Pros
The mission of the company is really interesting. Facilitating a global workforce really helps pair entrepreneurs with resources that would be hard to find otherwise. They enable a lot of innovation. The product in really impactful b/c it is the livelihood for many freelancers and is a crucial tool for business owners. Also, every Wednesday employees get to work from home which helps the practice of collaborating online. It's an important skill b/c UpWork uses it's own platform to source talent. My entire development team was remote in the Ukraine, Russia, and Moldova. They need to target the enterprise more b/c that is where the revenue opportunity lies.
Kontras
For a long time UpWork didn't know what it wanted to be when it grows up. There was not a good strategy for growth to the point it was almost irresponsible to investors. The code is very fragmented and there is a lot of code debt. Getting features launched takes a ton of effort. They were neglecting the enterprise, but now they have changed course and hired a lot of sales people. But before their features were designed for people with 5-10 contractors. They need to think bigger.