Is my next job at a startup or big tech?

Nikhyl: Hi, everyone. My name is Nikhyl Singhal. I'm your host for The Skip podcast. Today's episode is another in a series of our coaching calls. Our coaching calls are when someone gets in touch with me with a question that's on their mind related to their career. And today's episode, I was approached by a director at a growth company that finds themselves slowing its growth.

And what he and I chatted about is how to think about next steps, what jobs make sense, and how to think about different stages of company. So what I love for you to pay attention to is when someone's at a career crossroads, how do they think about their current job? And in this case, because the person has been in a growth company for 3 years, how do they think about the stay versus leave decision?

What does risk really mean when it comes to startups? Everyone talks about, hey, startups are risky, but we really get into some examination as to what does risk mean for this individual specifically related to compensation. And as you've known, if you've followed my podcast, compensation is one of those tricky topics but we actually talk about numbers and what the expectations of this individual is and how does that map to their job decision and their career framework.

And lastly, we spent a bit of time on stage of company. I always prefer when we're thinking through job transitions to look at stage of company, not name of company. It's not a hey, Meta is good or Uber is bad type conversation. It's much more around stage of company and as late stage, mid stage, early stage, really the right choice given your specific situation.

So we map the career decision to stage of company, and then a lot of the episode goes into late stage and really thinking through what are the myths associated with joining a late stage company, a big tech environment, and what are the realities? What are the advantages? And how has that shifted over the last couple of years as growth has really changed in our industry?

So, as a reminder, all of these calls are anonymized and edited. And so we'll switch directly over to the conversation we've been having.

Guest: What's on my mind overall is, I've been thinking for a while about my current role not being the right fit and trying to figure out what's next. I don't see myself getting excited about starting in that new role in this company that I feel like I could give the long term effort that I would want to. So it felt like the right time to leave. I've been mainly in, I guess I'll call it the soul searching and planning phase of what sorts of roles I think I would want to look for for next year. One of the things that I feel like I've been trying to internalize and then work through is that the industry just looks different right now than it ever has in my time looking for jobs.

And to me, that means that I should also be thinking about what I'm looking for in my next job and how to find that next job differently from how I have before. So mainly looking for thoughts and advice on A, I guess, my own perceptions on what the industry is right now and what the implications are for the roles out there where my initial thinking has gotten me is I think that I'm interested in joining a public company in all likelihood.

Nikhyl: What led you to believe that the sort of role at the company wasn't the right thing for you from — from a career point of view. And the reason why I want to know that is, I think it helps a little bit of a clue as to what next would look like.

Guest: There were a couple, a couple reasons why I was feeling dissatisfied in my job, and I'll be really candid with you. The company was scaling so fast through COVID, numbers were going up, and therefore team size was going up. and it was one of those moments where you say, we hired ahead and we hired optimistically.

And unfortunately, I think that we also hired really top heavy. Look, when I joined, I was only leading a team of three PMs. At the height of our growth, I was leading a team of 10 PMs and managing managers and then scaled back as we added more leadership.

And that didn't bother me at the time but as we started to be more critical of headcount, manage people out for performance, and by default, not backfill and things like that, I ended up in a place where my team was only three people, which, to some extent, it's not about scale of team I'm not looking for the largest team possible, but it was more so about scope of problems that I was then focused on started to feel narrower and narrower and was starting to feel stale to me.

And then the second thing that culturally happened through the shift is part of the reason that I joined a company at that phase is because I wanted to be close to the executive layer, and I wanted to be part of the decision making that was about both company strategy and then organizational strategy.

And when we brought in the additional layer of leadership a year and a half ago, I felt a really, really clear change in the amount of transparency that I was getting into both of those things and the extent that I could be involved in each of those. And so I think that was honestly the bigger thing for me beyond team size, was just the feeling of what were the problems that I was getting to engage with on behalf of the company.

And that layer really felt like it disappeared and it was just this newly narrowed scope that didn't feel as challenging or high leverage to me at that point. One of the questions I always ask myself when I'm taking a role or choosing to stay in a role is what do I feel like I'm uniquely positioned to learn here that I wouldn't be getting the opportunity to learn elsewhere.

And in some ways, when I'm looking around at other growth stage companies, looking at my friends working at other companies, I'm seeing more pattern matching than I am things that I think would really challenge me or get me to learn something in a different way by joining another growth stage company.

So that kind of pulled me to there's either going really early stage. Or going late stage, liquidity and compensation is a meaningful consideration for me, kind of for the first point in my career. Where when I've made my last career moves, I've had way higher risk tolerance than I do when I'm thinking about my next 3 to 5 years and moving into life stage purposes.

And so it's harder for me to wrap my head around joining a series A, B, C company right now. Even though I'm seeing a ton of opportunity there, I'm seeing so many of those companies hungry to bring on product leadership. but I'm concerned about the risk level.

And so on the flip side, going to a late stage company, I'm curious about it. I didn't necessarily think I would join a later stage company until later in my career, but if I think about at least the next 2 years, the industry looking substantially similar to what it does today, might it actually make sense for this to be the moment that I jump in and see, is it the right fit?

What do I learn about it? what more information do I have? also, in some ways, I'm seeing later stage companies doing some of the most innovative work at this point, which I think maybe some of my own biases have prevented me from even, thinking about going to the Googles and the Microsofts of the world before.

When I look around and I see so many private companies in what feels like existential mode. Even though large companies are clearly having to change the way that they operate, you're still seeing more innovation, more willingness to invest in bigger bets. in addition to, tightening up the core honestly, I think some of the most interesting product launches in the last year have come out of Microsoft.

That's what's changing my mindset and what's pushing me to at least start my search on the public company side of the spectrum. I feel like I at least need to focus my energy and trying to do that at the same time that I'm also exploring early stage opportunities just feels really tough.

Nikhyl: I agree that kind of looking at a similar stage of company as your last two has two negative impacts.

One is the point you made, which is less to learn, less to prove a little bit more common. I think that if you found a role that's substantively larger than your current one and it had reasonable culture, it might be a pretty interesting opportunity. But I think that because the market has retracted and because a lot of growth companies are X growth companies, which is very similar to the experience you have today.

I think that's going to be a bit of a diamond in the rough situation. Those companies that find themselves looking for sort of a manager of managers and that are still in growth mode or starting to pick up growth again, we'll go to an internal candidate more than an external.

So I think that the efficiency of that search is going to be very low. You'll get a low ROI on that one. The early stage company, the sort of pre product market fit, looking for the first product manager leader in the organization, your series A to series C example, I think is actually the most promising in terms of your candidacy, your ability to drive impact and probably joy.

I think that the only concern is going to be primarily around liquidity of comp and time window of comp. And so I think that's the thing to drill into if you felt like, look, there isn't any realistic way that I'd be able to take a 60, 70 percent of my income in equity that might not unfold for multiple years, then I think that for the reasons you mentioned, might want to focus upstream on your search.

On the other hand, if you said the risk and use that word risk, I think it's a little too risky to go after early stage. If your point is that, hey, that risk is that equity wouldn't be meaningful over any period of time. I think that's less likely. I think that there is lots of healthy early stage equity to be granted today because expectations are solid.

Those companies are younger, you know, the market will recover and start to open up in the next few years. And those early stage companies would be great. So I think you want to be a little counter cyclical and you in this case, the story would be look, I was in a growth company. It stopped growing. I went to an earlier stage and by jumping on to this new ship, you know, while that company sort of flatlined and expectations was inconsistent.

I have this great, you know, upswing and I was a number one. And that number one position, I had a dramatically larger equity stake, and that turned out to be meaningful. So I'll pause for a second. Do you have and it’s fine if you do, but do you have liquidity concerns? And is that what's driving you away? Or are you just worried about startup equity generally?

Guest: I have liquidity concerns. This is again I mentioned, like, this is the first time that that's taking a meaningful role and how I'm thinking about next phase of my career. Given that I'm at a company that still hasn't gone public and there's uncertainty around what the timeline and value of that liquidity will be. I do feel need to get some more certain and nearer time horizon liquidity.

Nikhyl: What is your kind of baseline expectation for what you need in an annual basis in terms of cash or, you know, just near liquid income is probably the better way to ask the question.

Guest: It's not that I need money to pay my bills this year. I'm heading into family planning mode probably on the 3 to 5 year time horizon. It's more so about being able to predictably save more to be able to prepare for that.

Nikhyl: Let's say that we found a role. And this role checks all the boxes in terms of joy, culture, ability to have impact. It's similar as team size of what you have today. So it's two or three people but it's a sort of hot series B company.

You felt like that's really innovative. It's really early stage. It's doing great and they love you and logistically, it works out. It's not like a crazy role overseas or, you know, the founders feel like there are people that you can really gel with the sort of comp is, you know, 1 percent of the company, but there's risk as to whether that will pay out, but it's like a quarter million dollars annually in terms of cash comp.

Now your kind of expectation is that, hey, if things work out the way it is, it's like a 1 to 1 and a half million role, maybe as much as 2 million of the company kind of does well annual, but of that 1 and a half, 2 million, you know, there's some risk that you'll never see it and it'll take a years to unfold, but at least the baseline is a quarter million and companies raised money and they're paying their executives at a reasonable rate.

Does that feel. Like, uh, actually a quarter million is great. I was worried it was going to be like 50K. Is that in the range or you're like, no, no, I feel like I need 5, 6, 700 to sort of you know, make a meaningful dent in my savings.

Guest: Based on where I am mentally, I think that I would be more comfortable being in a role where I'm confident that I predictably have at least 5, 6, 7 coming in annually.

Nikhyl: So the reason why I was poking on this is that I just want to make sure that we're not dismissing one of these stages because of potentially the sort of marketing of that stage as opposed to the reality. I'm with you that it's pretty rare to see early stage company. That can provide that level of liquidity.

And there are some squirrely things that, you know, companies do around secondary offering of equity, et cetera. But those tend to be a little bit further along. You don't want to be in a situation where your cash situation is dramatically different from your peers, because then you'll always be, a little bit across the table.

Maybe you'll be changing equity and they won't see you in the same way, et cetera. So, so let's flip to this sort of later stage kind of question that you were asking. I think it's insightful that you mentioned that there is more opportunity to do longer term or innovation. The few things that I would just quickly note around career planning as it goes to these later stage companies is, I definitely feel like oscillation of stage.

Is the right career model, than planning, like start early, then do mid, then do late every decade. I think that bouncing back and forth, it really kind of allows you to grow a bit more quickly. And so what happens is, you know, in your situation, the story could be, I took 2 growth settings and I ran them up, saw the what it was like to sort of manage the product, drive some innovation.

Then I went late and then I came back to growth. And then I went maybe and did something early as a number 1, and you can imagine that in each of those are sort of step functions and learning and maybe new kind of levels of leadership within those organizations. So, I always subscribe to that. I think it could apply in your case to early, or it could apply to late, but it's, as you point out, less valuable to, to stay in that sort of growth stage. So I think that made sense. I think that when you go to later stage companies, unlike earlier stage, longer tenures are kind of prerequisites. And so your note that, hey, my prior role was a 5, 6 year role. My current role is a 3 year role. That's an important element as we're talking through this, because if you're a person that comes in and you're like, hey, I spent 1 to 2 years.

And then in the next job, I took 1 to 2 years, et cetera. You really find yourself taking 1 to 2 years to acclimate yourself to most of these later stage companies, particularly if you've never worked there and you're coming in in more of a leadership capacity. Because there's just a lot of complexity to product lines that take a while to absorb and, you know, there's an adage that a lot of times it takes 6 to 12 months to even just get the telemetry, right?

So, my gut tells me that you need to be in store for a slightly longer type position. And in fact, a pro tip here would be. Even as you're looking at these companies, think a little bit less about the specific role that you enter in on. Think about it as it's a multiple role journey. So, let's say you were to go join a Microsoft, my gut tells me you pick a role where you think you can succeed in your first one to two years.

Expectations are below, maybe what your own is, you feel like you have chemistry with the team. You feel like you can pick up the product fairly quickly. Maybe it's something that you have domain experience in, or maybe it's a technical area that you've had depth in, or maybe it's a set of people that you've supported in the past or that you've appeared with in the past.

And you're like, hey, my first 1 or 2 years is going to be pretty solid. I don't know if I'll make my mark though here. Maybe this thing's not growing exponentially. Maybe this is not the, hottest project within the company. But then, you know, 1 to 2 years later, you're inside the tent. You know, you understand the culture you've made relationships, your engineering lead moves to another project.

They say, hey, you know, this would be a good one for you to take a look at and that's where you really make your mark. And that gives you this sort of 4 or 5 year tenure. And I just like that story a lot more. And so then the art of your search is go pretty broad on these big tech environments, but really isolate down on what role you can actually exceed expectations and have a solid 1 to 2 year and, you know, leverage a superpower, as I mentioned, domain, relationship, potentially a logistic situation where it's like, hey, this happens to be in my backyard. Those types of things help you kind of narrow in on the big tech type position. So I'll pause for a second to see if you're tracking and any thoughts or comments on that.

Guest: Yeah, it's helpful to hear and it's validating I feel like I've come from a part of tech where I've trained myself to feel like going to the scale companies isn't cool and isn't a great thing to have on your resume. And so there's this very surface level bias toward thinking, well, if I'm going to go there, then I need to be able to justify it by taking some incredibly innovative or high leverage role that makes it look and feel better about being at one of those companies.

But on the flip side, my intuition has been that it's not realistic to jump directly into whatever the hottest thing is, and that it does take time to navigate these companies and that I probably need to start with being a little bit more open. I think what I would be most concerned about is if these companies are in a place where even internal movement is tough and going to continue to be tough.

Do I accidentally end up in a place where I dead end in a role that's not particularly compelling? That's maybe like the downside risk in my mind, but my gut has been telling me that's less important to focus on than just finding the right fit and a role that works and kind of going from there.

Nikhyl: Yeah. I mean, if we go through some of the risks, that's not the risk as you point out that I would kind of pull forward. My sense is that the data shows that you're almost certainly going to see massive career addition. For having one of the larger tech companies on your background, especially if you've had impact there.

If you look at almost all the senior top product executives in the industry, I think over 90 percent of them have done a tour duty at some very established company. And I think that the criticism, if you said to me, hey, I'd really like to get an elite role as a number one in my industry, what I would say is, well, you haven't seen the movie.

You haven't seen what it's like to be in this sort of leadership role. It's something that was really working at the scale that the company desires to obtain. And so what you gain by going to the Microsofts of the world is you're like, yeah, I understand how product management is done at this stage.

I understand how they can deliver multiple products at the same time. I understand how they can take a culture that is scaled and drive innovation, and these are hugely valuable things. So I think the optics of having a tour of duty of this type of company is hugely valuable. I think that the more likely risk, if we take the flip side, is that you just feel like a cog in the wheel.

You know, there are thousands of people that are in your group. There's a very tightly held way of how product management is done. It tends to be built over decades of experience, and so you are not trying to change them. They are trying to change you. I think that that's a huge learning opportunity for those that are curious, but you might end up becoming a product manager that you do not desire to be. You know, when I joined Meta, for example, Meta tends to be very data driven, very growth oriented, and it's a very complex system. So I had to kind of put my thinking cap on in a way that I was tending to be as a consumer PM, much more intuitive based, this tends to be more data based. This requires a new skill for me as well as a new understanding and appreciation for product management.

Some people are like, this is crazy. I don't want to do that. Some people thought this is not my first choice, but I'm curious. And some people thought this is amazing. This is what I've always wanted to be. That's a risk. You could be one of either of these three doors. So, I think that when you get there, it'll be like, wow, there's a lot of things to learn, but then you might feel very unrecognized. Your concern that you made around leadership transparency might be very much on display. You're 17 degrees away from some of the leadership decisions that might impact your role and your project. So these are the things that I would be like more weighing. Now, the last point that you made, which again, I think is very insightful question is, hey, if I feel like I'm in a dead end role, because the roles that are on the website for openings are never going to be the highest quality roles. The highest quality roles are usually the ones that go internal because those are the people that are already in flow. I think that if you look at most tech product leaders that are at big tech, it's pretty normal for them to have multiple stints.

Internal mobility is generally is very much supported. it certainly is the case at Meta certainly is the case at Google. And my suspicion is, it's very much the case at Amazon and Netflix and Microsoft and, you know, all of these other later stage enterprise companies like Salesforce and others.

I suspect that it's encouraged because. You know, when an opening opens up, as I mentioned, you want to go with proven quantities, and there's really no stigma. Now, your manager may not be thrilled to see you leave and you might have to deal with an individual situation, but it's normal. And in fact, in some cases, highly encouraged to move, so that I think is not as much of a concern is just feeling like more lost and forced into a different style of work.

Guest: I come both from companies and roles that are deeply, deeply experimental output metric driven, that's the sort of environment I'm used to operating in where ultimately it comes down to the numbers.

I've spoken to people in larger organizations. I had a conversation with somebody at Google where I was shocked to hear their team has never talked about moving an output metric. One of the things that I'm trying to think through is it sounds like there is daylight between scale companies and how they operate in that way. And maybe Facebook is more on the side of the spectrum that I'm more used to.

Does it make more sense for me to go to the sort of organization that's kind of the what I know, what I thrive in, and what I think I would naturally be much better at? Or does it make more sense to try to push myself into probably the most different culture that would probably feel pretty uncomfortable to me for at least some amount of time.

Nikhyl: I have such a good question and I really love the framing of it. I think that there's sort of two elements to what you're discussing here. One is that if you look at the spectrum between intuition based product management and more data driven based product management, you find yourself placed closer to the data Is there value in trying to walk the other path? And are there big tech companies that tend to sort of gravitate towards the left versus the right? My sense is that given the climate we're in, I would definitely not venture into the intuition based product management discipline. especially as you head towards big tech, you want to be in a position where you're either scaling a successful product or expanding a successful product that already has distribution.

There's plenty of those examples. But I think that your comment around, hey, I talked to someone at Google or a product team at Google, and they tended to be a little bit more intuition based. My sense is that the question really comes down to how much is there to lose for that team as they build new product?

If you go talk to the search and ads team at Google, they are going to have a lot to lose. They are not going to come up with new concepts, throw it out there and hope it sticks. They're going to, you know, measure 77 times and cut once. So they have a lot to lose and their small gains turn out to be relatively sizable in terms of impact.

So I think that the core products within any of these late stage companies tend to be much closer to this data driven system, product management type innovation. Now, the very more speculative parts of those big companies, they tend to have less to lose and more to gain by being more quick on making decisions and heading in a direction.

Most of those directions that people head in tend to be driven by leadership, not driven from the bottom up. So, most of the time, you know, a leader comes in a vice president, or maybe even the founder, the C level executive, and they're like, we want to go in this direction. There's no data to support that and then you're in that mode of sort of supporting that execution.

That might be the exact thing to avoid just given some of the discussion. You don't have as much transparency, the data doesn't support it. You're not as excited. It felt like a little bit of a, we do this for six months and if it doesn't, we just change it, but you're doing it at the speed of a large company, not a small company.

You're like, this seems pretty awful. So I would be like, hey, based on what we're saying, I would say big tech. Yes. Core product. Yes. Yes, on data driven, less intuition, and then really make your mark in that arena, but I would definitely not say Google bad or Meta good. I would just say it's core good.

And you might want to chew on whether it's a Meta, Google and others, do you want to start as an IC and is that okay? And that again comes down to this question around expectations. Can you crush it as an IC and then move to management?

Or is that such a step backwards from ten to three to zero that you're just like, hey, that doesn't seem like it's career additive. It's an open question, but I would probably get in process with most of the big tech companies.

Guest: You touch on a last interesting point. This conversation of people who have been managing moving back into IC roles feels like such a hot topic right now. I know a lot of people who have done it.

It's something that I'm really struggling with. Less so from an optics standpoint, and more so from a, do I think that I'm going to get joy out of the leverage and impact that I can have in an IC role after I've been managing for six years. I don't know what it would feel like to go fully back into an IC role.

Nikhyl: My counsel is if you still have joy in doing IC work. And skill, and being hands on, it is substantially the better route to join a company today. Particularly if you've never worked at late stage, because what you do is you learn the way products are built from the bottom up the more that you become an indirect leader and having to pick up the process, the products, the system, you know, you're trading off depth for scale and scope.

The problem then you need to be able to do is direct folks that have really understood the details. And so if you can delay it by a year or 2, but you really understand something in depth. My guess is your 5 year career is going to be better. If on the other hand, you're trying to optimize for a 1 or 2 year career, it'll look more like a step backwards, and if you're just like, I don't have joy in building things directly as much as I used to, then it'll be a challenge. I do think that this is a big accelerant to your job search if you're willing to do this. I think the accelerant is massive because what it does is essentially it says, hey, this person is willing to be hands on.

And oftentimes people, whether it's in late stage or even growth stage, they're looking for more hands on leaders. So it's sort of a nice marriage. But I think that it's an investment that you'll have to get comfortable with.

Guest: You're the first person who's framed it in terms of the short term versus long term value. I feel like what I mostly hear from people right now is, well, it's really hard to get a management job. And so you might just have to be willing to go into an IC role, or at least a player coach role. But it sounds like your take is that at a big company, you think there's actually compounding value over time and having started as an IC to more deeply understand it before trying to drive impact directly as a manager.

Nikhyl: Kind of connects to my 5 year framework. So if you're going to be at the company for 5 years, if we determine that's your sweet spot, and we decide we're going to take 2 roles to get there, then the question, of course, that we discussed is what's your first, what's your entry role? And my entry role is always the one which has the lowest expectations that you can crush.

And so if you took the management piece off, because it's really hard to crush something when you're indirectly, you know, accountable for something. If instead you're like, hey, I'm going to go and build this thing and I feel really confident that I have maybe the skills because of the superpowers, but it's a hands on role.

Maybe your second role is the management role. It's the promotion role, you know, and it's the role where you have the most of your impact. And the story then is, yeah, those first couple of years I got my acclimation and I really got my sea legs. And to me, that's just a very thoughtful career management.

Plus you're also trend friendly. The markets are in the process of recovering. So growth starts to pick up. You're trusted. You people look at you inside the building and they're like, wow, this person's really crushing it. I think he's a bit over qualified. Let's move him forward. Right? So all of this feels very thoughful.

The only thing that you don't have is it's this sort of optics are not maybe awesome, given your history, and you have to write the docs and get into the details more than maybe you've been in for a while. And some people are like, that's just not who I want to be anymore. But I think that this is probably going to impact your search and this decisioning more than any of the other aspects, because, because it's such a acute issue right now in the industry.

Okay, so as we wrap up, I just wanted to conclude with a few thoughts. I think the most important one is that anytime you're in a job transition, it's important to personalize the search, but also think about stage of company, not just the name of company. I like the way that, the caller really thought through the stage of company that was right for himself, and I thought that that is going to lead to a much better decision. I think that startups are risky, but maybe for slightly different reasons that people think right now they're healthy, but they do require a different compensation structure. I think that quality growth companies are just hard to find.

And I think that having gone through one experience, it didn't quite make sense for him to repeat that versus maybe look and oscillate between stages, find a new opportunity at a very different phase of career. I think that big tech is really attractive right now, but I think you have to have those specific reasons.

I think that these longer tenures are required. You just can't go in with a couple of years in mind. You have to almost have a double jump model where you look at the 1st role as a starter role where you can exceed expectations and then a 2nd role where you really have your better and stronger impact.

I think that you are going to be a bit of a cog in the wheel. And you're not going to have as much transparency on decision making. There is a lot of people that are in the company. So it's very difficult to find your own place, especially if you're used to being in a smaller setting.

And I think that impact is very hard. You find yourself being changed more than your ability to impact an organization. But you do get to witness what a successful organization looks like. Companies all the time are looking to bring in people that have had experience at later stages, because they want to bring some of that experience in because you've seen that successful environment take place.

And then, of course, compensation is liquid and you also get the appreciation of that stock price, because the expectations are very realistic. The market's already set a realistic expectation on the compensation. and lastly, we touched a little bit on this sort of conversation I've been having on the podcast for a few episodes, which is the importance of being hands on and potentially being an IC and how that can actually be a career accelerant versus a headwind on one's career.

And when evaluating big tech companies, it's really important to look at the type of project that you're on, not just the name of the company, because the closer you are to the core, the more data is going to be used. The further you are away, the more intuition is going to be used, because obviously there's less to lose and there is fewer users in those non core businesses than there are in those core businesses.

So, hopefully, you found the conversation useful. Thanks for listening to The Skip and 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 always subscribe to the podcast on Apple, Spotify, YouTube, or wherever you currently listen.

You can also follow my newsletter on Substack and have questions or feedback, or perhaps want to join me for a future call, leave a comment, or send me a note on LinkedIn Threads or Twitter. I try to answer each one directly. As always, I'm Nikhyl and this has been The Skip.