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Ask HN: Fairly successful startup CTO – How to return to a big company?
19 points by thisthingon on March 25, 2019 | hide | past | favorite | 5 comments
Hey all-

I started a mildly successful startup and now going through a mildly successful acquisition (100+ employees, 30+ Prod/Engineers, Series C), and thinking about what comes next. Was hoping to maybe go into one of the FAANG for a while (or something similarly large). Anyone done this? Any suggestions? What jobs do I even apply for?




Sorry to hijack but I’m genuinely curious why you want to go to a big company. I would assume many of us view an acquisition and the ensuing payout precisely as a pathway to set the terms of our careers and NOT have to work for a large co. So you seem to at least be defying expectations.

I’ve been at two of the FAANGs as well as several early stage companies, and my opinion is that a person who enjoys everything that comes with the startup life enough to see one through to an acquisition is likely to find him or herself grossly incompatible with the reality of working at a FAANG company. But I am very curious to hear your rationale.


Not OP, but my 2 cents on this having bounced back and forth a couple of times between a founder and an employee at places.

As a (co)founder life is stressful for quite awhile with a lot of pressure and weight on you. Even going through funding rounds is stressful, getting the money removes certain fears and stressors but raises others, so it isn't free of issues either. Joining a FAANG company allows you to play with some technologies you may not have been able to prior, or to play at a scale you weren't able to reach and add that to your list of skills. And do so at a lower level of stress than starting over as a founder. And sometimes, people find they aren't cut out to do the founder route after doing it so this is their way out.

Basically, to me it is a way to reset yourself while getting paid, learning some new skills and staying relevant while you find your next thing.


I'm curious; were you an employee at the startups or a founder? The experience (and stress levels) will vary quite a bit between the two (and I'm not saying startup employees have it easy by any stretch).

I can definitely see someone who has been in a founder role for years wanting to trade that for the stability, predictability and low-risk environment of a FAANG for a while, especially if they have a family, kids, etc.

Although a few exceptional people can do both, most founders sacrifice elements of their personal lives in order to put enough energy into their businesses. A "successful" founder can be a failure at home. It's not that you're absent, but you're also not the best partner/parent/friend that you can be during those periods. A stable, "boring" job can be an opportunity to dedicate more to those important things.


This is a pretty common post-startup experience. You'll likely find that positions in the Senior Manager to Director/Senior Director range are a good fit. It's often easiest for hands-on CTOs to transition to Director of Engineering roles but look at Product Director and VP of Product roles also.

The most likely challenge if you haven't been in large enterprise before is that the level of formality around processes and permissions can be a hard-start for people accustomed to the speed and autonomy of a startup.


Startup experience is probably about as valuable as a Master's. Which is to say, it varies a lot. Sometimes it might be less valuable than working for that period of time. Sometimes it makes you unique and stand out.

I wanted to go to a large company because it was the only route I hadn't taken by then (and my wife kept bugging me not to gamble with startups and give it a shot).

If you've done startups even fairly well, large corporations feel frustratingly slow and incompetent. I'm not sure if this is the case with FAANG, but Google and Facebook have hardly created anything new. For engineering roles, you'll also have to go through the coding gauntlet, spend months revising algorithms that you'll never use. This is not necessarily a bad thing if you have time and want to skill up.

Another option is investing in new startups. Depending how big a deal you got, you might be of angel level and have better than average odds. You could probably make good money as a full time investor on NASDAQ, or work with a VC.

One thing I did enjoy is teaching. It might not pay so well, but it's fun to impart your skill onto others. You sound like you're at the level where you can also give advice to established groups like 500 Startups, though not necessarily on a full time basis.

Also one of the best times I had was consulting for large corporations. You're at the stage where you're practically a superhero to some. It pays well, and you also get some of the perks and feel of big corp like work, like wearing a tie and nice food.




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