Pros
The legacy Datto team were not perfect (who is?) but the support, trust and empowerment were great. People would listen to input, and react accordingly. Town Halls were meaningful, and shared meaningful information. Benefits both large and small were valued. If you are ever in the market for some of the best people around, don't think twice - hire anyone from the legacy Datto Supply Chain group - they won't let you down!
Cons
Since Kaseya took over, the experience of working there plummeted. Benefits were removed, often without notice. The culture was worse than something that grows on out-of-date yoghurt. Finance in Miami and in Ireland are an absolute mess, and seem to actively work to stop the company from functioning, and some of their activities are openly illegal. The laughable Town Halls are an hour of Fred the Head ranting and gibbering about how much he loves Microsoft, and how every single quarter is better than the last, but with no facts or figures to back it up. He told us we were getting the Kaseya name over "one of the most iconic stadiums in the world" - turned out it wasn't even the most iconic stadium in Miami! The irony of it only being available because the previous name over the door was for a company that went bust was not lost on us. Datto Europe lost their credit limits with their largest suppliers due to late filing of accounts. Processes that had worked before and supported international tax regimes were changed on a whim, and made ever more complex. Regulatory Compliance requirements were, and still are, being given little attention. In short, Kaseya care only about what happens in Miami, and nothing else. It's a real shame, as Datto was great to work for, and Kaseya really isn't.