Pros
Streak is a small, nimble company that puts product development and the wellbeing of its contributors front and center. I could not recommend working there more, especially if you are early in your career. It will help you set a firm benchmark for the type of quality you should expect from future roles. They have the stability of a larger company, but their size allows you to wear multiple hats and to learn a lot.
Cons
The size of the company makes career mapping somewhat difficult, particularly in the customer facing roles. A lot of stellar Customer Success people do wonderfully and then outgrow their roles and move on to other companies (not a terrible thing, but worth noting). The sales team is somewhat similar, leads are completely inbound and product qualified. This makes selling somewhat easier, but limits the growth potential of the team/company. The pool of leads is naturally limited and so the growth of the sales team is as well. They've discussed putting more into marketing efforts, but to my knowledge this has not had tremendous success as of yet.