Pros
One thing DigitalOcean has is really good perks - you can work remote pretty much whenever, fully pay for MTA card, lunch everyday, team outings, gym reimbursement, good insurance, etc. But perks aren't everything - they can't create a culture (with terrible leadership) and it's really easy to tell when the business isn't doing so well when they start cutting back. Honestly, the "working" employees are the best thing about the business.
Cons
The CEO of the company is not a leader, is unapproachable and is slowly driving the company into the ground. He is disrespectful to almost everyone and his ideas are always correct. They are pushing for diversity, but it doesn't seem like any female leaders are liked. I would be surprised if the board didn't push him out by the end of the year. On top of it, another member of the exec team is a brother (who left and came back - never a good sign) and several Directors/Managers throughout the organization are related to one another - conflict of interest? Turnover has been terrible - reading in a newsletter that 2-3 people left every few weeks is absolutely insane. They preach an amazing growth opportunity, but continue to hire outside of the organization because they have no career paths laid out or development plans in place. They ARE well funded, but don't mistake this for having great leaders. The company has been slow to adapt to the enterprise sales trend of technology companies for revenue growth and is now scrambling to fix it since they aren't hitting projected revenue. They have relied on word of mouth and their "community" for business and are just now realizing they need a sales team...5 years after inception. They underpay a lot of teams outside of engineering (they are the most important) and then do "off cycle comp reviews" just to say they are "working to fix" pay inequities. A lot of managers are inexperienced, which isn't the bad part - but it's that they don't have the leadership (or qualified leadership) to train these young professionals to succeed. They have a ton of values, but in reality, it seems like the executive team is exempt from all of them. I won't continue to ramble on, but you get the idea. It appears great on the outside, but inside it's is a mess, their growth is slowing, and you need to be prepared to be frustrated and stressed everyday with no explanation and a "this is the way I want it" attitude from the top.