Ask HN: Selling software to company I work for as an employee

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I've gone through the exact scenarion in your question though, this is roughly the path I took (Estonia & EU, YMMV in other jurisdictions):

- start by going over your contract - is this overall even allowed? Some companies capture all IP you create 24/7, in this case you'll need to get the contract changed or get an exception

- even if your contract allows doing other work (creating separate IP) outside of company time, still ask for written permission from your manager and possibly a skip level or two. I got a written email from my VP of eng and CTO before proceeding.

- you will probably need to _completely_ separate your own work from the company work. This means using your personal laptop, never working on this during work hours, etc. Separating this sometimes can be hard, especially if you get something like a bug report from your employer - you can't work with it until you're off the clock.

- I also completely cut myself off from the purchasing decision - I let them know I was working on a project, gave them a landing page and let the purchasing team do a decision completely on their own

- if you hope to build a business out of this it's best to be upfront about it, e.g. by telling your manager that you might leave to focus on the business full-time if it takes off

All of this assumes you're on good terms with your employer overall.

Better to try develop and somehow leverage it internally or leave and sell it back.

Unless the company bosses are behind this idea you will need to overcome both legal problems and selling problems. For example, instead of buying your product the execs could fire you and hire someone else to do this internally. I see only three ways you might wing it:

1. Talk to your execs (ideally, the CEO) directly and sell this. On failure, be prepared to work on this internally. If so, ask for more money/promotion, which may not work but will not hurt either.

2. Call the other company and offer to improve their product for more money/promotion.

3. Get a techie friend to front for you: he approaches your company, you do the work, he shares the money. That's really grey area (being charitable). My 2c.

If it's something that's specific to your company and there is no market outside it, you have one customer that at the same time has strong leverage over you due to your current employment.

If it's something that could be generally useful, you likely still don't have a market: if your product ever became popular, the big-name company selling the original software could add it as a feature or paid extension and would have a huge marketing advantage over you.

The company you currently work for will likely not be willing to pay much for your work, and might take offense and fire you if you try to negotiate too hard. They could also decide that your new job is writing this thing...

You could try to leverage it for a bonus or promotion or something like that. That's unlikely to capture a significant amount of the value you provide, but so are the other options.

If you think the idea in https://news.ycombinator.com/item?id=44080196 will fly, you could try that. I think it's unlikely to fly but it's the option that likely pays out best if it does fly, and if you approach it carefully ("this is outside the scope of my role and my department, but I could do it in my free time"), you might be able to pull it off with limited risk.

You also need to understand how decision processes work at your company and optimize your proposal for it. If it's more work to get legal to approve the contract with you than to get approval to pay 10x as much to the original vendor to add something half as good as a feature, the vendor gets the job.