
Ask HN: I am at a startup for 7 years. What's next for me? - firstemployee
I was the first employee hired as developer for my current startup. I have been working with them for 7 years now.<p>We have had multiple funding rounds. We grew and downsized multiple times. Had big quarters and some really shitty ones. I have survived all the ups and down. Currently I am leading the engineering team. I do have some shares but there is little chance of a big exit so I am not expecting a huge payout in the end.<p>Like any first employee I&#x27;ve wore multiple hats. From fixing stupid little bugs at midnight to setting up processes for dev, hiring, code reviews, qa etc.<p>My biggest concern here is that due to my role I am neither an expert engineer nor a good manager. I am just sitting in between focusing on whatever the company needs at the time. I feel I could be a really good resource for another startup but I don&#x27;t want to go through this grind again. And for big companies I don&#x27;t have the expertise to either pursue an engineering role or managerial role.<p>Did anyone go through a similar experience? What do you suggest my next steps should be?
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deanmoriarty
I have a very similar story to yours, and haven’t been able to get excited
again about a role.

I also was the first engineer of a startup, grew to technical leadership and
jack of all trades (infrastructure, developer, manager, architecture, hiring,
technical sale, technical support, product, public speaking at conferences,
...), and moved on after 7 years.

The next two companies have been a disaster, I took a role as IC and then as
manager, but was miserable in both positions. Too structured. And my
experience was too wide. I like to tinker with everything, I don’t have the
desire to study the minutiae required to perfectly code a complicated C++
template, and to iterate over a code review until it’s the most esthetically
pleasing piece of code. I like to think about the entire system and the
business impact.

I’m thinking about trying a PM role, or also a customer facing technical role
as sales engineer, since I have played all those in my past.

Like you, I don’t want to work at another startup because I basically burned
out, startup life is hard at 70+ hours a week.

I was lucky that my equity turned out to be slightly valuable (slightly more
than $1M USD before taxes, so nothing too crazy but better than a punch in the
face) so that affords me some freedom since I already had a high savings rate
and frugal lifestyle. It’s been much easier to have enough savings to be able
to leave when you are unhappy.

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dmarlow
> I like to tinker with everything,... I like to think about the entire system
> and the business impact.

This sounds like me. I am still at a startup since early on and now I mostly
focus on one thing. I now get extra time to devote to my passions and doing
things "my way".

There should really be a group chat for first/early folks. I feel we take on
significant risks that don't come with the correctly adjusted rewards.

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nulladdr
So you've led an engineering team and been involved in every part of the
development process. You built a product/service from scratch and grew an
engineering team from the ground up. You defined development processes to help
the team deliver high quality software. You focus your energy on whatever the
highest priority is for the company and likely spend a lot of time helping
your team members move past obstacles. You probably don't do as much coding
anymore, because that is the least useful way to spend your time and expertise
when you're juggling these other responsibilities. This lack of coding might
feel a little weird if you still consider yourself a developer, but your work
has a force multiplying effect across the entire team. You described this as
sitting in between an engineer and a manager.

If I got that right, you have just described a "tech lead" role, and your
experience is far more valuable than a standard developer role. You can find
those roles at companies big and small, depending on your preference. They're
easier to find through your network than through job postings. They carry a
lot of responsibility, but they can also be highly rewarding.

You're the only one who can decide what you WANT to do with that experience
though. Do you want to find another tech lead role? Update your resume to
emphasize your leadership experience and technical background. Development
role? Emphasize those aspects of your job and start grinding on leetcode.
Manager role? Emphasize your leadership experience and how you helped grow the
team. You're well positioned to move into any of these roles, depending on
what you want from your next job.

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bilbopotter
Don't undersell yourself. You are leading the engineering team. To be clear
management is not rocket science

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giantg2
This.

And I hate this term, but the concept is real - "Fake it until you make it".

~~~
weitzj
Ant don’t grow bitter in your current situation. Make a decision

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muzani
It sounds like you're in a good position. Maybe you should try to be either an
expert engineer or manager. These things take effort. If your company won't
sponsor training, you might have to pick it up yourself.

The question arises why it's still a startup. Is it lacking leadership? Poor
luck? Weak market? Since you've already put on so many hats, maybe take on
another and try to fix that.

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weitzj
My guess is you are totally fine with your experience, to pursue an
engineering role.

You have worn many hats. Therefore in a big organization you have the ability
to develop yourself in many directions.

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jameshush
It sounds like we're in similar age ranges. I've done the startup game
(employee 11 at a per-series A sleeping on the floor next to the CTO) and I've
done the big company life (more stable, but can be slow at times).

What do you want to do?

If you want to code, deal with an average amount of politics, and focus on a
more predictable cash flow and career path, start drilling leetcode.com, set
up 10 interviews with the top 10 tech companies, fail 7 and get 3 offers.
It'll take about 6 months. There's plenty of "normal" work at FAANGs, not
everyone is Machine Learning things together there. With seven years of
experience getting the interviews will be very doable, passing them will be a
bit tricky but doable after you get into the groove of things.

If you want to focus more on managing you're already doing great. If you want
to increase your income start applying to other manager/director roles and get
a competing offer. The formula of "Do 10 interviews and fail 7" works great
here too.

Do you want to start your own company? Teaming up with a friend who has sales
relationships or strong marketing experience to get users could be fun.

Not sure what to do? Take some night school classes. I took an eight week
product management course just to see what it was like. Turns out it wasn't
really for me. I took an online software engineering prep course too to
prepare for the bigger company interviews, I wasn't a huge fan either.

For me personally, I realized I wanted to be more customer facing so I'm
working on switching to a more sales focused path. Once I figured out my
destination I've worked backwards and figured out a path to get there.

You can't lose. You're doing great now, just figure out what you want to do
and work your way backwards :)

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donmb
You have the exact same history I do, except I am working in the startup for 5
years, not 7. I will found my own thing in 2 months with 2 really talented
people with sales and marketing background. I look so forward to do my own
thing, making my own decisions etc. Good luck to you.

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plasma
My first suggestion would be for you to dust off your LinkedIn profile, make
sure its thorough in your responsibilities (and how many hats/experience you
have).

You should find some (more) recruiters start to knock and that may start to
bring you some new opportunities for perspective.

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agustif
Bootstrap something you want to exist?

Being your own boss brings a lot of freedom of choice.

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exdsq
You sound like a solid CTO for a scale up - you’ve seen it all, writing good
python is a lot less important in the long run

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phanindra_veera
Why dont you try to be an entrepreneur ?

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bruceb
Well he worked for 7 years at a startup and it didnt workout That well.
Founding somthing is hard and most likely you will fail. There is that.

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phanindra_veera
May be he can try to bootstrap it himself. Something like an indiehacker.

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op00to
Product manager?

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john4534243
> I was the first employee

Remember that you are an employee unless you have any equity or something more
than a normal employee. If you dont just dont sweat, focus on building
skillset and move on. IF you don't have the time in your current organization
just quit and focus on building your skill. I can't stress this enough.

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ckdarby
> I do have some shares

Please read the full post before commenting.

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Twixes
Supposedly this equity hardly matters to OP at this point

