refine that product and drive efficiency in the hope of making the sales so cheap that you end up hitting this hyper growth phase where now you're in that arc of the S.

And then finally, if you're lucky enough to have that success and to have that global product or have those customer wins, you can become that market leader and you can be at that next level where you tend not to see as much growth on that product because the market's sort of saturated and that's why it flattens out a bit.

Catherine: So that's how you're slicing up the company stages, and you're saying product management isn't just one job description, it sort of shifts as the company gets bigger. So, what's a product manager actually doing in one of those early stage or seed stage startups?

Nikhyl: Yeah. So we're at this drunken walk phase of company. And this is one of the more interesting phases for a product manager because the founders are so heavily involved in finding the product that customers are going to want. I sometimes describe it as, you know, everyone's rubbing two sticks together, hoping to find smoke. so if product management exists at this phase, it's going to be a very hands on function. It's going to be deeply connected to the founders. Execution is going to be the biggest objective function. In fact, speed of execution, clarity of understanding the data, clarity of working closely with the customers and the sales team, the engineering team, and this obsession with doing more of things that work and less of things that don't, so it's extremely scrappy.

So you might be thinking, well, isn't that the definition of product management? And I'd say it is to some extent, this is a extremely rapid level of experimentation, but we have the opposite when it comes to process. We're in fact, allergic to process at this phase. We aren't interested in building out a large product team.

We aren't thinking about organization and we're not even thinking about building a second product. Well, we are focused all hands on making one thing work with the first set of customers.

Catherine: you know, I really like that you called out what's not required. I mean, it really helps me understand like why product management is so different at those more mature stages. Um, so I guess, yeah, my next question would be, what actually happens, you know, when we start to see some real customer traction?

Catherine: So in this case, we've been rubbing sticks together and we now see smoke. And our goal is to ensure that the smoke turns into fire and doesn't go out. So now product management goes through its first transformation because the rapid experimentation throw things away. Now is actually a non goal.

Now what we want to do is stay the course. We want to protect what's working and make it more predictable.

So for the first time, you're starting to hear things like prioritization, roadmaps, structure. We're saying no more than we're saying yes. We're also thinking through how to build the organization just a tiny bit. And what I mean, the organization, I don't mean the product management organization, I mean, the team as a whole.

Now we have probably multiple engineering teams, which don't always know what everyone's doing. So we need to make sure there's a basic degree of communication on what we're prioritizing. We're starting to put maybe the first semblance of a platform together. everything that we're building is not designed to throw away, but it needs to be now stable.

It needs to be higher quality. the sales team needs to have something predictable so that they can sell it to the next customer, not something different every time they go out to the field

and product management is now heavily involved in working with all the different executives to make sure that everybody is on the same page. And we, in fact, might be hiring our first couple of PMs. So just contrast that. With what we suggested in the earlier phase, and you start to see my thesis as to why product management has shifted so dramatically.

Now, we're still not looking to build a second product. We're still pretty careful on introducing process that's lightweight. We don't want heavy process, multiple layers of management, we do need more than we've seen in the first phase.

I think all of you can see how different it is from the leader or the product managers that are attracted to the first phase, because the first phase is super entrepreneurial, this is a lot more of what people think about with product management, communication, prioritization, structure, process, predictability.

These are the things that product management provide. But again, there's a huge difference between where the company is from a product market perspective.

It sounds like these lists are practically opposites of each other.

It's like night and day between the experimental phase and when things start working. So, does this pattern continue? Does product management keep shifting as the company scales?

Nikhyl: So in some ways, hyper growth might be the most fun of all of the different phases. And as I mentioned, there are. fake hyper growth companies that have existed over the last decade, because there's a lot of companies that actually don't have product market fit, but that are scaling really rapidly.

And the reason why is they have some early traction and then they're using these dollars and they're inefficiently going after these next set of customers, or perhaps they aren't able to make more money on a per customer basis, but they're sort of assuming that they'll eventually get there if they just build their way out of it.

And so they're in this land grab mode. And those companies are really struggling. They're actually more X growth companies than growth companies. But in general, if you find companies that are scaling where they're able to do so super efficiently, when it comes to customers, there's almost like this sucking sound for their product.

That's one of the most fun places for any employee to be because you've clearly got something working and product management becomes like all things to everyone in one shot. Because what you need to be able to do is now scale the core product on a next level basis. Here, you're not just trying to protect your creation.

Here, you're trying to become market leader, and you've got plenty of users that are coming in for the product you have. But there's obviously going to be now competitors. As people are noticing, you've got something working. So you're feverishly working on scaling the product and the company needs to scale itself as well.

So the level of prioritization, the level of process. The quality of the roadmap, the quality of the communication and the importance of making sure people are building things durably goes up almost instantly. Lot of your deep product management core skills becomes important, but the company is also in a position where they're really ahead of the curve.

They're seeing so much demand that there's going to be anxiety and excitement around innovating, building the second product, building the third product. And many of these hyper growth companies are essentially saying, look, I've got something working. Clearly, I need to scale it and make sure it doesn't fall over.

But I want to take advantage of that first product. Shepherd them into a second product and then shepherd them into a third product, because you've got this moment where you're able to invest. And certainly there's lots of dollars now available, especially these days, as there are rather few companies that are in this phase.

When they're so successful, lots of people are willing to shove dollars in because they know those dollars could really lead to a huge, huge set of product offerings.

So you might ask, what parts of product management doesn't exist at this phase. And I'd say that because you're innovating in certain areas of the company and you're scaling and others, you're actually taking some of the product management playbooks from the first and the second phase and using them both in practice.

But there is a boldness that comes in at this phase that's somewhat absent in the first two phases. And the first two phases, you're really trying to stay as deeply scrappy as possible and protect what's working or ensure you're throwing away what's not and finding the right product features for your early set of customers.

Here, you start doing things like acquire companies. Hiring ahead of demand, knowing that by the time you need to bring in people, it'll be too late.

So you end up creating a much bolder environment. You also have deep cultural challenges at this phase because you've got employees who have perhaps navigated your first phase. Succeeded in the second phase, and now they're being asked to do something radically different yet again, it's not so much as taking some time with a small scrappy team and finding product. It's very quickly in three months, six months, launching a new product on top of an existing customer base. It's not protecting something, but really ensuring there's roadmaps, there's proper planning, and you're bringing the whole organization into alignment.

So you can imagine the complexity of having product managers now that are able to innovate product managers that are able to scale, technical folks, able to build this sort of scalable platform that needs to sit underneath it, and then far more kind of strategy, business leading PMs who can look around the corner, think through what is the right product roadmap for the core product. What are the new products that one should develop, or perhaps even acquire.

It is all things going on. And this is one of the reasons why this phase was just so popular and continues to be so popular, but also very competitive to come in.

Catherine: Can you give me an example of how things might, like, change between the three phases we've already talked about?

Nikhyl: So consider planning for a moment, you know, in the early stage of the company, planning is kind of non existent. You're really hoping not to plan. You're really trying to just react. Second phase of the company planning kind of becomes important because now you have a team, a sales team, customer base, et cetera, that wants to know kind of what's coming.

The level of planning might be done relatively quickly because you don't have a ton of ability to change nor a lot of incentive to change the product. And what you're really doing is just very carefully protecting the asset and making sure it's durable, making sure it's reliable, making sure that it's predictable.

Now you're in this hyper growth phase. Hypergrowth is everything. It's essentially you're creating new products. And you're scaling as a result, your plan is almost like half of your team's time.

So no wonder when these growth companies come along, they hire a header product and they ask her how to product to put together the roadmap oftentimes for the first time. And oftentimes that exercise is very revealing because we just haven't needed one up until now and building a reliable product roadmap.

I mean, this is a hilarious conversation I tend to have with people is. Might take two months and they might do it every three months. So, so you feel like you're always in planning. I know a lot of you are nodding your heads right now, listening to this podcast. And that's because planning is a big chunk of time when you have resources that are going on various parts of the S curve all at the same time.

So planning is super, super critical, but it's dramatically more complex and a dramatically larger investment than any of the previous phases. That's why these phases are so different. And again, you can imagine a p roduct manager that maybe it's very strong at planning. Those first two phases are not actually a good use of that person's time.

But in this case, it might be exactly what we need. Hey, I can build a plan and I can establish it and change the culture to adhere to this plan. Well, that's exactly what this phase needs. So that's why I describe these phases so carefully.

Catherine: But there's one more phase. How's that one different from the others?

Nikhyl: yeah. So as I signaled earlier, if you're lucky as a hypergrowth company, you can become an established leader, like the Metas, the Amazons, the Oracles of the world. And these established leaders have a very different style of product management that accompanies their scaled products.

The biggest challenge that they face is ironically, the innovators dilemma. And for those of you that are not familiar with the term, the idea is that once you become established, you have a lot to protect and because you have a lot to protect, you move much more slowly and much more cautiously and because you move without boldness, slowly, cautiously, it's very hard to create something new because in order for something new to take hold, it has to have the same level of upside or promise that the scaled products have. Now, of course, as a startup, that's not at all what you're thinking. You're thinking about survival. Now, you're struggling with creating something new because you don't give it enough time.

You have the wrong process, et cetera, et cetera. So oftentimes companies struggle when they've become large and they've become successful with creating the next products. there's so much to protect and there's so much expectations on the success of the business, it's very, very hard to take risk, especially any risk that could impact the core product. This is, for example, one of the reasons why a lot of people are concerned around Google's core business. Google obviously has a lot to gain. By being market leaders in AI, but they also have a lot to lose because people won't go to their traditional core business of searching for things on the web because now they're looking for answers and those answers may not involve them clicking on ads or clicking on links.

And so there's an argument that they're going to struggle with innovators dilemma, though they have the ability to build the world class AI solution of the next 10 years. They may not want to, because of this challenge around atrophying its core business. This is typically what comes up in any company that's been very, very late stage and very, very successful.

So what does that mean for product management?

Well, I'll start by saying that there's a lot to protect, as I mentioned. And so most of the challenges around building new things become inside the building problems, not outside the building problems. We started to see a little bit of this creep up in the hyper growth phase.

As I alluded to the fact that now the organization's more complicated, you've built a product management team that's sizable and you've got different skills there and you've got different parts of the organization that need to be brought up to speed. You are spending a fair amount of time aligning folks and making sure that there's clear context as to what's being built.

But in this case, a small change to the product could have dramatic impact on the business. I saw this example play out at Meta where small changes in our ranking algorithm could have huge impact on the business, positive or negative, and a huge impact on the user experience.

And that ultimately is maybe a small line of code change. Which is crazy when you think about how powerful these systems are and how little change can institute such massive, massive amounts of impact. So what that means is there are 14 checks and balances that companies put in place, otherwise known as process, red tape, bureaucracy, layers of management, all to protect something.

Now, at the beginning of a company's phase, there isn't that much to protect. In fact, you're throwing stuff away almost every Tuesday because nothing's working. So the right answer is not to protect anything. Here it's the exact opposite. Here product management spends a lot of their time making sure that we don't make mistakes and we don't build the wrong thing, or we don't change the wrong thing in the product because there is a lot to protect.

Moreover, you are very motivated to continue to innovate in tech. It isn't interesting to just protect the core products. You really do want to create new and fight this innovators dilemma. what becomes the product management challenge is to protect this core product on an extreme level, continue to refine the product from a scale and process point of view, But also explore these adjacent areas and to to an invent a process that can enable product change to occur, even with an extremely large organization with multiple functions and multiple layers of hierarchy.

Ultimately, PM is the function oriented towards not only protecting the core product, but also changing it. And that machinery is really the deliverable of product management at this phase.

So like hypergrowth, there's going to be different flavors of product management, but I would say that those that tend to be more focused on outside the building problems, what does the customer want?

How do we build it? How do we get it out there as fast as possible? They tend to struggle. Because of the long lead times, because of the amount of red tape, bureaucracy, et cetera, those that tend to enjoy working across different functions, working at large scale are less worried about major rapid change in their products

but substitute that with working at scale with a product that's very well known and that is essentially established as a leader, those characteristics tend to appeal to this style of product manager.

Catherine: Okay, so I'm seeing like four different flavors of product management here, but how do I figure out which one's the right fit for me?

Nikhyl: Ultimately what I want you to do is ensure that your superpowers are on display for the phase of company that you're either in or that you desire to be in. So let's examine a few of these characteristics. So let's start with structure, now, let's say you're someone who thrives in structured environments. You like school. You did well in school. You like when people have clear rules that you can kind of understand and excel within. You look forward to things like promotion. You understand this sort of hierarchy. You want to be clear on expectations and you want them to be well defined going into a role or going into a project. Well, that's an example of someone who is a structured thinker and enjoys structured environments avoid those first few phases because structure sort of absent by default. In fact, it's a non goal as we've talked about, you know, if you join as product person in the early phases, they're not even going to know what product management is.

So you'll be asked to craft your own role, to set your own expectations. Now, some people really like that and actually don't do as well in structured environments. I happen to be one of them where as an entrepreneur, I thrived in situations where there was a really complicated problem to go solve, but the tactics weren't clear and the rules themselves weren't ones that I had to adhere to. So that's where you start to align yourself on which phase makes more sense early rather than late.

Now, team is another example. Let's say you like large number of people in your company that have the same function, maybe people above you, maybe people besides you, maybe even people below you. Well, again, the later stage environments are going to be far better than the earlier stage environments because simply there's smaller teams.

And you should ask yourself, do you thrive in larger or smaller teams? Do you thrive in situations where you have a boss or a manager who's in your same function? Now, most people would say, well, absolutely. Why wouldn't you want someone who's sort of your future self or that's been in your role? Well, you might not, you might want more of a leadership position where you're able to work with your peers who are in business and sales, go to market, marketing whatever it might be.

And in that example, you're not actually interested in a larger, more structured environment with lots of teammates.

Maybe the corollary is small schools versus large schools. And some people love small schools. Some people are large schools and there is no correct answer, but there's probably a clear answer for you.

So, as I mentioned, that last phase of company tends to be the latest stage companies, and they tend to have most of the problems are inside the building problems. some people love navigating the inside the building problem, which is navigating how to create and change the product when you have so many rules assigned to protect that product success.

Think about it as two deliverables for product management. You could be the type of product manager that likes building the car. And then you can be the type of product manager who likes building the factory that makes the car. These are two different products. But most of the time people find themselves more attracted to one versus the other.

Now on the surface, some people are like, well, why wouldn't you want to build a car? Isn't that being product oriented? But I'm not sure that's true. Lots of product managers I talked to, they don't talk product. They talk systems. They think about what is the system that needs to exist for a good product to come out the door. There are other people that have like 10, 15 apps on their phone. If they're consumer PMs they always have a point of view on what's wrong with this product.

What could this product do better? What are all the interesting products coming out and they're constantly tinkering with product. Those are car people. And my point is that in the first two phases of growth, you typically have most of the organization focusing on creating that car, but once the car's going, sure, a bunch of people are trying to make that car scale more, but that again, becomes more of a factory problem, not an invention problem.

And so even though there are zero to one innovation bets in larger companies and in these hyper growth companies, usually those roles go to folks that are very tenured. And frankly, the track record is quite weak on seeing success there. If you enjoy hands on building, if you're a product person, if you enjoy getting in the weeds, talking to the customer, really figuring out how to change it, You're going to be more comfortable in those early phases.

Catherine: So if I'm the entrepreneurial type and I love dreaming up products, then jumping into a product manager role at an early stage company sounds like it could be perfect, right?

Nikhyl: I'd be cautious because the role that you describe as being a hands on person at the beginning. Trying to build something sounds a lot like the founder. And the worst case scenario would be the founder brings you in as a product person, but then ultimately still owns and has responsibility for finding that product market fit, and you don't really have a position or worst case, they don't know how to do that.

You do have a position. You do have a need. But the economics around the risk that you're taking versus the reward are 10 times less than the founder. So you work really hard to build the right car. And then the founder takes all the advantages with terms of their equity and their level. You might as well found on your own.

In that case, So there's this caution around being in no man's land. If the company is relatively new, doesn't quite have product market fit, sees themselves as wanting to add product management, you should be really cautious. But if the company is starting to see some scale, being the first product person for a product that is working is substantially less risk than founding or coming in very early. Cause now you've got something that's working. You probably have financing. You're probably going to get a real salary, et cetera. And that's worth paying for particularly in this market when that equity, even if it's early is still large and those companies have quite a bit of upside because the market's pretty realistic on their expectations around growth and those higher quality companies are starting to get born right now.

But generally speaking, if you're in a position to be very close to the product, create something from scratch and you like that style of work. Really think through whether founding is the right thing for you, because it might be dramatically more effective where you don't have to work with another founder to test your vision.

And the economics are dramatically higher to have a founding stake than to have an early employee stake, but I recognize not everyone has the ability to found for a variety of reasons. And for that reason, I would just say, be very, very cautious.

Yeah, so just going back to what I was asking at the start, do you think this explains why I'm falling out of love with this company?

You know, the question that you asked was, I feel like the company was really fun to be at, at a certain phase. And now it's gotten to a different phase and it's less fun to be at. I think that that's expected because as we've talked about, we're moved from a very kind of nimble product inside the building type problem set to a later stage bureaucratic outside the building problem set.

And ostensibly you aren't as excited about that problem set. We see this most visibly with founders themselves. Founders are very gifted as we've talked about with creating product market fit to begin with. When they actually succeed, they can't change the product as effectively.

Now, as a company really starts to scale, their job as executives is not as being founders are actually taking their functional area like CTO or CEO, and that job is not a very product oriented job. And now if you're a product manager that has been hired, you know, this. That person might have a lot of opinion on product, but frankly, that's not their job.

And so when the companies go through these phases, they may have some identity crises around whether they even know how to do their role. And they may even prefer being at these earlier stages. And sometimes they change the product just because they can, because they have those roles and that's where they find interest.

But also because they don't necessarily know how to run the company or run the technology organization versus build early phases of product.

Catherine: Do you think there's a right stage of company for me? Like, should I stick to the lane of hypergrowth if that's where I'm at my best?

Nikhyl: So I actually think that you should be intentional about which stage of company that you should be at at this stage of career. That includes your current company or prospective employment, but it doesn't mean you keep that constant throughout your career. I just want you to be intentional that yeah, at this stage of career, I think I'm most interested in a later stage, more structured environment.

Personally, I went through a decade of early stage where I was mostly in founding roles. And then I told myself, look, I really, when I got to Google, want to understand how to master a more structured later stage, frankly, a more successful company. If I include that with my early founding skill, that's a very powerful combination.

So my point is I was intentional about later stage companies, but I didn't exclude the idea that I could move stages in my next role. And that's precisely what I did. After I had seen success at later stage companies, I ended up oscillating to hyper growth, so I did early, I did late, I did hyper growth, and then finally, at Meta I went back to late stage. And that's a key part of my advice here. Actually the most effective leaders in today's market have experience at multiple phases of company.

They're just intentional about getting it. Now, sometimes one's lucky and they started early and the company continues to grow and they continue to reinvent themselves that's rare. What's more common is to see the movie from multiple settings at multiple phases of the S curve.

And when you have that now, when you take on a new company, a new project, or you advise, or you're on the board, you've seen these different playbooks. And the next playbook isn't identical to the previous ones you've seen, but it's close enough to sort of merge your learnings from an unstructured environment to a later stage environment.

And by the way, as you're going between phases, you're probably also rising in terms of your leadership levels. So I was a director, I became a C level executive. I came back and I was a VP at a later stage. So each of those also has different viewpoints and vantage points. in summary, my point is, don't stay in one lane. If you can achieve it, try to accumulate learning and lessons from multiple phases of company, but be intentional at any stage of career as to which phase is the best phase for you, given your career objectives.

Most importantly, recognize that companies that are in the same phase, tend to have the same style of problem. So don't blame your company for being dysfunctional and assume that a similar stage company will fix those problems. Actually, most of the challenges resemble each other. And so if you are struggling with this phase of company and your current company, you're better off changing phases than trying to find something at the same stage of company.

Catherine: So I'm hearing that I should always have a sense of which stage of company I fit into the best.

This could change over time, but having that insight is super valuable. It will help me understand what I should deliver and the type of problems I'll encounter. Plus, it's a great way to figure out if I'm still in the right place or if it's time to explore new opportunities.

Nikhyl: That's exactly right. my hope is that all of you sit down and say, okay, based on the structure that I thrive in, based on the amount of hands on work, based on the kind of organization that I will be best suited for, I can pick one of these four phases. And then based on that, I can compare it to my current job.

I can compare it to potential employers and I can, for example, start a job search with just those size style of companies in mind. Recognize that that's not a permanent status that ultimately, once you succeed in one of these phases, you might choose to pick another one because elite professionals, the highest quality people in our industry tend to have successes at each of these four phases.

In fact, you know, some of the top product people I see getting jobs right now are those that have actually even founded companies. Been in late stage, seen growth, established organizations, but become scrappy and the combination of the scrappy, the scale, the hands on, the indirect is what you're looking for, but it's probably not going to happen all at the same time and product management usually has one or two featured requirements at any given phase of company and every given project.

So keep that in mind as you're thinking about navigating your career and navigating product management. And I look forward to hearing from you and hearing your comments.

Thanks for listening to the skip. If today's episode resonated with you, please consider leaving a review or sharing it with the people you know who want more out of their career. You can subscribe to my podcast on Apple, Spotify, YouTube, wherever you currently listen. You can also follow me on my newsletter on Substack.

And if you have questions or feedback, Email me at my first name, Nikhyl, N I K H Y L, at Skip. Community, or you can leave me a comment or send me a note on LinkedIn, Twitter, Threads, I try to answer each one individually. As always, I'm Nikhyl, and this has been The Skip.