Any advice for someone getting back in the game after 13yrs at startups?

Congrats on your success as an entrepreneur. 13 years means you did well at it. Speaking from experience, I won't sugar coat it, you're not hireable. 13 years as a startup CTO/CEO says you're not used to having a boss. Corp jobs are all about stfu and doing what you're told. Most hiring managers will pass on you for someone that's spent X years in a corp most similar to theirs.

That said, it's possible. It's usually someone you know really well that trusts you that will get you back in the game. Or companies known to hire founders, rippling comes to mind.

13 years of working for startup companies (10 as CTO and 3 as CEO)

Then

My first thought is to cram leetcode

I think you need to figure out what kind of job you're actually looking for. I'm assuming you mean "something not another startup"; if you're angling for another startup gig I'm not sure why you're concerned.

If you've been a C-level for 13 years, I'm sure not going to be interested in bringing you on as a programmer (unless maybe you have a notable project I'd know about), and probably not as a line manager. It's not just that you should be wildly overqualified, but as cajunboi said, you're not used to having a boss and I'm used to managers who understand what having a boss means. I spend enough time with HR without "my new hire still thinks he's the CEO".

I would de-emphasize the C-level job titles to the extent of changing them to 'Manager' or some such, and if brought up demure with something like "hey, it was a startup...everyone was C-something". Focus on the nuts-and-bolts of doing a job, so to speak. "I managed a team of 15 people and we did X" (citing 'on time' and/or 'under budget' metrics is good here), "I did X things to keep my team happy, productive and had low turnover", "I have a track record of taking a product from inception to X revenue", "I'm a recognized industry expert through my book(s) and participation in X events". Emphasize the team aspect of your accomplishments. Tailor the pitch to the job and don't just spam out generic resumes. And as always, work your network.

FWIW, I came from the startup side too, several times CTO. Now doing my penance in the corp world. :-)

In my experience, it doesn't matter what skills or experience you have in tech, it is only your interviewing skills that count in the getting-a-new-gig game. Start doing interviews anywhere you don't want to work, just for practice, then after your have done 10-20 of those, move on to the places you actually want to work for. YMMV

>My first thought is to cram leetcode for a while but are there any better resources out there? And/or other general advice.

If you're going for staff/principal/senior engineer at Big Tech, this is necessary. (Though I don't think you'll get principal engineer interviews, maybe not even staff unless you have some really notable technical accomplishments other than just being a CTO).

However if you want to work at later stage startups you may not need much practice either.

Finally, you're going for Engineering Manager, I think you shouldn't need to do leetcode. I think most FAANGs etc are going to ask for code reviewing interviews or the like, not have you actually doing algorithmic puzzles.

You do want to practice system design interviews, depending on your skill set, you might be fine and just want to get used to the interviewing process, or you might need to study up quite a bit.

I haven’t had an interview that mattered in 18 years, so I’m not much help there. Once you find something, make sure to take the time to learn about how things work inside the company and what the real issues are before you try to go changing everything. A lot of people show up and start trying to prove their worth through change right out of the gate and make a mess of everything and erode any trust existing employees may have had. Also, expect things will take longer than you’re used to, especially if you’re at a big company. There will be a lot of systems and politics to deal with. This slows everything down and can be frustrating for a lot of people.

My first thought: you should have a good professional network with all that experience. VCs, former colleagues and employees, customers. By the time I had a decade of experience I had a solid network and never had to interview again.

So I would start there. People who know you will see past the titles and want to hire you for what you offer in terms of business value and solving problems. If you’re considering grinding leetcode and doing cold interviews, where is your network?

Then again, I learned after a couple of management roles that I should keep my options open, so I have called myself “programmer analyst” for 20+ years regardless of actual responsibilities.

How about going freelance contracting / consulting? They will probably appreciate your experience as CTO and also your understanding of how to push a product forward.

I've only had side-projects, but one of them was big enough to pay the bills during the best of times. Currently it has hit a speed bump (more visitors, but less orders) so I'm just running it passively on the side, generating a little bit of profit, while I do freelancing.

"My concern is that 13 years of "wearing lots of hats" has not positioned me well for the job market. I know I can be a great principal engineer, manager, or executive but I don't think my interviewing skills (I haven't interviewed for 13+ years) would reflect that."

I assume at those levels your prior achievements are a bigger part. The interview should mostly be about soft skills and "tell me about a time..." rather than code screens. I could be wrong.

See if your investors need and manager types at their portcos. Or see if you can get a junior EM role at big tech.

You don't want to do Leetcode, or apply to any job that requires algo coding challenges (at least for now).

Some good bets for you imho are fractional CTO and director-level jobs at tech companies. For those you want networking and practicing "soft skills" and management interviews.

Curious, why are you trying to get back into corporate/enterprise stuff if you’ve got so much experience with startups? Perhaps consulting might be a good fit?

Use your network. You’ll still need to pass the bar at a FAANG co so start prepping. Probably aim for manager / sr manager type role. Or a director role at a smaller co- best of luck

Why don’t you want another CTO type job?