Pros
Cask is a flat organization, with a heavy focus on Engineering. I would guess that 75% of the company are engineers. All Engineers report to the VP of Engineering, directly. Engineers are assigned into teams, focused on a single project or major features, and self-organize. Direction and goals are given, but technical details are left up to the teams to decide. The management style is particularly hands-off, allowing engineers to work without impedance. Compensation is comparable with other startups looking for top talent. The company has an "unlimited vacation" policy and allows for work from home, as needed. Catered lunches are provided, free of charge. Snacks and drinks are stocked in the office at all times. The office is just around the corner from the California Avenue Caltrain station, so public transportation is readily available. The office itself is open, with no cubicles or offices. The CEO sits amongst the rest of the employees and several conference rooms are available for private conversations. The company's products are open source and involvement in the open source community is vital to an employee's success.
Cons
Cask moves very quickly. This can lead to some pressures both in the office and at home as deadlines approach. There is a tendency to work on new features and code until very near the release, which increases pressure at release times. The flat organization can sometimes lead to small "silos" and cross-team communication must be initiated by the teams, themselves. Sometimes features and direction are changed based on customer feedback or requests without being properly vetted before becoming requirements. This leads to long discovery times, which can interrupt the forward momentum of a team.