Pros
The culture and people here are absolutely amazing and make it a joy to come to work each day. Work/life balance has been great for me and managers are always understanding of personal needs. TaskRabbit is growing very quickly so there is a lot of opportunity to move up if you are coming in at the bottom.
Cons
Where to begin? The app is an absolute mess and is so full of bugs and issues that Taskers are literally losing jobs over it. They can't keep enough engineers around to keep up with the problems so they are caught in a vicious circle at the moment. The organization structure doesn't completely make sense and there is a lot of overlap between certain teams and who should do what isn't always clear. It also makes it hard to get things done because you need half a dozen people's input on any one thing because of all the overlap. Since engineering and the organization are such a mess very few people actually have the tools and solutions they need to do their job effectively. Not to mention support for projects is unevenly distributed so some teams get anything they ask for right away while others languish with broken processes. To compensate for all of these issues management likes to pretend TaskRabbit has a "start-up mentality" which is really just code for the fact that none of them seem to know what they are doing. Then, despite all of this, they are still trying to move other initiatives forward that don't make any sense because the rest of the company is not aligned on being able to deliver.