I took a job as VP of Engineering at a company where this kind of thing was going on.

The guy was on my team. He acted totally inappropriate toward women, made horrible homophobic and lewd comments all the time, insulted the brand and brand creative, intimidated and antagonized others, etc. Toward me he acted officious and friendly, but was not aware that I observed his actual behavior several times from a room adjacent to the open floor plan.

When I talked to the founder/CEO about it I realized she was not willing to discuss any deficiencies in his conduct. I was also at the office late one night and she IM'ed him (seemingly while intoxicated) and flirted with him extensively. I was also pressured by the founder to promote him into some sort of leadership role.

After seeing how he intimidated people (particular junior developers, QA team, etc.) I felt he was not well-suited for a leadership role. He also stirred up trouble and did his best to create a clique and make fun of several people on the team who challenged his technical opinions.

I documented all these concerns with HR and encouraged the harassment victims to make an official complaint about one of the incidents. I explained that it was a tough situation because of the founder's loyalty to him, and that while I was hoping he'd find another job I was sure it would reflect poorly on me if he quit.

The most surprising thing was how his approach (arrogance, hyper-confidence, indignation, loud speaking voice) made nearly all the non-technical people in the organization convinced he was a world class technologist. In reality he had pretty poor technical judgment and many fairly counter-productive prejudices which he was convinced were best-practices. His disdain for QA led to most of the embarrassing bugs the company had suffered, often because of his boorish intimidation of the QA team and disregard for process.

Occasionally he'd show me his code and seem to be seeking approval. He was actually quite insecure and so I tried to give him whatever positive feedback I could. He also claimed to have gotten the past two VPEs fired and threatened to do the same to me.

I realized the situation was bad but figured it wasn't worth playing games to try to "win" when the founder had pretty poor judgment about his conduct and character.

Overall he cost the company millions in lost productivity, and I recently realized he is now the VP of Engineering there. The company has peaked and is now in a mode of loss-mitigation and likely fairly small existence as a going concern that would probably have been better off as a small business and not a VC funded growth machine.

Lessons Learned:

- Decide what is worth fighting for: While being good at politics is a useful skill, is the company worth it? Do you want to win to be part of something you ultimately don't respect?

- Life is too short: If you or others on the team are experiencing stress and burn-out, think of all the other jobs and teams you could be working on that would leave you feeling inspired and productive at the end of the day.

- The founder may not deserve your help: Bad judgement in one area likely indicates bad judgment in a host of areas. This happens to be the one you are most aware of. When a company gets angel funding it gains a salesperson, and so on through each round. So just because this company has capital does not mean it deserves it, only that each salesperson wants to find the next buyer.

- Take what you can: If you do respect some people on the team, get to know them and prepare to bring them wherever you go next. Talent is scarce, and the relationships you make will help you populate your next team with great people.

- Last point: If you work with a founder you can't have a frank conversation with (either because he/she is aloof, busy, or otherwise) consider leaving. Too much is at stake to waste your life working to help build the dream of someone who is so out of touch.