Pros
I was an engineer with TaskRabbit for 4 years. The team TaskRabbit (TR) has assembled is one of the kindest & smartest groups of people I've ever worked with. I'm a shy person, but I ended my time there with quite a few friends and close to a big group of people I respect and trust. TaskRabbit is trying a very hard thing. Compared to all the competitors in the space, they treated the Taskers (workers/contractors) with the most respect & support of any company the sector. The Product is centered around the notion of giving them a choice (when to work / where to work / how much to charge, etc), rather than shoe-horning them into negative relationship **cough** Uber **cough**. There are legal limits to what TaskRabbit can to do support the Taskers, but they’ve always tried to raise the bar. TaskRabbit has even started trying to work with government to change the laws to enable them to offer Tasker things like health care, etc. For a startup, the benefits are on-point (salary, health care, 401-k (no match), etc). You get a trendy SOMA office, new computers to use, free lunch, etc. If you care about diversity, and you should, TR is a great place to work. They’s got one of the better ratios in San Francisco (gender, race, age, etc). TR walks the line of having a good work-life balance with a passion for the product. Folks rarely work on nights/weekend, but if there’s a project deadline looming, folks will happily chip in. As an engineer, I think our ~15 person product team was managed well, and we all had input into the direction of what we were building. We got to influence the product roadmap, have hack-days which really did birth new products/partnerships, etc. We had a fair balance of time to work on ‘tech debt’ with new features. We had the ability to upgrade our tools, and ensure that we used the “best tool available”, within reason. We always used new versions of Rails, were one of the first react-native apps, etc. Heck, we even won an Apple design award for our iOS app.
Cons
TaskRabbit a startup, and startups are hard. By definition, startups are risky endeavors doing an uncertain thing... with the possibility of big rewards down the road. Many of the other reviews on this site seem to forget this. Obviously, TR won't pay as much as Google or Apple will, and yes TaskRabbit had some road-bumps along the way (I was there for the "marketplace pivot" and a round of layoffs), but that is how experimenting works! This adventure is why you join a startup trying to do something hard. And yes, changing America’s relationship to domestic labor and creating equitable jobs for a lower-skilled temporary workforce is *hard*. I've worked for quite a few startups, and TaskRabbit handles the above with a clarity and openness that’s rare in Silicon Valley. That said… don’t expect smooth sailing at any startup, and that includes TaskRabbit. As far as the Engineering/Product team is concerned, it is a small group with big dreams. There will *always* be ideas that won’t make the cut, and won’t be worked on. Most of the time TR made the right choice on what to prioritize, but sometimes they didn’t. TaskRabbit is a small company with only ~50 full-time employees. With that in mind, career advancement can be difficult. If you want to end up as a Director/Manager, and there’s no one to manage… you might be out of luck.