Pros
I think Cloudability is a great place to work. You'll be afforded the opportunity to become a domain expert in all things cloud, which will only increase in value as time goes on. The engineering team is top notch, and working with the principal engineers on the team is a great way to sharpen your tools and get even better at your craft. You'll be challenged here, you'll have to stretch and get a bit outside your comfort zone, mainly because there is a very dense technical domain that the product functions in, so you'll spend a lot of your initial time getting familiar with the intricacies of public cloud services and how they relate to the product. I enjoyed the culture at Cloudability. The Boulder team I worked with is a very close, tight knit group. We always strive to include people and insure that they feel comfortable and are given a lot of opportunities to contribute and grow. Our team always made it a point to hang out and spend quality time together, which to me is the sign of a team that is high functioning, high trust, and high accountability. All things I crave in a work environment. I believe strongly that the management wants the best for employees. I felt that management was approachable, and I think all of the C-levels in the company genuinely care about their employees. I've had a few personal interactions with the CEO, and I felt that he was authentic and available.
Cons
I think Cloudability is still, in many ways, an early stage start up, despite its size. This can be a pro or a con, depending on what you're looking for. I think the team and company will continue to mature and grow as time goes on, but the immediate feel of the experience will be like an early stage start up, so make certain that you're prepared for that.