|I realize that everyone makes their own decisions and it's difficult to compare, without knowing details, but I can't think of a better place to ask for advice.|
I am 35 and have been doing IT/Ops(devops)/Security for close to 20 years. I've done management (small teams), but I am much better (and comfortable) with hands on and dealing directly with technology/design. I now have a choice of two companies:
A - a larger company, ~1000 people. Grew rapidly over the last year(maybe too much), since they got bought out. The culture is very much "startup-like". Biggest in their market with 10s of millions of users. Relatively well known, even to someone who is not using their product and googling will quickly let people find out. Offering the most money and want me in a technical/strategic role (non-manager, at least at first). There are some very interesting problems to solve (scale & complexity) and they have a lot of brilliant people, which is a huge attraction. The downside is really being a medium fish in a big pond and the impact that I'll be able to make there is probably more limited.
B - is a small (profitable) startup, probably <50 people. They are growing, but at best they are 3-4th in the market, behind a few 800lb gorillas. The role is still very much hands-on technical, but leading a team in addition to that. I can write in whatever fancy title I want. The problems they want to solve are interesting, but much more narrow in scope. The compensation model is heavy on bonuses/incentives/revenue goals and upside is potentially higher. Name recognition isn't quite as high, though people do know them.
So, it's a two-part question:
1. Career-wise, is it better to be in a smaller company with a big title or a larger company with a less impressive one?
2. Most of my time has been spent in smaller shops, where I am usually the most experienced/expert guy. How is it working for a large company with a lot of talented people?