PayPal

A big name to have on your resume.

Pretty cushy job that actually drug my technical skills down.

Got paid well. Amazing parties.

Fractured technical leadership. Management is a mess.

Massive technical debt and the encumbering weight of a system that has been continually bolted onto with duct tape solutions. The system is almost impossible to actually test and verify.

The vast majority of the technical staff had no idea how the entire system worked. Proprietary SOAP protocol for services. Around 2000 internal services that are almost untraceably dependent on each other and often have duplicated/triplicated functionality.

Little actual will or ability to reign in the system bloat. Basically a lot of senior people had many others running in circles just so they could justify their positions.

At one point we were told that if we weren't making every possible purchase with PayPal, we shouldn't work there. So there was quite a bit of pressure to drink the Kool-Aid.

Internal and incestuous politics with eBay. Very poor onboarding of new acquisitions and newer ideas. From what I could tell, it was mostly a brain drain and then toss mentality for newer, more agile tech and companies.

Rebuild the system from the ground up. Drop the dead weight management and "technical" staff. Best of luck on breaking away from eBay, which was an anchor from what I could tell. Splitting off was a great decision, in my humble opinion.