Great CEO, great technology and technology leadership. Sales leadership finding its ground.
Pros
Four+ years of my career's best and most satisfying years were spent at OutSystems. FANTASTIC crew, all of them. The engineers in Portugal are some of the smartest I've ever worked with. This company cares/cared about its people. People Ops is TOP NOTCH! I would do it all over again times 10, but... If you are lucky enough to get an offer, take it and don't look back. You will never regret having done so - as long as you don't report through Sales and as long s you don't expect equity - which will remain elusive until the VCs figure out their exit. If you are offered equity, take it. You will be one of the few.
Cons
OutSystems took $55MM from NorthBridge Growth Equity Partners ~1 year ago and the VC is having its influence on decision making and cost restructuring. For better or worse, many quality folks lay (terminated) in the wake of that decision. Northbridge and Paulo will have a great exit. Longtime (lifelong?) OutSystems contributors?... I hope, in the end, you are compensated for your contributions. Most of us will never be.