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I'm the technical co-founder of a small software business (two people). We built some very niche enterprise SaaS software and have a few big clients who pay us every year. The software is now so stable, and the niche so saturated, that my work obligations can be met by sending a few emails and putting in a few evenings and weekends every year. As a result, I would like to get a job somewhere – not for the money, but because I genuinely want to join other smart people to work on challenging problems. In other words, I consider myself very fortunate but I'm bored.

I started this business right out of college, and have spent five years on it. That makes it the main item on my resume, so I have to make it look like a big deal – mission-critical software for big, well-known clients, thousands of users, complex full-stack architecture developed entirely by myself, etc. – all of which are true.

Now if I were a hiring manager, I would (perhaps) be impressed but also very worried: if this guy maintains such big and important software, how is he going to have the time to come work here?

Indeed, I have now applied to a few jobs that, at least on paper, I am more than qualified for. I tried to explain the situation in my cover letter and have either received rejections outright or simply never heard back, but never got an interview. (Yes I know, this could have other reasons.)

I can't sell the company even if I wanted to; there is nobody to sell to in this space, and our support contracts still have a few years to go. Realistically, my partner can still do most of the client-facing work, and she would be happy to.

How do I credibly convey that I:

  1. Am sufficiently accomplished?
  2. Actually available for full-time work?
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    If you're bored, and want to work on "challenging problems" but don't need to work for the money - why not do that from within your current organization, find another problem to solve, hire some smart people, and get cracking. Let the existing product bankroll this next one. Separately, there is always someone to see a profitable business to. Find a larger vendor of enterprise software and show them the profit statements. Maybe they'll take you with them, and you can solve both problems at once. – dan.m was user2321368 Sep 25 at 16:47
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    Just to continue - your ability to work on interesting project and with smart people is going to be much higher when you're at the top, then if you're at the bottom some place else. So figure out how to either do it from within your existing organization, or figure out how to merge your organization into another one. A big difference joining as a "partner" than as a bottom level developer. – dan.m was user2321368 Sep 25 at 16:51
  • Thanks @dan.mwasuser2321368 – I'm primarily looking at corporate research labs. Hard to do that kind of work on my own – sk29910 Sep 25 at 18:09
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    Start a family and focus on that, work should be a means to an end – Kilisi Sep 26 at 1:46
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    @sk29910 Contrary what others posters say I think you have all assets to be a good candidate: experience, out-of-the-line thinking, knowledge, spirit and so on. Perhaps these are not the things that would be valued by big corps but by smaller companies definitely. Ever thought about joining a startup? or an overseas company expanding to US? why shan't we get in touch directly? – Pawel Debski Sep 26 at 22:20
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You can't.

You didn't quite phrase the manager's fear right:

Now if I were a hiring manager, I would (perhaps) be impressed but also very worried: if this guy maintains such big and important software, how is he going to have the time to come work here?

That's not the fear. Let me alter it a bit for you:

Now, if I were a hiring manager, I would be impressed but also very worried: if this guy maintains such big and important software, what happens when both projects demand his attention?

Sure, right now you might be available for a 40 hr/week job. What happens when a new OS patch comes out and destroys some element needed for your service? What happens when a new SSL bug comes out and requires an emergency security patch put into your code? What happens when a client gives an urgent call saying, "We think the service causes a networking flood! Every time we call your service, we get back a flood of traffic that's causing us severe network slowdowns!"

That's what the manager is worried about. You'll be working on getting the new Floobar system up and running for them... except you'll suddenly have to take a few weeks of absence because something's gone wrong with the other project. They're worried that this new job won't be the higher of the two priorities (quite rightly, since there would be a lot more money on the line with the former job), and think to themselves: wouldn't it be less risky to hire someone that doesn't have this potential problem?

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    You've put it much better than I did. Thank you. That's not the answer I was hoping for, but clearly my concern is justified. I'll have to rethink my strategy. – sk29910 Sep 26 at 2:35
  • But to be fair, any other important hobby or life event (e.g. children) can make you less available for a job. – Michael Sep 26 at 19:31
  • @Michael The difference would be that this candidate would have all the same potential for an absence for "life" reasons as any other candidate + absences for an important business venture. – jmathew Sep 26 at 21:32
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This is a good example of the "exactly" argument. It can be found in any book on closing sales under "overcoming objections". You turn the objection into the reason why your argument is correct.

"Your product is more expensive"

"That's exactly why you should buy it, we are higher quality, and thus more expensive, but a far better VALUE"

Or, in your case.

HM: I'm somewhat concerned that you own your own business.

YOU: That's EXACTLY why you should hire me.

Then use the very words you used above

The software is now so stable, and the niche so saturated, that my work obligations can be met by sending a few emails and putting in a few evenings and weekends every year. As a result, I would like to work for your company because I genuinely want to join other smart people to work on challenging problems.

There are many successful people like you who have done the exact same thing. Use that as an asset.

Then, you can field all those nasty interview questions with the same justification.

HM: Why should we hire you? You: I'm already a successful developer that made huge profits for his own company, I could do the same for you, et cet.

How do I credibly convey that I a) am sufficiently accomplished and b) actually available for full-time work?

The fact that you've set your business up to essentially run on auto-pilot screams both A and B of your question

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  • Do you have a reference for the “exactly” argument? I’d love to see how this generalizes to other situations. – Dan Romik Sep 27 at 5:43
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    I'm in a similar situation to the OP, and went about getting hired at my current company in this way. The main impact was that I had a few conflict-of-interest calls with legal after I was hired, to codify that I continued to own my own business, and that the two didn't compete. – Itinerati Sep 28 at 19:14
  • @DanRomik It can be found in any book on closing sales under "overcoming objections". You turn the objection into the reason why your argument is correct. "Your product is more expensive"------"That's exactly why you should buy it, we are higher quality, and thus more expensive, but a far better VALUE" – Old_Lamplighter Sep 28 at 19:51
  • Interesting, thanks. For those of us who aren’t familiar with sales techniques, it would be helpful if you edited that into the answer and makes your suggestion more compelling. – Dan Romik Sep 28 at 19:54
  • @DanRomik Done, thank you for the suggestion. – Old_Lamplighter Sep 28 at 19:57
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Try job fairs.

The first rule of getting a job is to tell a story, and you have a great story to tell, but no one is hearing it because they never get past your resume. So go to the places where you can lead with the story. Find the job fairs in your area that are looking for people like you, go to them, and hit up the small companies. That will let you start with your spiel of who you are and why you want a job and why you're worth employing, rather than have their first impression be one of confusion and insecurity.

Better still, the smaller the company is, the closer the people at the job fair are going to be to the people who make the hiring decision... which makes it a lot easier to work through any uncertainties while your'e there. It also allows for more flexibility in a lot of ways. You're someone who would be very useful to a bunch of these places, but you're unlikely to be exactly what they're looking for, so flexibility is good.

Finally, be aware of what you are, but also be aware of what you are not. Post-college, you've only ever collaborated with one other person, on one codebase, that the two of you built from scratch. It is highly likely that you have some really bad coding habits that you've internalized and are going to need to purge, and given the success you've had, you may well be resistant to learning such things. Everyone with any experience who looks at your resume is going to know it. I'd suggest that if you want to get a job, you accept this, internalize it, and be willing to acknowledge it in your interviews. Indeed, if you think of this (and sell it) as you trying to get a better understanding of correct coding behaviors, that will probably serve you well, both for yourself and for convincing people to hire you.

Try open-source.

If it's literally not about the money, and you just want to work on interesting problems with smart people... then try doing just that. Open Source communities are a lot more flexible about who they'll take, and you can find a problem that seems interesting to you. It won't put any money in your account, but you don't seem to need that. It will give you contacts, though, and it will absolutely give you things you can put on your resume, both of which will help in getting a job if you ever do again need money.

As a side comment, with that plan I'd also suggest that you try to put about 6 months of expenses away in an emergency fund, just in case, but that's good policy in general.

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  • Job fairs are a great idea! And re: coding habits, that's a very valid point. I've definitely become very tolerant to technical debt, to put it charitably, and I notice it every time I work with others :) – sk29910 Sep 26 at 2:32
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How do I credibly convey that I a) am sufficiently accomplished and

Some client testimonials? List a few projects you've done (even if it's only features in your SaaS) that demonstrate your capabilities. Some would tell you to show code but I've never had to do that to get a job (except when I first started in the industry).

b) actually available for full-time work?

Don't overthink it. I also have my own SaaS business. Good employers aren't surprised if an engineer has his/her own business. They know you want to get paid and that you're willing to work for pay.

They will assume you're available for full time work simply because you're applying for that. Or they will outright ask you if you're available. Instead of saying, "maybe", you say "yes". Of course you're better off going for jobs where there are no micromanagers and schedules are flexible. The kind of job that expects workers to punch a time clock and account for every second of the standard business day is probably not a good fit.

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I encourage you to look for openings at small businesses. In a large organization, most employees are disconnected from understanding "where the money comes from." In a small organization, having employees that an understanding can be a very valuable asset for a small business.

About 12 years ago, I applied for a position at a 20-person company. Prior to that, I had been running my own business for about 15 years. I got the job at the 20-person company and ended up working there for about 8 years. After the interview, the owner of the company told me that one of the reasons that they had chosen to interview me was because I had been working for myself. The company owner said that it had been his experience that people who run their own business have an understanding about where the money comes from and where it goes in a business. I agree, and I think that is something valuable that you can offer to the right small business. That would not mean much in a larger business. Even if you want to eventually work for a larger business, working for a small company for a few years would be a good way to transition to that goal.

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