Pros
Out of all the companies I've worked at, Shyp granted me the most autonomy and greatest professional challenges. The environment is fast-paced and at times crazy: the goal is to disrupt a behemoth of an industry that hasn't seen much innovation in 40+ years. So, if you're looking for somewhere you can slide under the radar, Shyp is not the place for you.
Overall, the workplace is open and, after a few stumbles, has made leaps and bounds of progress on being organizationally transparent. It's a unique startup in that when you speak up about wanting to tackle a challenge, it's almost immediately handed over to you.
Beyond autonomy, the best part of working at Shyp was impact. Even individual contributors were given projects that would have long-lasting impact on the business and its customers.
Cons
The company had a few stumbles from an executive leadership standpoint that it now seems to have recovered from. There was a period where executive leadership asserted strategies on the team that were half-baked, or not relevant because of a bit of an outdated POV (my understanding is that has changed pretty dramatically due to departures, etc.).
Shyp is not a place full of sunshine and rainbows. The work is hard and the challenges are big. Some things work, others don't. This resulted in a period of a rough patch of exploration, where many different things were pursued at once. This is the story of most successful startups, but if it's something that scares you, don't work here.