Pros
I've worked at Tailwind for quite a while now, and it's been a fantastic place to learn and grow professionally. The team moves fast and there are always a ton of interesting problems to solve, and team members are always given a large amount of latitude to solve them. You're never stepping on people's toes. In general, the more you value independence and creativity at work, the more you'll value working at Tailwind. There's definitely less structure as a result, but again, I find that kind of environment really rewarding and fun to work in. The people here are all incredibly sharp, and you'll learn a ton trying to solve whatever your problem your team is tackling. And even though it can be fast paced and challenging, the company culture does promote a healthy work life balance. Benefits are fantastic, as are salaries (we've moved to a geo-agnostic salary model, and salaries are all pegged to NYC rates regardless of the employee's location). Tailwind is also fully remote, but does have an OKC office for those in the area who want to use the space. The leadership team is great, and works to maintain transparency, solicit employee input, and is generally responsive to issues surface by employees. One valid complaint called out in every negative review is one of our co-founders, who was also the head product. He had a toxic management style, which is why reviews here are polarized -- satisfaction at the company was highly correlated with whether or not you had to work with or adjacent to him. (Spoiler: I never did). He's no longer at the company, and the current VP of Product has been an absolute joy for folks in the company to collaborate with. I wish it hadn't taken so long to permanently address the issue with this co-founder, but I understand why it was tough given his position in the company. The CEO has always been the polar opposite of his partner in these respects.
Cons
The typical things that come with startup life -- it's fast paced, but a lot of fun. It's a challenging environment, but for people who like that kind of innovative, collaborative, startup environment, Tailwind's a great place to be. Right now, the leadership team is lacking in diversity, which is unfortunate. I hope that's something they focus on addressing in the future.