Pros
CarGurus is a fun, creative and relaxed atmosphere. You'll work with people from all backgrounds. You'll get catered lunch every day, a gym membership, gorgeous views, free snacks, coffee/cold brew. You'll be free to plan your day as you see fit, as long as you hit your metrics. Everybody is kind and welcoming, and you'll feel like you belong. It's low stress. The products are great, and they help a lot of people. It is a wonderful place to work.
Cons
Once the honeymoon is over, the job gets mind numbingly monotonous and simply doesn't change. You'll have to hop on long calls with angry car dealers and be ill equipped to deal with their objections. You'll have piles and piles of charts, graphs, pie charts to resell value, but 9 times out of 10 the clients know that the company lets them cancel and then come back, rinse and repeat. They have way too many managers who simply do not provide a lot of value to their direct reports other than telling them to do more. They've outsourced a lot of complex work to overseas call centers. This will lead to issues down the road.