The Widening Tech Career Divide: Big vs Small Tech

There's never been a time when people that work in big tech have been more different than they are in small tech. If you're optimizing for a big tech career, you're actually like increasingly becoming less relevant to small tech. And similarly, if you're optimizing for a small tech career, you know, you're probably becoming less relevant to big tech and that might be okay.

And I think the career guidance today's discussion is like, try to figure out which one you are and maximize the right one. Which isn't always the advice that I've given and certainly not what I've seen in the past few years.

Welcome everyone to the skip podcast. Uh, I'm your host, Nikhyl Singhal. This podcast is always dedicated to you and your professional career and getting you ahead. And you know, today's episode is kind of the end of year episode and I was thinking through it. And actually met, um, a really fun, interesting, uh, professional named Carly Malatskey.

And so today I'm going to sort of flip the table. She's going to be on the episode asking me questions about the end of year. And, and frankly, uh, I I'm just so thrilled that she was able to join me. She, uh, and I met through a mutual friend, uh, in the skip community, Jay Z. Uh, and I was listening to her story about, you know, what she's done at Stanford and then, uh, how she started as an engineer, went into an investor.

And now is going to move into founding. And I realized, wow, she's had like every job that you can have in like a five year period of time. So I just had to both listen, learn, and, and talk with her about this sort of how this crazy year has unfolded. You know, more importantly, I just feel like sometimes you meet people and you realize like you're all going to work for, for that person one day.

Okay. We're all going to work for Carly one day. And, and, and I'm so excited that she's We are able to join, uh, me today and, and chew through the, the sort of learning of the year. So, uh, without further ado, Carly, uh, welcome to the skip podcast. Nikhil, thank you so much. It's such a pleasure to be here. I'm very excited for this chat.

Well, and you're an expert in podcasts because you also, in addition to all the other great things that you've done, you, uh, host, she leads. Maybe we can start there. Tell me a little bit about your podcast. Yes, I will tell you that. And then I'm excited to switch, switch it over to you. But first, she leads a little bit about that.

So first, I love podcasts. I think it's a really incredible medium just to share knowledge and stories. I'm a huge fan of podcasts and what she leads. I talked to really incredible, powerful and just badass female leaders from all different backgrounds, whether they're Olympians or mainly tech, mainly founders of well known brands or C suite executives and just hear their story, how they got to where they are today.

The parts that I love about it is One, it's just gives the power of exposure. I think it's super amazing to once you hear stories of other people that you previously didn't know that it's even a path you can take. There's so much power in that. And I really wanted to open that up for people and just the comfort of knowing that, you know, no path is necessarily linear.

There's messiness along the way, there's lessons learned. So that's been incredibly fun. I've done, you know, close to 140 episodes, so it's definitely been a big passion project of mine. Nikhil, I want to kick it off to you. You have a couple of goals in today's end of year episode. Share with me what, what do you hope to accomplish with this?

I think that the sort of primary goal is to look back at 2024. I think it's been a year where we've seen more career change than perhaps in the last four or five years. And what I mean by that is, you know, if you think about the advice. That, you know, we all take, you know, in 2021, 2022, 23, and three, like, how do you get ahead?

How do you maximize career, you know, for about 10 years during growth, during the sort of zero interest rate, you know, career advice was kind of consistent, uh, you know, as go get the hottest company, get the biggest job. And then in 2021 to 2024, maybe 2023, I would say those two years when the market kind of started to crack, it was like.

You know, hide under the desk, you know, efficiencies coming, avoid the layoffs, try to become more of a builder, try to be more hands on and growth was just nowhere to be found. And now in 2024, and as we talk about what we're going to see is growth is coming back in huge pockets, but it's also not consistent with some people.

Are, you know, in a conversation and realizing their company is struggling and others are just sort of like, go, go, go. So it's almost like some of the sort of, you know, 10 year growth coupled with some of this efficiency stuff kind of colliding at one time. And then the second goal, I would say, as I've sort of thought back, like what's the one major reflection.

I realize that there's never been a time when people that work in big tech have been different, more different than they are in small tech. And so maybe put another way, if you're optimizing for a big tech career, you're actually like increasingly becoming less relevant to small tech. And similarly, if you're optimizing for a small tech career, you know, you're probably becoming less relevant to big tech and that might be okay.

And I think the career guidance today's discussion is like, try to figure out which one you are and maximize the right one. Which isn't always the advice that I've given and certainly not what I've seen in the past few years. I'm excited. There's a lot to dive into. So first, let's go more macro level.

What do you think has changed the most in tech in this past year, in 2024? The biggest thing that's changed is, you know, this sort of growth in AI has sort of changed the equation. You know, what we see now is a trend that, you know, perhaps is bigger Then what we saw when the web came out and what that's done is it's made it so that there is a set of companies and a set of skills that are in demand like they've never been in demand.

And what that's doing is it's making things like founding or joining startups. A heck of a lot more interesting than ever before. And it's also leading to venture rounds. I for growth companies, you know, companies with 10 people are, you know, growing at a hundred percent month of a month. And, you know, in your.

Work as an investor, you've certainly seen some of that. And so there's this sort of one piece of the equation in 2024 is this sort of red hot growth area that is pervasive. It's, you know, happening in companies that are building infrastructure. It's happening, companies that are doing power. It's happening in companies doing, you know, plumbing, like foundation models.

All the way up to SAS like companies that are going after specific business verticals and even consumer companies. So it's really just all over the map and it's crazy exciting. Then on top of that, you've got these companies that have been around for a while, who. Perhaps are heavily successful, really efficient, good businesses.

But for a variety of reasons, let's say maybe they're in fintech, those industries have been very much looked over. They've been very struggled to get out the door. Now you're starting to see those companies see an IPO window and they might be able to get out finally. And so you're, you know, the patient companies that have been waiting for essentially this next phase of growth are now going to be rewarded.

But then there's also many of these walking dead companies that still exist. Which have had huge dollars. So they're not like struggling for capital in the past. We wouldn't raise these huge rounds. And so you would be much closer to the, to the ground. But in this case, they have plenty of capital. And so you sort of think that they may be able to turn around.

But they're actually just not healthy companies. They don't have product market fit. AI is coming to further disrupt that and they're going to struggle. Now, the last point I'd make on the big tech side is that though big tech has these large organization structures, they have real estate investments, they have tons of people.

There are a certain class of problem that they're uniquely qualified to go solve because they have huge balance sheets, tremendous resources, perhaps massive distribution. So it's not a guarantee that big tech is essentially like all big tech products. They're all going to get disrupted by small tech.

You know, you see that they can work on innovations that are only unique to them. But it's just like, everything is sort of not what they used to be, is maybe my point. And given all of these changes that are happening in tech, how do you see this for someone who's choosing where to join? You know, how does this impact one's career choices?

Yeah, I mean, I think if you're generically saying to me like, Hey, I'm thinking about 2025 and you asked me the same set of questions as maybe you asked me in 2023, what I would say to you differently this year is I want everyone to think about whether you're ready to be a founder. Because I historically have said to folks, Hey, founding is not really for most people and it's not a particularly lucrative exit path.

It's just for those that are slightly dysfunctional that have to go and fulfill it right now, because founding is such a sucking sound because we've seen so many companies that are founded by folks who really want to found and who are founding for the right reasons. But it's just so market lucrative because of all the disruptions we just mentioned.

I think you have to kind of, every person listening to this podcast has to take a breath over the holidays and in January and say, Should I close the door on founding? Now, just to be clear, I don't think founding is for most people. So I'm not actually saying that everyone should listen to this podcast, quit their jobs and go and start raising money on found.

I actually just think that you have to proactively decide that it's not for you. Because of how positive of a path it is for those that have the skills and in my last couple episodes, you know, I've talked a bit about the importance of founding and, you know, in some ways it is a huge career unlock and there are some people listening to this.

Who actually are good professionals, but great founders, but they don't realize it and they'll actually have the biggest career unlock as founders. And those folks, I want them to proactively go through and think through it. Is the only way to test that if you actually go and found, if you take that leap or is there a way to actually get a good sense of whether you can be a great founder before taking that leap?

I mean, in some ways it's an emotional decision versus a skills decision. You have to emotionally be ready to sort of go through the process of betting on yourself without structure. I've said it in the past, like, if you're the type of person that thinks about things like promotion and, you know, leveling and status and liquid compensation, et cetera, founding is a tricky role.

If, on the other hand, you love the idea of not only not having a boss, but not having the structure associated with it, If you want to pursue something that should exist in the world that your company is struggling to nail, and you actually thrive in unstructured environments, these are clues that maybe you might be a good founder if you find yourself curious about newer products, if you spend a lot less time thinking about process and structure, etc.

If the idea of not having any kind of momentum or customer traction doesn't scare you, but it sort of intrigues you, these are sort of like, perhaps you should really consider being a founder and you know, there are halfway steps. I mean, I'm curious around your opinion around how to what the halfway step would be to become a founder.

But my hunch tells me that. Spending time with founders and seeing if it like brings you up or down is a, is a good signal. What, what have you found by the way, as you've been talking to founders, how do you tell someone's meant for it? I also was curious, like the noise of Silicon Valley, you know, and being so close to Stanford, which just breeds these great founders.

I think there's this the sexiness around it that I think is dangerous in a way it's a slippery slope because people you know see this and they see it glorified and they they have this belief like oh I want to go found not really knowing how it's incredibly hard and you know you have to be somewhat delusional to to want to be a founder so I think it's something that I've learned at Floodgate of trying to almost tug on like the, the true authenticity of the founder.

Like, why are they doing that? You know, you have these accelerators nowadays where, you know, you go into it, you, you can raise money now, money's flowing. And so people view that as validation. So it's hard. I think there's tapping into like, is there true persistence, you know, that they're, they're going to do this.

If it fails, they're gonna still keep doing it and keep running with it. But yeah, it's something that I think a lot about. And in terms of finding that middle ground, I think there are, there are ways to just be scrappy. Right? Just like get out the building, you know, that common saying, get out the building, test it, get user feedback.

Just being very scrappy rather than Having the glorified approach of, you know, pre idea pre everything, I'm going to raise a big round and run with it. I think there's there's maybe a misalignment of of true incentives and motivations. There's almost like a question around where does your anxieties come from, you know?

And I think that what I like about your note is some people, their anxieties is from, you know, I just feel like I'm not doing enough on my own. I'm not gritty enough. I'm not putting enough out there. The current job that I have is just not fulfilling me in a foundational way. And that person is sort of like predisposed to being a founder.

And if the thing that they work on doesn't work, they'll probably go after another sort of unstructured problem in some frame, maybe not as a founder, but in some ways. Then there are people that are very intellectual about the exercise. Hey, today, this is a good time. It might generate more return. It might be a good opportunity cost for me to like go through it.

Those people could be good founders, but they're not necessarily predisposed to being successful. My only note is that the window for those in the first camp is sort of screaming for those people to give it a shot, because those people will probably be more successful than the more structured job they wouldn't have been two years ago.

And. They may be able to birth something into the world that they never could have done before because there's just a ton of tailwinds to go after that process, you know, ticking off like the biggest career advice is you should proactively decide founding is not right for you. And the answer most likely is no, but I just want people to ask the question.

Yeah, that makes sense. Yeah, absolutely. So. I want to focus even before we get to big tech and small tech, because I think that's, that's alone just incredibly fascinating, but you're bread and butter around product management. How do you conceptualize what is most changed in PM in this last year? Probably the biggest thing is a trend that's been happening for a few years, which is, you know, we, and this applies in lots of different places, but it's essentially a story around growth.

You know, for 10 years, the industry grew a lot. And the product management function stood for helping assist and manage that growth. We've have product market fit. The company's growing. There's a big sucking sound on the company. Product management is the glue that ties engineering and sales together.

There in order for us to go after a second product line, a bigger version of our current product, go after more customer, get after the distribution and international, whatever, when you just need more people. Which means product management was a function of scale. And so that became the throughput of like, if you want to be a product manager, you have to be an expert at scale.

And by the way, you probably need to be able to manage other people who can do that. So this created all of these skills around how do you manage teams? How do you end up thinking about scale? How do you put in process all of this good stuff? It also explains why a lot of big tech folks who worked at scale were very much in demand.

Now, if you kind of fast forward as growth slowed, what we find is that, you know, the idea wasn't to actually bring in product management to help shepherd scale and expansion, we really wanted to make sure that it was a product function, it was a function that helped drive efficiency in the company. Hey, how do you prioritize more effectively?

How do you focus on just the right products? How do you connect what business really needs? To what the engineers truly need to do. So change the nature of the function, which meant the now product managers, when they go in for an interview, those that say, well, we managed a large team and look at all the growth that took place, they're replaced by, well, what was your opinion?

What was the story of what you build? How does it land? It is very much a hands on, like, where did you end up kind of pushing things out? That's a pretty foundational change. Compared to like a growth function. And that is only going to continue in the new, in the new year. As AI is essentially the ultimate and let's not scale with people.

Let's scale with technology. So the more hands on, the more closer you are to the bill, the better you are. Some of my friends who are applying for engineering roles. are, it's shifted from these, you know, technical interviews of code interviews, like live coding, solving these problems. And it's actually shifted to more of how do you think about this problem?

Like, here's, you know, something that we're dealing with in our company. Here's an algorithm that, you know, is broken. How would you solve it? So it's in a way, there's some parallels between product leaders and engineering leaders. And it's shifting more, like you said, to this more strategic, how are you thinking, rather than.

Tangible, you know, like how would you solve it with X, Y, Z? Um, so I think AI has been the biggest factor for that change. Yeah. I mean, this is such an insightful point, Carly. And I think that you could almost do an entire episode just talking about the importance of opinion. And I think that that can exist even in grade school.

Like what, you know, I I've been working with my son on some writing stuff and I was realizing like. The entire goal is mechanically, the actual words can be generated, just like as a product manager, the actual specs can be created as an engineer, the code may be able to be generated as a salesperson, a set of agents can go out and make the phone call, right?

Whatever you want to call it, that last mile is eventually now becoming more and more like a calculator was to a mathematician. And so now everyone's asking, like, what is your opinion? And I think that the big change that AI provides is that, well, there's a class of person who's very opinionated, but was burdened by all the mechanical stuff they had to do.

The engineer who wanted to build, who had an opinion on what the architecture and what the product should do, but was spending all their time doing the heavy lifting of like literally laying the bricks down in the foundation. Now is in a position to be empowered, but perhaps there's a bunch of people who are very good at bricklaying, but who had these very, very big jobs who didn't have an opinion and they're under exposure.

They're going to be revealed as like, look, if you don't have an opinion on what product is, the whole goal of product management is to be opinionated on the product. And this is the accelerated trend that we're seeing. For those people, the ones that maybe should be a little, a little scared in terms of keeping up with the new times, what should they do, what can help them still stay ahead and still kind of find a great job that, you know, benefits them too.

Yeah. I mean, that's kind of like the million dollar question, isn't it? You know, and I think that this is one of the gifts that being early in career has provided folks is that they, when you're early in career, you can kind of realize that the world is changing and you can kind of be comfortable in being hands on.

But, you know, the nature of your question is if you're far along in career and you're realizing that, look, I've X, I'm an expert at managing teams and people, and there's many people listening to this who say that that's my biggest expertise is where my joy comes from. My note is that's fine, but you need to be very much clear on the detail, how things are built and what opinions exist.

And if you're going to go talk to your next employer, you need to be able to articulate very concisely, not just like I was in a company and the ARR grew by four acts while I was there and I had this responsibility. As opposed to saying, I was in a team, here's the challenge we faced, here's the opinion that I had, here's how we ended up testing that opinion, here are the parts that worked, here are the parts that didn't.

As a result, I learned X, and now I'm able to apply it for this next setting. It is shows an understanding an opinion in a detail. And so in some of people that might be that maybe a small or more hands on role, which give them the ability to generate that opinion is right. Maybe it's rotating within the company.

Maybe it's transitioning to something. But the hilarious part is so many people are like, I'm going to take a step backwards. Because I'm a manager today and I'm looking at this company that's excited about me, but it requires me to work in a smaller team and I have to be an IC and I have to be hands on and I'm like, is it a step backwards?

Maybe in terms of comp, but maybe it's the biggest career unlock of your life because for the most part, you are not going to get more and more jobs of big teams, which require a less opinionated leader to shepherd growth. It's more around being very efficient, being very hands on, and if you can find an example of that and build a story around that, it could be huge, especially when you feel comfortable as the company scales with more people.

Yeah, absolutely. I love that. And, and we'll get into that too, because I think what you touched on as well is this idea where most people optimize for, like you said, salary or title or certain things where they're not thinking necessarily of, you know, how can this be. Overall additive in my long term career and where, where can this lead me?

So I think that's super, super fascinating. Yeah. That's partly, partly why I call it the skip. I mean, people ask me like, where does the skip name come from? And I'm always like, Hey, the best job that you have today is the one that sets up tomorrow. It's not the one that pays you the most. And the one that sets you up tomorrow is the one that gives you those skills.

And those skills are the stories that you tell. That'll be relevant for your next employer, right? So that's where it all kind of comes together. I love it. I love it. Okay. Nikhil, we've teased out big tech for small tech a bit, but first lay the groundwork a little bit, what differentiates big tech and small tech?

Is it mainly the size of the company? How are you defining it in your mind? You know, in many ways, the sort of magnificent seven or the magma companies, uh, are obviously big tech, you know, these are companies that are tech forward, like the microsoft's and the metas of the world. They have thousands and thousands and thousands of engineers and product folks and designers, et cetera.

They have multiple lines of business. They are global in nature, they're publicly traded, you know, the product management function is extremely well defined in this example, as is some of the business side, you know, clearly there are products that are in infancy and many that are global leaders. This is in contrast, and now we'll use the sort of small tech kind of nomenclature, which is.

Companies that, you know, have dozens of product managers, not thousands, you know, the PM management function over the last handful of years, and let's anticipate the next few years for that specific company is going to be shifting. What's needed from the function will adjust as a company goes through.

You know, finding product market fit to scaling that to being a global leader, there's just a change in what currency of value exists, you know, it's probably a privately held company, but it doesn't have to be, you know, this sort of tech company, but growing and figuring things out with hundreds of people, maybe 1000 or two, you know, Is that the high end and maybe, you know, very early, still trying to figure it out is this sort of small tag.

Obviously, there are companies that exist in the middle, you know, perhaps an Uber and an Airbnb and a block you can kind of discuss, like, where do they fit in and are they kind of small or big? And my guess is they're going to have elements of both that will come up. I think their product management function, for example, is going to be shifting.

They. You know, may not have the sort of layers of management that you would see in a larger tech. And so there's definitely going to be edge cases. But the reason why this is important is like half of the industry is kind of employed by big tech. 50 percent is roughly employed by the Microsofts of the world and their related cousins.

And then 50 percent are going to be employed by the sort of growth startup. And then the ones that are one kind of click above and below. So that's why this is sort of relevant is you generally have split the market in two, if you kind of use this nomenclature. Why is this important for people to now consider for product leaders, PMs to consider?

In their career choices, and this is probably the most important point of this episode is that I want people to appreciate. These are just different jobs. And I don't think that we have established in our industry that these jobs are as distinct as they are becoming or have become. And so let me lay out the case really quickly.

I think that like a really specific example, and I'm going to go through a handful of these, right? So Clearly compensation is just vastly different, you know, compensation, for example, when you're, you know, in a big tech company, it's highly liquid, whether you're getting equity or whether you're getting base salary.

It is essentially the same instrument because you could sell it every quarter. So you're just getting a block of comp in different ways of being paid and that's turning into whatever you're going to make that year. You can choose to hold the equity or not. You could either take that cash and you can buy stock.

It's a it's effectively this thing that couldn't be more different than small tech. In small tech, let's say a leader, half their comp or more, in some cases, in the extreme case where you're a C level executive, 80 90 percent of your compensation is in equity. But in big tech, you can turn around and sell it every quarter, and in small tech, it may turn into zero.

That, like, could not be any more different. Yet we talk about things almost like the same, like, for example, there was an article that just came out recently, just related to comp and the big headline on the article was like, equity is no longer relevant. People don't care about equity. And I'm like, are you insane?

How could you make that comment? Because if you're working at big tech and 50 to 90 percent of your salary is in RSUs. And those RSUs in 2024 doubled or tripled in value. If I took, told everyone at Microsoft and Google and Meta, Hey, by the way, we're just going to take all of your equity away because it doesn't matter, you would have literally revolt.

But then this headline was very much like, well, equity doesn't matter as much. Yes, for wounded small tech companies. It probably less relevant if you're an IMC, which is the vast majority of perhaps people that took that survey. But if you're a leader, you would not be there. If your market rate's a million bucks, you would not be there if you know, you're making 200 K and 800 in private, you know, stock that's kind of relevant.

So like these terms matter. And I think that we're just so conflated right now, which is, Oh, they're all jobs, whether it's a Google job or the hot job. I want you to go even deeper. So beyond compensation, what are the other key considerations that people should recognize rather than kind of lumping them all into one, one together?

Yeah. And so as we're laying out the case, you're going to increasingly start to feel like, yeah, okay, now everyone gets it. These are super different paths. And then once we lay out the case, the punchline, and I'm going to signal it now, and then we're going to come back to it, is that the likelihood is you're just going to be better at one versus the other.

That's the punchline. And so going into next year and thinking through career advice, you should sort of say, okay, well, maybe we've closed the door on founding, but like, Hey, you know what? I'm just like a great big tech person. Or I'm just like a great small tech person. And so as we're listening to these criteria, we're trying to pick out which one makes sense to you.

Like when people think about worries, like, Hey, what are you worried about? When I talk to big tech folks. You know, 80 percent of their worries is around the velocity of shipping and promotion, leveling committees and whether or not they're going to be seen, right? So everybody in big tech, because the system of progress and progression.

Is very much around advancement, literal advancement, title. More calm, the actual idea that they are accomplishing their level five today. Maybe there'll be level six more. That's really the conversation. So if you bottle up the hundreds of conversations I've had with big tech folks, they fall into like a frustrated, not shipping enough.

I worry about my promotion. I worry about this upcoming word structure change that's going to happen. And if this doesn't happen, I'm going to look for a different role within the company. Okay. So that's the conversation. Not a single one of those things I just said ever come up in any sell tech conversation.

Because they're very rarely worried about promotions and leveling. It comes up occasionally, but usually these companies are smaller and the fear is not that they don't care about those details, but they really care about competition running out of cash, whether they're going to be able to succeed in the marketplace.

They worry a lot about. Is the function need the skills that they have sometimes in an unhealthy company. They're very worried about whether they'll be able to move forward in a healthy company. They're worried if they're going to keep up. The managers keep changing, not because of work changes, but because of growth, you know, there's trying to navigate product market fit.

So they're throwing lots of code away. Most of the challenges are just broadly speaking, not even related. To the structured challenges that I described. So my note is some set of people are like very oriented towards one class of problem. You know, like I see myself as someone who likes a structured setting and I want to see an advancement.

Perhaps they did well in school because they're, you know, they have this sort of structured mindset and the class of problem and big tech, like is the kind of problem they're used to solving and used to having anxieties around. While in the other case, when you're in small tech, you know, you're very much trying to sort of create a product that people like, and then hang on for the ride.

And those types of problems are a whole different set of skills that you have to master. And so the worries are quite distinct. And so you can see yourself, which ones create worry in you. Will help align yourself into like, Oh, which column should I end up gravitating words? How do you differentiate between this is my worry purely because this is the nature of the company.

Like I have to worry about it because it's bigger. So velocity matters. Promotion matters versus this is my like true motivation. You know, how does someone recognize I actually could excel in an environment where it's a bit more scrappy, you know, worried about a whole different array of topics. Rather than like, this is just my everyday work.

I'm swamped because this is what I do for a living. Maybe the other way to look at it is let's say that you're really struggling with promotion or you're really struggling with title and getting ahead, et cetera. And then I'd say, Hey, you know what? Imagine a world where you didn't have a title. Imagine a world where promotion was irrelevant.

Imagine a world where the way you would gauge progress was a lot less tangible. How would you react to that? One class of person is like, well, I would struggle because I wouldn't know how to measure myself and see myself as successful. That is essentially like it's a taking classes without grades. It really freaks me out, you know, and on the other hand, maybe directly to your question, there's a class of person that's like, great, well, I would love it.

Because I would just want to master the learning and just do good work. I don't actually care about the grade. The grade seems to be somewhat arbitrary. I'm happy to be a member of the technical staff, never get promoted. As long as I feel like I'm being fairly compensated and being seen. And there are literally people.

That are like working in the system that are only working in the system and trying to master it because it's there and there's a class of person who needs it to be there and that's where they thrive. And when I go to big tech and I talk to people about 80 percent needed to be there, but about 20 percent are like, well, it's there, so I might as well do it.

But those people actually do well in most environments. They just want to, you know, whatever the currency of value, they just want to be able to master it. So my note is, you have to almost ask yourself, like, which class of problem really brings out the best in you. Even as I was asking that question, I also realized like, you're right, maybe it's the type of person who is striving for that promotion and is just looking to get to level 5, 6 above.

They're the ones that, that do, you know, strive in that environment and they embody that structure versus someone that's, you know, more excited and maybe worried about velocity, but more excited about, you know, just getting shit done and, and shipping a product, then maybe they're like, okay, you know, I can actually strive in a, in a small tech environment.

That's kind of how I conceptualize it. Yeah. So I want to build on that point. Cause I think that's actually a tremendous, um, insight. There are always going to be worries and maybe this is actually a better way of framing this. The question is which one bugs you more and keeps you up at night. So when people call me and they're like, I'm bugged because I did a great job because I moved, moved a project from this point to this point, but I didn't necessarily have much of a product and opinion, but the main thing is.

I just don't think that I'm going to get promoted because the committee doesn't see me. My manager isn't really advocating, blah, blah, blah, blah, blah. That's what's keeping me up at night. That person should work in big tech. Then there's a class of person that's like, you know, I'm bugged that I'm not getting promoted, but what really bugs me is that we're moving so slowly and I just don't think that the thing we're building is even relevant.

And I think the flip exists in smaller tech, where in smaller tech, it's like, yeah, I mean, the company's growing and all that. But I just don't feel that I'm managing people fast enough, or I think I need to have a bigger title, or I feel like, you know, I'm not getting seen in the way that I see myself.

And I'm like, well, but you're building a bunch of great stuff and the company's just coming along. It's great for your career. It's setting you up. So the point is, like, which worry keeps you up at night the most? Might be the best way to characterize this point. I love it. And do you think that, you know, someone may, may come from big tech and purely want to go to small tech because they want to master both?

Like in your mind is a great product leader, someone who can master both? Is it very additive to your career to be able to master both? Or how do you, how do you kind of reconcile that? Let's talk a little bit about the core skills that are needed to succeed in both. And then I think what we'll find is that, you know, and I certainly was able to do well in both environments.

So I actually think that it is career additive to do both. And I do think it helps to oscillate between the two. So let me, let me plant that out there. So to say that, look, in a perfect world, if you're listening to this and you've mastered big tech, if you can master small tech and then bounce between the two, it will maximize your career impact.

However, I'm of the belief that it's increasingly rare for people to do that. And I'm of the belief that you can be successful in just picking one lane. And just staying in that same lane for multiple roles. And I think that there's a worry I have that people that are never worked in late stage tech companies feel like they're not as valuable and their brand will always be a concern, but when they come to big tech, they struggle.

And similarly, there's a lot of people who have been excellent at late stage and they should stay there. But they have this complex that they have to go to small tech, they have to be the chief product officer or something like that. And those people struggle. And I think that's actually a damaging move in both directions.

So now the core question that you might ask is, well, what skills, why would that happen? We've already established there's a totally different jobs. You know, they have different talent profiles. The people that work in these later stage tech have different skills. They're at different levels of career.

You obviously, if you're in big tech, you stay for multiple years. Oftentimes in small tech, these companies aren't even multiple years long. You know, the tools you use are very proprietary and big tech and very, you know, the, the latest tech products are usually internally used in small tech. So the environments are super different.

But the biggest thing. Is the note that I make is big tech companies have a lot to protect because they've succeeded. They have a huge set of customers and products that are world renowned. Okay, when you have a lot to protect, you are very, very reluctant to change things without measuring 87 times and then cutting ones.

That is essentially your model. So everything around building product, especially in product management is Becomes an inside the building challenge. Hey, I have to work on an idea and I have to build it, but I have to manage the inside the building headwinds to get things out the door. Now, that might be frustrating for some people, but it is with reason, if it turns out that it was incredibly easy just to change the product that are in the market, anyone can just check in code or come up with an idea.

The next thing you know, it's a different product. You know, it was blue on Monday. Now it's pink on Wednesday. I think that you would imagine that company is highly brittle. Because you have thousands of people that have thousands of ideas and you have to protect, but if your entire function now is around protecting and measuring what's actually going to be most valuable, you're going to have a different skill set needed to get something out the door.

That skillset needed is actually not that relevant to a company where most of the energy is spent listening to customers, coming up with ideas and changing what's in market. So the opinions that you may hold when you're at late stage is around, how do I influence the people around me? So that I can actually deliver the thing that I have to deliver, but the opinions that you hold in small tech are much more around what does the market need?

What is the challenge of our current product and how do we shift it? So currently you can see, like, that's a totally different mindset. It's a totally different skill. That's a certainly a different background. And so my note is that just to not casually just describe both of these as the same kind of product management challenge.

Seems crazy to me, but that's kind of how we talk about it as an industry speaking just on the the skills front. Are there similarities between all of these PMs? Is there something that they both share in terms of excelling at big tech and small tech? Well, they both burn out. That's okay. I think that one of these other kind of fallacies that people have is that big, big tech jobs are cushy.

How many calls have I taken this year? Where people call me and says, you know, boy, I'm at this small company, I know it's a lot of stress because we're not sure whether the equity is going to be worth it or, you know, we, you know, have to turn around to cut the staff, it's really hard, maybe I should just go to a big tech and I should just earn the big liquid salary and just kind of phone it in and I'm like, I don't know, when I talk to folks in big tech, they are stressed out.

They're taking meetings all the time. They're dealing with a lot of work changes as well. They are under tremendous pressure because the speed in which AI is moving is creating a lot of pressure that people are like, look, we need to go build, we need to take advantage of it. So everyone is at high pace.

So the one consistent theme that exists across all of these is that the pace is high, whether you're in big and small. We've established that the skills are different. You know, you have to think about, oh, you know, if you're in small tech, you have to create something for the first time, while in big tech, you have to figure out a way to change something that's working right, very different skills.

So we've established there's a bunch of skill gaps and differences between the two, but you're definitely going to be working at high pace and the concept of, you know, core skills like prioritization. Collaboration, you still need to work with other people. You still need to influence others. It's just the way you're doing that, the objective function, is are you trying to change something that's clearly working or are you trying to establish something that's never worked in the past?

Couldn't be more different. So, Nikhil, I'm very curious what your opinion is on this, which is. I still think there's this narrative where many people assume that the best PMs actually work at big tech companies. And it's pretty understandable why, because these big tech, you know, they have the biggest brands.

With LinkedIn, you want to, you know, collect that bag. There's all these elements to it that are super important. And brand seems to still be quite important in tech. It's almost like, you know, Trying to get into a great college, you know, it looks great and it's important and it kind of reflects who you are and your skills.

Do you still see that being very relevant today or how do, how should people conceptualize that? Yeah, I think that this question brings some amount of internal turmoil to me. Because I think that this is a questions that answer might be different in 2026 than it is in 2024. And it is very much different than it was in 2021.

So, and I think it's very predicated on the fact that there are differences in skills that exist. So I think let's go back in time for a second, you know, between say 2012 and 2021, during this sort of growth phase where there was like low interest and all this, like, you know, money going in, we established that product management in particular, but generally the industry was in such hyper growth that most of these professionals that were brought in were not people with founder and builder mentality.

There were people that came from, you know, established companies that had sort of seen the Promised land, just to be very concrete. A bunch of people from Google, a bunch of people from Meta, a bunch of people from Microsoft ended up joining these growth companies and they, you know, and I was actually one of 'em, they joined these hot growth companies, as you know, number one.

Number two, chief product officer, head of product, et cetera. And the idea is that, look, you've seen the movie when things are working at scale, you should bring that special sauce to us as an organization because we're growing as well. Okay. 2021 came along. And the companies ended up having to cut back founders had to be a lot more hands on the people that they brought in weren't necessarily opinionated on where the product strategy should go, or they were opinionated, but the founders felt like the town wasn't big enough for two opinions now.

In most cases, most of those C level executives were perceived as not doing well. So now when you're looking for a number one in a hot company, I don't hear that they are like targeting folks that have had expertise at Meta or Google or Microsoft or Big Tech. What they're looking for is the hands on, I see.

Who's opinionated, who can start building out with the founders and add just the right amount of process. And if you think about it, it makes sense because what's your skill when you're a VP or director at big tech is managing large organizations and protecting. Very successful products. That's like, could not be more opposite.

And so when the jury came back and they're like, how good were these folks? The results weren't great. And so when they did these efficiency layoffs, a lot of those folks got cut along with the rest of the team and the founders became, you know, CPO as well, or they created the CPTO functions where the founder technical ended up overseeing it and they ended up becoming a lot more efficient.

So this is the trend now back to your question. Your point is that, well, you know, if I'm mid career, isn't it important to grab that brand? Because it shows that I have expertise. It's like, well, perhaps, but if the North star is that if you succeed in big tech, you're have to stay in big tech. And that might be our big statement today is like, if you become the director and VP of big tech, you're You're essentially mastered a very important skill that applies to a very specific set of companies.

It does not apply to being like a head of product at some company that's building a bunch of stuff. And maybe there are these companies that have become so significant. That have become so successful that they down now do need a team builder. But my note is if team building is a top thing that you're having to master, as well as ability to get things done internally, it doesn't really necessarily means you're going to be a great, you know, small tech leader.

And so in some ways you have to essentially grab brand, but not at such a senior level that you can't take that small tech job, or you have to essentially stay in big tech. But this, this notion around how to think about the lanes are almost like separate enough that you have to find a way to get a little bit of experience and see the movie.

But not become the orchestrator of that, if that makes sense. Well, Nikhil, it's, it's funny you mentioned, we've seen it with one of our portfolio companies where I think. Internally, like the mindset is changing with AI, like with everything that's happening with AI, where they've noticed that the junior engineers actually are way more forthcoming and excited about these tools that allow them to move faster, whereas the more senior managers are actually a little averse to it, you know, and they're like, No, we have to do the structured way and and go about it in a certain way.

And, you know, so there's, there's somewhat of a shift happening. And the reason why I say this is It's similar to what you said, where now they're actually more excited about hiring these ICs, these junior engineers who, you know, have this kind of concept of where are we going? What tools can we use that could really speed up our process and be more capital efficient?

So there's something like beyond product, beyond all of this, I've seen it with one of our, one of our companies for sure. Yeah. I mean, it's like the power to the proletariat, right? What you're describing is the biggest story of 2024. Is that for a while, they were like, let's get a lot more efficient. And now it's like, well, the only people that seem to have opinions are the people that use ICs.

I mean, there, there was these hilarious realizations that I made and it comes up all the time when larger tech organizations where people were like, it seems like the way this works is the IC3 or the intern comes up with a product idea, particularly in consumer. Because that's the people that use these products the most.

And then there's all these layers, almost like this gauntlet that they have to run, where it's like, you have to convince that person and that person's manager and that person's manager, manager, and all of those people, they don't feel like they're getting paid to create new things or to ship new things.

They get paid to protect the old thing. And so the amount of energy that is required, the skill required to get something out of the door is very profound. Now, your question was, but don't you have to work in big tech to be successful? And my note is, well, maybe that brand is atrophying. Maybe that it becomes more important for you to be in a successful environment.

Now let's pretend that we were in 2025 or 2026. And now you're like, wow, look at all these major unicorn companies. And they're all built with dozens or hundreds of employees, not thousands or tens of thousands. They have like really efficient product management staffs. They have like one manager, two managers, you know, I think open AI only recently started adding managers into their structure and product management as example.

Now you're going to essentially say, well, is Google or Meta the company that they are going to need to work for in order for them to be essentially badged, to be able to get into the hot company? Probably not. Now, does that mean that those people are screwed from a career point of view? Absolutely not, because those companies will continue to be quite successful.

They're just going to have different types of needs. And so all I'm trying to point out with this episode, and perhaps it's slightly long winded, Is to say that you more and more need to kind of realize that you're going to optimize one or the other, not necessarily both. Increasingly, it's going to be rare to see someone who's exceptional at both of these.

And so my counsel is try to figure out based on what we've talked about, where you're at your best, what problems that you enjoy solving and don't feel like if you're good in these growth environments that you're somehow doing a disservice to your career by not taking a tour in the later stage environments.

Similarly, if you're good in these later stage environments, but you're frustrated, you're not building enough. You may not actually succeed at all in an unstructured environment. And we saw some of this happen when we saw the pullback of growth. And in that case, maximize the hell out of late stage. So maybe going from meta to Google is your career move, or maybe optimizing your meta career for a dozen years or beyond, but taking multiple roles within them, do stuff that's early or mid or late.

Those are fine models. But this oscillation thing happens in mostly at an earlier stage of career, because at some point it comes very hard for the VP at late stage to be the number one person that a growth company would want. But those might be the most desirable companies in the market in the next couple of years.

Absolutely. That was, that was great. And I know we're going to, we're going to wrap up soon, but. Nikhil, is there anything that maybe we didn't touch on that you really want to include whether it's, you know, advice for people, the biggest trap people fall into when they consider their next career move, whether it's big tech or small tech?

Well, maybe one thing that we didn't talk about, I made this sort of note that, hey, The market's kind of like divided into big or small. And I think that then, then I talked about these edge cases of, you know, early stage companies that are just getting off the ground or sort of like, you know, variants of the small tech.

And maybe there's companies that have been around for a long time or that are very large, that have multiple products. They like the Ubers of the world. I mean, they're going to look closer to big than small. I think there's also companies that sort of don't fit into either category. Like I have learned that non U.

S. based companies sometimes are just structured differently and they have different work. You know, if you work for ByteDance, for example, I'm not sure how much of this would necessarily apply, you know, as an example, that company has a lot of the sort of. Market power and distribution and platform that a large tech company has, but actually in some ways is very efficient and less structured and has some of the different challenges that small tech has.

So non U. S. company, also a small tech, non U. S. European company might have some of the big tech tendencies just because of the way the culture and the structure is aligned, right? So. I would say that sometimes you've got startup, sometimes you've got non U. S. companies, sometimes you've got non tech companies, like say media companies or manufacturing companies that are product managers.

In fact, when I first started scripting out this episode, I was thinking about like, Hmm, the third category is actually like non tech that wants to be like tech. And that sort of has its own behaviors. But I realized like, Hey, I don't know enough about that, but I know enough to know it probably doesn't fit into this category.

So I'll definitely caveat that if you're in a company that's not doing well, if you're in a non U. S., if you're in a non tech trying to be a tech. Not all of this is going to apply, but for the vast majority of my listeners, they're sitting into tech companies trying to figure out like, how do I career advance?

They're frustrated that they're not in the other lane. I'm like, well, that might be a feature, not a bug. And then that to some extent should help you think through this question of like, which is the lane I want to master. And then which one is essentially the right one for me. I love it. And one of my, at least just, you know, listening to you, one of my biggest takeaways as well is two aspects.

One is when you, when people are considering this big tech for small tech, one question you could even ask yourself is what we talked about, which is almost which worry is most prominent for you. You know, and I, I think that's a really, it's, it's tangible, you know, and, and you can kind of start to question yourself, is it because we're not moving fast enough or is it because I'm struggling to get promoted?

Like, that's a really telling sign. And not only that, I think, like you said, it's very easy to lump all of it together, but, you know, you highlighted very well that it's just strikingly different and skills, compensation, all of these different considerations. And then beyond that, I think we're at a really compelling time in technology where.

You said something where now we're not scaling with people, we're scaling with technology, and I think that's so powerful, and I think that'll continue to happen, and what that has already happened in terms of career and hiring is that now your opinion matters, matters more than anything. You know, and not necessarily what you're doing with it, but it's how you're thinking and how, how you can kind of implement that thinking into an organization, I think, is now becoming very, very powerful.

So, Nikhil, this has been, this has been excellent. This is so fun. So well said, Carly. I mean, you pulled out all the insights, um, from today and helped me really straighten out my thinking. As we head into the holidays. I hope you have a great break and I hope you come back on the show. I think all my my listeners and I certainly would would value your insights as you go through these journeys around career as well.

So thanks again. Absolutely. Absolutely. Thank you, Nikhil. Thanks for listening to the skip podcast. I have a couple asks for you. One is please, please follow my content on YouTube. We're on any podcast platform, Apple, Spotify, et cetera, that you follow. Um, I tend to update about once a month on career guidance that can help you accelerate your tech career.

Second, it really helps when you forward this content to other people in your life that are actually trying to optimize their professional career. And if you have career questions or comments, please email me at Mikel at skip dot community. I read each one of those messages and try my best to answer them and help each and every one of you with your career until our next episode.

I'm nikhyl. And this has been the skip.