Ask HN: 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.

> Speaking from experience, I won't sugar coat it, you're not hire-able.

No sugar coating needed. That's why I'm asking this here, because I already had a hunch that was the case and figured if any group of people could have some experience with this situation it is the HN crowd.

I’d agree with the parent that your biggest challenge is going to be able to deal with a boss.

If you can get through that and make it clear in the process you should be more than fine.

If getting interviews is hard having a title of CTO or founder on your resume you change it to Director or Staff just to get into the process and explain it on the interview.

Make it clear in the interview you are ready to be a good office drone. Say you "respect the chain of command". Managers love that.

Make it clear you are not a primadona.

You are hire-able. Just wipe away any preconceived judgements.

Can confirm, recently had trouble going back to corporate after working as CTO of VC backed startup. Hiring managers, despite my very good resume, judged me very hard and were nervous about having me on the team.

How'd you end up pulling through it?

I'm going back to my previous employer, where they have a written track record of what I did at the company. But even then, many teams at the company do not want me, and feel like I am both overqualified for the technical roles, but also underqualified/a bad cultural fit to lead a big engineering team

Sorry to hear that. Sounds like you and I are kind of in the same boat.

Unfortunately my previous employer that wasn't a startup no longer exists (it was 14 years ago after all, they got crushed by the 1..2 punch of the dot com crash and the 2008 recession).

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. :-)

> I think you need to figure out what kind of job you're actually looking for.

I don't want to be an individual contributor but my issues are two fold:

1. I found most management jobs want me to have managed more than 15 people and a low seven-figures budget and 15 is a non-starter.

2. I've been told (on HN, actually) a lot of companies these days ask coding questions even for management roles.

I could be wrong on one or both or those things but they are my working assumptions (the first one being based on job listings).

So I've kind of resigned myself to the idea that the only senior management or executive job at an established company.

> If you're angling for another startup gig I'm not sure why you're concerned.

I'm pretty sure (ok... 100%) I could get a leadership role at an early stage startup but the reason I'm looking is because I need a stable paycheck and benefits (for various life reasons) and most of the early stage startups I see are only paying equity with a token salary for leadership roles. If startups could pay well I'd be continuing to work on my current startup.

What kind of cash comp are you looking for? I assume $100-200k leadership roles at early startups should be pretty trivial for you to land with your experience, but maybe that's a token salary to you?

I need to make $150k minimum to support my expenses (mortgage + 2 kids). My previous startup I was making $175k but my current one I am trying to raise money on (and haven't been able to yet) and the potential investors are opening saying they won't want the founders to be making more than $100k. Which is kind of why I'm looking, even if I get a seed round I won't be able to pay myself enough to cover expenses.

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

It's important to practice story telling in an interview. And the best way to practice is to do actual interviews at place you don't want to work. It also boosts moral to get offers from these places knowing you have a backup plan.

Ironic to give this advice with so many people on HN and elsewhere bitter about companies ghosting them after interviews. I wonder how employers might adapt their recruitment processes if practice interviews become a thing.

Not saying it’s a bad idea but it does seem a little bad faith.

This is kind of why I haven't replied directly to this one yet. I don't know how I feel, ethically, about wasting interviewers time. I've been on the hiring side of the table a ton in the last 13 years (just not on the other side of the table) and I'm not sureI'd be trilled if I found out candidates were doing this to me.

With that said, ethics aside, it does seem like a solid way to get practice.

I suppose you've fundraised at some point in the past 13 years. If you have, the advice you probably received was to start with the tier 3 VCs, hone your pitch, and move on to the VCs you really wanted to work with once you had your pitch nailed.

The same principle applies here. The more interviews you do, the more comfortable you'll get, the better it'll go. And who knows, it might work out with one of the first companies you interview at!

That sounds like a good idea but oddly enough the first startup (the one I was at 10 years) only raised a friend and family and we were able to land customers and bootstrap from that and the second one I bootstrapped out of a little cash I got from the first one so no investors to go to per say.

Thanks for the advice, though!

> if practice interviews become a thing

They've always been a thing; at least in SV.

No, not always. I have worked in the software business too long to buy the “always” line. Even if true that doesn’t make it OK to waste the time of multiple people who go through an interview in good faith.

People who need to practice tech interviews, while probably optimizing for the wrong thing, have plenty of resources available to do that.

"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."

This has been the opposite of my experience.

I tend to interview very well... at least in the past. My confidence is shit now. I had mediocre skills then (deteriorated now). But I had a wealth of situations to pull from when they wanted me to tell them about certain times in my career. The code screens always killed me because I bounced between tech and teams too much to become a true expert. Now, this was at midlevel positions, not the higher level stuff the OP is looking at. I would hope the code screens are less of an issue for them. I'm fucked though.

yeah, the thing is tech interviewing skill don't compound or accumulate. you can get a job today, work for a year or two. it doesn't mean you've become good at interviewing. you will just be back where you started.

yeah, it sucks OP couldn't make his startups work. but if there's anything with a negative ROI in terms of learning it's interviews. you can do leetcode / behavioural etc, after 2/3 years it doesn't mean you're now a pro - if you stopped doing it

find places that appreciate builders OP. and that have less than 3 interview rounds.

Practice interviews only makes you skilled at interviewing for places that you don't want to work.

>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.

> 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

You may be right.

The companies I was CXO of created some pretty impressive intellectual property (deep tech; which I coded the v1.0+ for personally) and two books (major tech publisher not self-published). You're probably running code I wrote on your machine if you are on a Mac or Linux. Can't say much more without doxing my throw away account.

But I'm not sure any of those things would come across well on a resume, unfortunately.

> 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.

Interesting, I've heard that opposite. Good feedback.

> You do want to practice system design interviews.

Good idea. What do you think the best way to go about that is?

>The companies I was CXO of created some pretty impressive intellectual property (deep tech; which I coded the v1.0+ for personally) and two books (major tech publisher not self-published).

Ah. My mistake, I'd guess that is likely to get staff+ level interviews at Big Tech.

>Interesting, I've heard that opposite. Good feedback.

That managers have to do DS&A coding rounds at FAANG+? Maybe some, I don't think the bar will be near as high as the IC route.

>Good idea. What do you think the best way to go about that is?

Well, I don't think this is something you can fake, but if you've been working on deep tech, you don't have to fake it.

I'd go against the grain of reading 'system design books' and say instead read (some of) the actual code and design docs for large popular web scale open source projects (stuff like K8s, PostgreSQL, Cassandra, memcache, Spark etc).

That should be enough to get a deeper understanding of how to design large scale systems.

Then do a few practice interviews at some place like pramp.com or interviewing.io, just to get used to talking about it with someone.

> That should be enough to get a deeper understanding of how to design large scale systems.

Both my startups actually hit scale so I already know system design pretty well. I was actually an early adopter for K8s and we were using Docker before it was even GA. What I don't know is how to interview for it, since a down side of working at a startup is you have very few sounding boards to catch up with terms of art. The priority is on shipping. I'll check out those sites you mentioned. Thanks!

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.

> considering grinding leetcode

Even with a strong referral a lot of places won't let you skip 100% of the coding interviews. It might just fast track you past the technical phone screen.

A referral is one thing. I mean knowing the hiring manager, or an executive, or someone who has direct contact with them.

Only a small fraction of companies, mostly in SV, do coding interviews at all.

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?

Being a startup CTO doesn't necessarily translate well to CTO (or even VP of Engineering) at more established companies. They are different skill sets. I can probably get a startup CTO / technical cofounder role at a pre-seed or maybe even seed company but at that stage the pay for execs is usually mostly equity and I need a salary to be able to support my family (that's why I'm looking vs continuing with my current startup).

Not sure what it’s like where you are based.

Might be worth looking at companies with a similar sized dev team that are growing and need someone to run the tech team.

So skip the startup/tech cofounder and find the ones where the initial stage is done and either the existing person wants to step away or is no longer “the right person” for the current role.

These roles are often less equity and more salary.