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.
Like any first employee I've wore multiple hats. From fixing stupid little bugs at midnight to setting up processes for dev, hiring, code reviews, qa etc.
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't want to go through this grind again. And for big companies I don't have the expertise to either pursue an engineering role or managerial role.
Did anyone go through a similar experience? What do you suggest my next steps should be?
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.
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.
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.
You have worn many hats. Therefore in a big organization you have the ability to develop yourself in many directions.
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 should find some (more) recruiters start to knock and that may start to bring you some new opportunities for perspective.
Being your own boss brings a lot of freedom of choice.
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.