Pros
I'll throw in my two cents that you have very high growth potential in the Pleasanton office, and during my tenure there were many promotions from within, globally. Because Steelwedge isn't really for people who are interested in staying with a company more than a few years, there's a lot of opportunity to step into someone else's shoes after they've gone, and to learn a ton while you're at it.
The best part about Steelwedge is the team, hands down--it's a close knit group with a strong culture and amazing personalities and brilliance. It's still just small enough that everyone knows everyone else. There has recently been a push for better career development strategies, and I think with lots of collaboration between HR and managers this can be done. There are often lateral moves in addition to cross-departmental training, although I believe there could be more of the latter.
The benefits were FANTASTIC, including two health plans under Blue Cross, flex spending plans, two dental plans (Guardian), vision, an open PTO policy (just be prepared for the fact that PTO is based on workload and management approval, so you may need to do some pre-planning to get the time off), gym membership reimbursement, small perks like snacks and drinks in the kitchen, et cetera. When interviewing with Steelwedge, please ask about the benefits.
Cons
There are a few members of the highest management ranks who could stand to learn some management skills and should collaborate more together for a more seamless organization. While it's true that every leader has flaws and things that could be improved, what worried me was management's inability to see and address these issues within themselves. The C-Suite all had great personalities but each lacked at least one fundamental leadership ability, if not many of them.
Work/life balance is tough, but they do allow employees to work from home (which you'll probably do a lot of after putting in your hours at the office). I looked at it as a trade-off for the global experience--giving presentations to India at 10pm or at 7am, or chatting with Japanese employees at tough hours. The UK and Netherlands had a tough time keeping in touch with the US unless they were working well into the evening. Most of the time we could make this work, but expect to work long hours (with a flexible schedule in most cases). The company is small enough that everyone talks to everyone else, so you need to bend a little and be prepared to sometimes talk to people at a more convenient local time for them.
