Ask HN: Moving from a startup to a big co, what should I be aware of?

180 points by 1729 ↗ HN
To add more context to my question, I’m currently in a product leadership position at a ~300 person SaaS company and I found my way here by way of a semi-decent exit as part of a startup’s founding team. However, I have been considering a switch to a much bigger company (Microsoft, Google, AWS) of late. All I’ve ever learnt over the last decade has been by operating in a capital constrained environment. Moreover, I don’t have a lot of reserve energy in the tank to direct it at another startup after 10 years of blood, sweat and toil.

I often find myself thinking of and seeking out experiences from my peers at these behemoths on how decisions are made and products get built there. On one hand, I’m scared of slowly going further away from all my learnings as an entrepreneur (a lot of which haven’t come easy!!!) but on the other I feel like not having had relevant experience in the right BU/product within a big co is limiting my field of vision. What are some things I should consider before switching?

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Having gone the other way, from Microsoft to entrepreneurship, I would say you are better positioned for success. For the most part your skill sets will transfer over to product management in a large company fairly easily. Some things are different though. You will typically be responsible for either part of a product or one product in a portfolio. As such your product or feature's future depends not just on how it is doing in the marketplace, but how it does relative to other products and features in the the portfolio. So you need to work with your managers to evangelize and promote the product within the larger organization as well. You'll have be able to justify its existence, very robustly with a lot of data. Much of the mid-level product managers function within a large company comprises of this activity. This may seem wasteful to you, coming from a startup, where the verdict of the market was everything, but this is how large companies determine how resources are allocated. Eventually the market will determine the future of the product, but for many product managers in large companies, that success or failure will not occur in the duration of their tenure. So one thing you need to focus on a lot is networking with the internal power structures of the company to build support for your self and your team. You have a huge advantage in this respect as an acquisition. They have paid good money to bring your team in, so there is significant awareness of who you are. If you are careful, and politically savvy you can leverage that awareness, and initial goodwill into strong long term support for your team and product.
You will probably have less freedom, less authority, and more bureaucracy.

You might have a leg up when it comes to keeping your budget low. Upper management is always happy with that.

I once worked at a Fortune 50 company where keeping your budget low was something that upper management (at a certain level) was not happy with. We once built a hadoop cluster because we needed to "burn" some money (~$150k) left in our budget. In this company coming in under budget meant you didn't do a good job of forecasting your needs so you were punished with budget cuts the following year. That led to so much waste. Coming from a startup where saving a few hundred dollars/months was something to celebrate it was mind-boggling to see all of the waste.
From your context description it sounds like you need some extended holidays to put things in perspective.

For me, the biggest difference is that processes in a big co are designed for any single individual to be replaceable. As a consequence, everything is bigger than you and slower to change even if for the best. This is exactly what you're trying to achieve in a successful start-up as it starts with everyone being irreplaceable (to some extent) where you can make a fundamental difference in the future of the company.

Being part of a successful company sounds exciting and you can learn valuable information to apply in other settings but I found that in start-ups you have a lot more room to learn than in a big co. This is because instability in a start-up is very visible and directly accessible (you'll run out of money in X months) so you must timebox everything. However, in a big co instability is more implicit and you can't fail as much. Also unless you can get a fairly high level position at a big co, you won't be able to get "very" relevant experience into building/working the right product because a lot of strategy is not discussed bottom-up in those companies.

Here is what it means to work at a big company:

* Things work slowly, so relax. There are many people that have a hand in every aspect of a product decision.

* At a startup you are actively changing the world. That’s done now. Put that completely out of your head. You are cog in a machine. Instead focus on your assigned product, help your teammates, and just learn to relax.

* You, the individual, are not important. The product is important, the department that delivers the product is less important, the teams that comprise the department are less important than that, and so on. Again, accept the reality and just relax.

* Do your best. Unlike at a startup, generally you will have time to get things correct. This is the difference between competence and others who struggle to get things right and always appear to be in a hurry. There is no reason to be in a hurry.

* Expect insufficient test automation, lots of regression, and plenty of repetition. Also expect everybody to be an expert that is in a hurry and things in a unique way. Just be patient, politely nod, and just relax.

* If you are good at systems automation then learn to automate away as much of your job as you can. Use the now increased free time to contribute to documentation and internal knowledge repositories. You will find that a lot of the documentation can be automated as well.

* My employer has something like 270,000 employees so it’s forgiven if you have no idea what all of those people in your cubicle farm do. You need to actively spend at least 2 days a month answering those questions.

* Just because you are at a big company does not mean you are safe. I have been in a large established super well known .com that failed. People get laid off even when big companies are healthy.

* If you don’t like being bored and are highly risk adverse you might find the big company life highly depressing. A lot of my advice here is to just relax, but I hate relaxing.

Can't agree to this more. And depending on the size of the company, it might not be just few weeks, things which you would think should have been done in a month might take up to a year. And meanwhile everyone WILL keep talking about moving fast.

People will keep coming in and going out and you would end up have the same conversation with many people many times. And everyone will try to suggest "one change" at a time.

And there is nothing wrong with all this. This is just how big companies work, you cant fast-forward any of it.

This is all fantastic advice. I spent the first 26 years of my career working at startups and small companies before taking a job at a big, public tech company last year. This advice is spot-on.

I find that I'm actually working much harder here but my work is more focused and in a single lane. I'm not bouncing around all day between 20 different things. I'm grinding for months on end on one tough, big problem. It's not bad, just...different. The pay is much better here but you are expected to _be_ better.

This all sounds perfect!

At {current_job} it feels like I'm slowly developing faux-ADHD from the "priority 1" task changing, often, multiple times a day. Personal projects are a bit of a respite from it, since I get to focus on the one clear, long-term task for good stretches at a time, but recently I've been too burnt out to do even _more_ programming after yet another hectic day.

I feel like I'm a competent SWE, but the nature of the work means everything is a ticking time bomb. If you're rushing all the time, code quality, testing, and all sorts of other sanity-restoring factors become a distant dream. I'd love to take ownership of a few aspect of a large system and slowly improve whatever I can. But the grass is always greener on the other side, so I'm sure this would come with plenty of negatives too. For one thing I feel like I'm too early into my career to be acting as a faux-CTO and being the go-to for all big tech decisions, infrastructure, etc, as well.

Would you say there is an inflection point at which startups stop being like this? 20, 50, 100, 500 engineers? More?

Sorry for the ramble!

At the beginning of a startup, there are no "big tech decisions" per se, only a whittling down of your problem space and target market. If that can be done with zero technology, all the better.

What gets to be called a "startup" is highly debatable, as some billion-dollar companies have still been called "startups". However, you will only get to be faux-CTO if you get in really early, or start one yourself. Best of luck!

* Things work slowly, so relax.

The extent of this is hard to grasp outside of bigco. At oracle we had layoffs/reorg - no real work was done for ~7 days, and it took 3 months to figure out our new roles/responsibilities. Some people were paid $40k+ in that time period and did very little work.

Things occasionally move very very slow. Twiddle your thumbs and be happy about your huge salary, don't quit like I did!

Seriously. I heard big companies were slow before but I didn’t realize the magnitude of it until I joined one. Most people where I work either only produce real work for anywhere between 40 to 10% of their time. The rest is either filled by busywork or twiddling your thumbs (depending on individuals)
Or meetings, meetings, and... more meetings!

My 2 cents:

As a contractor, charge a lot. They either have budget and want to spend it RIGHT NOW or they don't. The manager engaging you doesn't really care about your daily rate (relatively speaking).

Above comments on automation is spot on. Test suites might be terrible, so the care required to make changes without breaking things is your responsibility, hence the slow pace. What is in your control is the ability to automate your own testing.

Integration with poorly defined APIs is an important skill. You generally won't have another team maintaining and improving a nice API. You will have access to obscure data stores dumped untransformed in the data warehouse from another megacorp's expensive and poorly documented product, possibly with myriad ETL nuances (read: bugs). Learn to work with this and you can extract gold.

If you have a Windows SOE system, embrace Cygwin/similar.

> Learn to work with this and you can extract gold.

Curious if you have any tips for this stuff? My instinct would be to just poke and prod things, writing tests or documenting things as I go along. "I wonder what happens when I do X" -> write a test, get a result. "I wonder what data looks like here" -> examine it, write a summary of what I found. Etc.

I have been a contractor/consultant for the last 7 years. What I've seen when you try and go down that "write a test" path is. Oh there's a 2500 line stored procedure with hardcoded network paths for production data in it. Or, this api only runs on the 2nd Tuesday of the Month but only after 8pm when the day of the month is also even. There's so much do-it-live embedded in the legacy systems it takes months to make enough seams to even test things in isolation outside of production. But, if you can get buy-in to make those changes, then exactly what you are talking about helps a ton.
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Love being a contractor. I'm currently unemployed but gave multiple years of savings.
It's such a nice feeling to be inbetween contracts and not have to worry about how you're going to pay bills. I feel like I've only just now gotten to that with my business. Congrats and hopefully not unemployed for too long (unless thats what you want!)
The last 6 months I worked at a large for profit education company all I ever worked on or "released" were simple configuration changes. it was a struggle to find things to fill my day with.
They say "Oracle is where startups go to die" for a reason.
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> A lot of my advice here is to just relax, but I hate relaxing.

Hit the nail on the head with that one.

I came from multiple startups to a FANG and this advice is really good. Seriously, you’re going to need to relax.

Also I recommend reading “corporate confidential”. I was confused initially why being an excellent engineer who could “deliver” didn’t make me shine at bigco. The book helped me get on a better path.

Also relax.

I found 3 corporate confidential books on Amazon: by Susan Dephillips, by Barath Surendran and by Cynthia Shapiro. Which one do you recommend?
You want the Susan Dephillips one. Very eye opening, if you've never worked in a big corporation before.
Thanks. I have actually for many years and up to 150k head count, but never learned to properly deal with it. Moved onto a mid-sized company which is growing into a conglomerate of its own. I did like Erik Dietrich's Developer Hegemony, but his style of dealing with big co felt a bit too cynical.

https://leanpub.com/developerhegemony

Why would I find it depressing if I’m risk averse? You sound like the only risk is getting fired for a random reason, which could also happen at a smaller corp.
I am so used to using the phrase risk adverse because is the more common phrase in my military side job. In the real world the common phrase is risk averse.

The first means a personality type that doesn’t perform risk analysis normally or does but simply disregards high risk concerns. For example it doesn’t make sense to jump out of an airplane or leap into combat. There is a preference for people who can weigh those risks and override the common sense factor that results in terror. In the business world this could mean investing your life savings into a start up idea knowing you might likely fail with nothing to show for it.

The second more common phrase refers to opposite personality types that cannot proceed in the face of uncertainty. These people are terrified to make a decision where the outcomes are unclear and thus hesitate waiting for increased certainty or for someone else to make that decision.

https://en.m.wikipedia.org/wiki/Risk_aversion_(psychology)

My personal approach to these terms is to simply make a damn decision even with insufficient evidence, because then you are at least doing something. If you later discover your decision is wrong then simply shift direction in the face of new evidence. People who sit there waiting for clarity, feels like an eternity in hell, makes me sad.

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> At a startup you are actively changing the world.

That sounds very exciting. Can you point to one startup that's changing the world?

SpaceX?
SpaceX was founded almost 20 years ago and has 8,000 employees. That is not a startup (today) by any reasonable definition.
Are they though? They're almost 18 years old at this point, so I feel like they don't really count as a startup.
How old and how large has really nothing to do with being a startup or not . It just means a fledgling business whose revenues are expected to change rapidly and is developing a product/ business .

This is in contrast to stable or blue chip like companies who have stable revenues and their product lines are very well established.

The distinction is important for two groups of people .

a) investors - Risks and rewards are fundamentally different , therefore valuation methods are also different t you would use something like a Discounted Cash flow for stable corp you might look at IP, ARR , DAU or any number of other metrics for a startup whose revenues are not stable enough to use DCF etc

b) employees - change or innovation is far more deeply grained culture in startups , What worked yesterday may not work today, that requires different mindset to be successful at

Amazon , Uber are still startups despite what you think about their sizes , ages and current revenues . Building a AWS is only possible if you can completely rethink what is that you sell .

I didn't take that literally - rather that at a startup, most of what you do has an immediate and obvious impact on the company.
Something tells me this question is not asked in good faith.
There are legit startups out there that do change the world. Most of them are not companies that you've ever heard of.

I think that companies that change the world satisfy the following criteria: 1 - their work is very hard to replicate. Not impossible, but it would take a competitor a long time to reproduce their product or service. 2 - people would notice a tangible impact on their life if the company disappeared tomorrow.

We won't know which small startups right now are and aren't until several years from now.

All of the big cos right now that have changed the world were a startup not long ago. Yes, not all of the startups will succeed, but there will be yet another trillion dollar company some day which is today somewhere in the realm of early stage startups.

Some counter experiences, just based on my own annecdata.

> * You, the individual, are not important. The product is important, the department that delivers the product is less important, the teams that comprise the department are less important than that, and so on. Again, accept the reality and just relax.

Working at startups I have never felt less important as an individual. The product is #1 and I only exist as a cog in the machine to produce that product and make the founders money. In a big company I was encouraged to pursue professional development, my professional goals and dreams were catered for and I felt like I could make personal progression.

> * Expect insufficient test automation, lots of regression, and plenty of repetition. Also expect everybody to be an expert that is in a hurry and things in a unique way. Just be patient, politely nod, and just relax.

Again, opposite experience, startups don't have time for test automation whereas big companies generally do.

> * If you don’t like being bored and are highly risk adverse you might find the big company life highly depressing.

I'm often bored at my startup though never lacking for work. It's just that the work can often be monotonous work because the startup doesn't have time to automate it or hire someone to do it. At a startup, its rare that you're encouraged to explore something new that might not work out. There's just not the time or budget.

Maybe it's that employees are some sort of cog about everywhere and test automation is also bad almost everywhere.
Truest comment here. I’m co-founder at tesults.com and the biggest reason we discovered for dropping off the product is because upon integrating they realize their test automation is in such a bad state there’s no need for the service :-) It’s a shame because regression is commonplace. I wrote about why I think it’s done badly on the blog (https://www.tesults.com/blog?id=why-automated-test-projects-...)

I’ve worked at companies with 100k workers down to 10 people companies and the employee is generally a cog everywhere unfortunately but you learn different things. I started out in big companies and learned nothing about the business side of things whatsoever in those years. I did learn solid technical skills and practices though. I think smaller companies are the way to go if you intend to do your own thing one day. Bigger is better earlier in the career to learn technical skills or later on if you need a comfortable/well paying job when raising kids for stability.

I think what you are describing are startups past the early stage. It's the worst of both worlds IMO.
>was encouraged to pursue professional development, my professional goals and dreams were catered for and I felt like I could make personal progression.

I think this is because instead of giving a pay raise, they offer these benefits.

It costs the company nothing.

I had the same experience and the comment about relaxing resonates with me.

Coming from the startup to the big company I could not understand why people leave the office at 5pm. There would be another few hours to work.

Also lots of meetings.

As the previous commenter said. Relax.

I guess you will have a broad skill set from your background and actually in big Corp the nice thing is that with this broad skill set That you can engage in so many different projects. And it is tempting to do so. But you only have this much time a day, and it will not be easy to accelerate your pace. This frustration can be bad for your mental health.

So my advice is relax. But also don’t forget the thoughts you had when joining the big company in the first months. Maybe keep a journal. Because you probably had good ideas but might get overwhelmed by the complexity of the big Corp.

If you have not read the “Accelerate” book, I would recommend this as well.

Also you can observe Conway’s Law in its beauty.

It's worth noting that there is a culture change in some big companies where small teams given more latitude and budget to explore innovative solution (I know because these are the teams I mostly sell to). Also Intrapreneurship is a thing too. Way better place to be in than a medium sized mono product startup to be in if you ask me.
"just relax" good advice.
Well that all sounds terribly depressing.
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I feel this paints a far uglier picture than reality. In my limited experience (been with two fortune 500 companies, one of then in the top 10), you can expect maybe one of these issues(or two if you're really unlucky).
The biggest thing is that you don't really know anything.

_You weren't in the room when the decisions were made and there is oil tanker momentum based on those decisions.

_You don't have a clue as to who is who. People within the organization know each other in non-obvious ways. There is an invisible informal network built of many years, organizational structures, and projects.

_You don't know which project is whose baby. Two equivalent approaches are not equivalent when one has backing and the other relies on natural selection.

None of these is bad. It's just the nature of blindly encountering an elephant. Good luck.

There are systems and processes for everything. The plus of that is that there's a lot less winging it, and that you can just hand a bunch of stuff off to people that know how to do it. The minus is that you have to learn who those people are and how to activate them, and it can take longer than just doing it yourself.
I find a lot of these things you can expect, are just symptoms of an inefficient company. I wonder if there is a big company out there that moves quicker and cares about their individual employees more?
Work is not everything, learn rest of "political" skills if you are not good at them, like presentation, speaking, writing.

Most big corps have done really smart people, don't be afraid to actively seek to learn from them.

This is good advice, these are all areas where I have improved.
Having gone through a similar experience, I would say that your experience may vary depending on org culture, sub-culture within individual teams, and the traits of your manager. That said, there are always loose ends that will need ownership and that's where your "entrepreneurial" chops would kick in. You approach to execution would/should reflect on the lessons you've learnt.

Startup - Enterprise does not mean a paradigm shift in everything. Yes, there are some aspects that would change. And then there will be a lot of scope for applying your self-made learning and leanings.

>Moreover, I don’t have a lot of reserve energy in the tank to direct it at another startup after 10 years of blood, sweat and toil.

>...What are some things I should consider before switching?

Take a break if you can afford it. I think that will serve you better than almost any other thing you can do, work related. I've felt this way, and took a few months off, I was champing at the bit to get back to work and start making something happen. You'll think a lot clearer about what you want to do next with some time away.

After you get out of a serious relationship, you need time to heal, regroup, re-find yourself, re-learn who you are, etc before you start dating again. It's similar with jobs you put a lot into.

I hard agree. Startups can burn you out a lot. I've been there myself. The best position is if you can line up a start date a month or two after quitting.
Well my journey was a bit different than yours. I was Lead Dev at a small startup (<10 people) and went to a non-FAANG Fortune 500 and assumed a Sr role on a team. Things I didn't think would bother were a dress code. It does, it does bother me. Especially in the Summer. I was surprised on my first day that I didn't get to choose my own O.S. I really miss Linux, it really effects my productivity being in Mac. I thought projects Jira tasks would be better planned, they are not, they barely have any information in them. Documentation is a joke somehow. Onboarding was a joke. They just kinda stuck me in there. I couldn't believe I had better processes in place at the startup. Things move slow. Some days I barely have any work, its not much fun. There are things that can't be beat though. Chance to move around. Better benefits. With that said, I'll be looking for a smaller company after I've reached my year mark (they have me in relocation expense cuffs).

I hope your experience is better. If you're going to a FAANG I imagine it will be. This place is much more buttoned up.

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This rings a bell for me. Before I started at a big firm I assumed they'd be super optimised to get people going fast, as its a common occurrence for them. What I didn't realise was that you sitting waiting for equipment and logins for 2 weeks doesn't show up on anyones spreadsheet so its not a real loss as far as they're concerned.

Plenty of time for self improvement though if you're just using it as a stepping stone.

Again I've never had less motivation at a job in my life. And yeah, no computer and no licenses waiting for me.
It’s all about trade offs. You will have a tremendous amount of leverage at a big co. Customers who would otherwise not give you the time of the day at a startup will be happy to talk to you. Take advantage of this and learn from them.

On the other hand you will also have to pay taxes at a big co. Big co got that way in many cases because they have an integrated solution for customers. Integration is expensive but worth it. It takes a lot of people to be in alignment to make integration work. And that takes time; you need to be patient and look for opportunities to make a difference.

"Corporate Confidential" by Cynthia Shapiro is an excellent book in explaining the various motivations stakeholders at a large company may or may not have.

Although the book can be considered bleak, the point is not to train you to suspect your employer, but rather point out various possibilities of politics and power play that may be going on under the surface that are not so obvious from the get go. I.e. it's a survival manual of sorts to a new and sometimes semi-hostile environment.

Expect some resistance for very productive and crazy ideas
I just left Google, for facebook about 3 months ago. In case you are interested in comparison, i can help.
Do executives at Facebook rape less people?
If you end up in a 'bad' company you may make these experiences:

- there are feuds between companies or even departments in the same org

- decisions are not based on facts but on political circumstances

- the outcome of an analysis is often predetermined

- not the best idea/project/etc. win's but the one with the best connections

- decisions are made that are damaging to the company just to deny someone else in the org a success

"You are welcome to visit anytime to provide input on how we can improve our improvements-processes."

and

"Everyone got heard."

This can be true at companies of any size. Sadly.
Bias. A huge deal in these corporates. You’re going to have to either learn how to navigate it or to live with it.

On the other hand, you will get a ton of exposure learning from others and knowing more people. That’s always there for sure at large organizations. Above all, a sense of being a part of a cult.

> I find myself seeking out experiences from peers at these behemoths on how decisions are made and products get built there.

I think you will be mostly astounded at the lack of things you can learn from the way decisions are made inside big companies. Which is to say, they aren’t super rational organizations.

As a multiple FAANG alumni, I can tell you that decisions made are often strongly influenced by politics, individual executive “hunches,” and legacy tech concerns instead of raw cost/benefit or actual data.

The fact is, you’re going to make a lot more money doing much less work at FAANG.

However, very little of what you learn about how the organization runs will be valuable outside of the big organization itself.

Here is my list.

* Things work a lot more slowly in big co's.

* There's a lot more ego involved so prepare for a lot of ass lickers(I really can't think of a better term).

* A lot of "meetings", "discussions", "planning" and so on, which often are just means to kick a can down the road.

* More time to relax.

* Nearly impossible to change the status quo, not impossible but a very slow and painful process.

* Often more freedom to experiment with technologies and proprietary solutions if you find a way to justify them(which is often not a difficult task).

* Plenty of ways to squeeze out training, seminars, certifications and whatnot, just make sure you read the tiny font at the bottom.

> All I’ve ever learnt over the last decade has been by > operating in a capital constrained environment.

Even in big companies you will be constrained by budgets, and possibly even more than you're used to. The big companies have money to try many different things, but normally products start small, and can be killed if they're not going to be profitable enough. Especially if you're ina leadership position, you're going to have to convince people to fund your products.

The other big thing to consider is politics. Don't get me wrong, politics are everywhere, even in startups, but there's a difference. You're going to have arguments with people that you can't go have a beer with after work, and you have to consider how that will affect your relationship after the argument.

Politics.

You better brush up on your social engineering, learn when to smile and when not to, and watch your back. Rationality and intelligence will not get you far on their own, because the game isn't about who's the smartest or who has the best ideas, it's about leverage, prejudices, cliques, "prestige", and ultimately money.

Remember you're there to play with some toys, occasionally commit code, and get that sweet money.

I personally think that one should always look behind from where they are coming and focus on tomorrow. This will help them achieve their goals, both short terms, and long terms.
300 is already pretty big. I went from 20 years where by far my largest company was 16 people, to Microsoft, and I'm pretty happy.

The biggest transition for me was the amount of cross org digging and asking and such required. So much is constantly in Flux, and internal integration points are often poorly documented or have apis based off protocols from a decade ago, or whatever else. You spend most of your time doing that, figuring out how to integrate with various old, half supported systems, getting pushback that the integration won't be supportable, etc.

This is in strong contrast with a small company where you are generally working with public, well documented tools, and everyone you work with shares the same goal.

That said, I'm happy now that I have gotten used to it. The scale of things you work on is much greater.

One thing I'll say is don't sell yourself short by taking a job at the low end of where you think you should be and telling yourself that you can work your way up. I made this mistake when I was unemployed but not desperate. Your project could be canceled or there can be blockers or reorgs or whatever else that keeps you back. So wait for the offer that you want.