Pros
The life insurance industry has sort of an unseemly reputation but the founders do an excellent job of showing that an insurance company can align itself with the interests of its customers. As an engineer, the product and design folks I interacted with were top notch and we had a good working relationship.
Cons
When things went badly they went very badly very quickly. It seemed like we went from record growth to huge layoffs overnight. Even though Ladder is a still a startup they've reached the point where they need to adopt aspects of a more established company. My manager was new to managing and while he was great technically he struggled with the communications aspect of being a manager. A more mature company would have had policies and procedures that could have helped him out. Instead this resulted in things going unaddressed until they became serious issues.