Pros
Simple, in retrospect, was one of the best places I've worked (until it wasn't). The mission of the company truly is great, and I still believe they're shaking up the broken banking industry. The product is beautiful and intuitive and I was proud to be a part of their history. Their pay and compensation are good, with the usual tech company perks (nap room, beer on tap, great healthcare, ample time off, etc.).
Cons
As Simple grew, various part of the company felt very disconnected. Products were released and major decisions made which had a negative ripple effect throughout the company. This is partly because Simple's culture applauds taking risks (and they did often pay off). In the early days of the company, all employees concerns seemed to be heard. As time went on, the consequences of major decisions had the most profound effects on employees whose voices weren't heard. Workloads became unmanageable and burnout was palpable. Simple never seemed to get their internal structure right. Possibly to save money, I'm aware of several instances of managers absorbing additional teammates when they had no interest in doing so, which left many employees without proper leadership. In other instances, employees who left did not have their positions backfilled, amplifying the workload on their team. Ultimately, there were two rounds of layoffs (public knowledge) that felt very poorly handled and left the company morale low, and it doesn't seem to have recovered.