Ask HN: I am at a startup for 7 years. What's next for me?

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.

> 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.

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.

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

This.

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

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

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.

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.

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 :)

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.

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.

Bootstrap something you want to exist?

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

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

Why dont you try to be an entrepreneur ?

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.

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

Product manager?

> 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.

> I do have some shares

Please read the full post before commenting.

Supposedly this equity hardly matters to OP at this point