Pros
A lot of places say they have collaborative teams, but CarGurus is hands down the best example of that I've ever seen. Helpful, sharing, and open to new ideas: it is all baked into the culture. Even non-work things, like the company's charitable giving, is run with the same values. The technology challenges are many, and very interesting, as the business continues to grow and evolve. The level of trust in sharing longer range plans is impressive, and definitely helps align our technology with those goals in practical ways. The work/life balance is very good. Everyone is very focussed when at work, but can relax and recharge when at not. The hybrid work scheme in the Cambridge offices works well, although I do wish more people showed up more than the minimum two days a week -- meeting in person is so much more productive than by Zoom. I would have thought the allure of nice (free) lunches would be stronger :-).
Cons
Some of the technologies in use are rather old, which can be annoying. For example, Java 8 is still widely used, with a smattering of 11, and Go is similarly stuck in the past, at 1.17. For those of us used to the newer features of those languages this can be a drag. The office at 2CP is noisy, especially with the construction going on on the floor above. It also seems like the air handling system is being run at max, which creates considerable background noise (I'm guessing that's due to Covid mitigation.)