Pros
Overall, Roadtrip is a super fun and relaxed environment to work in. People are great there and make the company worth staying at. For the industry, the pay and benefits are decent. Relatively low-pressure work expectations. There is a solid "get s**t done" value here which often translates to rushed or not thoroughly thought-through work, but as long as it meets the deadline and looks presentable that seems to be fine for execs.
Cons
Upper management and execs are completely rudderless. There have been attempts at creating strategic "vision" and goals, but they often get arbitrarily changed when a new exciting opportunity pops up with a large paycheck attached to it. This then completely side tracks teams to execute on it and derails most planned work leaving much to be desired in terms of long-term stability. If you need a more structured work environment with measurable outcomes, then this isn't the place for you. You need to be ok getting constantly distracted and working on projects that don't often amount to much. Pay is decent but not very competitive when compared to the market. There's also a lot of favoritism and "legacy" employees here which causes some internal friction when trying to navigate hierarchies, pay equity, etc.