An open letter to Kaseya: How to keep a Datto customer

I am not a fan of Kaseya. When I heard the news about the acquisition I had given Datto notice not to renew my RMM contract within 10 minutes. We still have a little over 2 years left on the contract so plenty of time for us to have a smooth migration to another tool. Since then I have been thinking a lot about what it is I love about Datto and what it is I dislike about Kaseya and more importantly what Kaseya would have to do to get me to change my mind and revoke my cancellation notice. I think 2 years is the perfect amount of time to be able to make the decision as it is enough time for Kaseya to have ruined Datto or for Kaseya to have made positive change. Here is what Kaseya would need to do to make me happy to use them as a partner:


I would not be able to sleep at night if I had VSA installed on my customer endpoints. I have 0 respect for Kaseya from a security point of view. Whether it’s the VSA breach, where if anyone had done a security audit of the VSA code, the massive red flags would have been highlighted. Or the IT Glue issues where AWS end of life notices were ignored for 6 months and Kaseya failed to upgrade insecure databases before it then caused major issues.

To fix this, put Ryan Weeks in charge of company wide security. Listen to the sweeping changes he will want to make to Kaseya’s security culture and implement them. Security should be Kaseya’s number 1 issue, it is going to be a painful process to get where Kaseya needs to be but will be worth it in the long run.


Invest in development teams and products. One of the things that got me to move to Datto RMM is I was told they want to be the leading RMM on the market and then they had the release notes to back it up. Look at the previous versions here to see what I am talking about The release notes for a single month of Datto RMM are more than what IT Glue or other Kaseya products deliver in a year.

Fix your contract T&Cs

There are currently two MSP vendors who have snuck terms in their contracts that mean I will never do business with them, while these terms exist. The first is Kaseya with the 3 year autorenewal minimum on any original term contract. The other one is Connectwise. I recently found out they have added a wonderful clause to their API agreement saying that you cannot use the API to migrate your data away from any Connectwise product.

The clauses are both tacit admissions that the companies doing them know they have a weak software offering and they main strategy to retain customers by not allowing them to leave. Make good products people want to use and I will be the first to write a migration script to get people there. Who knows if Kaseya can improve enough I might be writing a Hudu -> IT Glue script one day!

Stop being the place where good software goes to die

The main reason people are upset with the purchase is we have seen what Kaseya has done in the past with every other purchase. Look at IT Glue. It was the market leader. It did things no one else was doing for MSPs and was lightyears ahead of any competition. One day development came to a screeching halt. New features started being half baked and charged as addons. The ideas forum became a graveyard of people begging for basic features and them being ignored. Then about a year later we found out Kaseya had purchased them in secret a year before. Thankfully due to the aforementioned Datto RMM release notes it will be incredibly easy to see when Kaseya start to do this to Datto RMM. We work in technology, companies charge us a monthly fee for using software. This means you have to constantly fund and develop the software or competitors come along and make the incumbents look like idiots. Case and point Hudu. There is no reason anyone who hasn’t been tricked into a 3 year contract should be staying on IT Glue. Hudu has now overtaken it as the best product around.

Fix your Culture 🙁

The recent incident involving Huntress shows Kaseya has a huge problem with their internal culture. The fact that anyone thought it was ok to bully anyone like Kaseya tried to with Huntress shows there are huge issues internally. Datto while not perfect would never sink to that level. This needs to be addressed top down during the merger to make sure Datto’s culture rubs off on Kaseya and not the other way round.

Be part of the MSP Community

We know Kaseya are reading /r/msp thanks to the above Huntress incident. Start to engage with us. Have representatives across the Kaseya products on /r/msp and places like MSPs R Us and MSP Geek. It is going to suck to start with, Kaseya has a well earned awful reputation, but actually interacting with the community and listening to feedback is the only way Kaseya are going to build up trust. Datto does it now so there is no reason you can’t.

The People

Datto has some truly awesome people who I interact with regularly, if Kaseya are unable to keep them or make them redundant it will be a very clear indicator of which direction Kaseya has decided to take.

What gives me slight hope is that Datto is a larger company than Kaseya so there is a chance that we will get DATeya instead of KASto. I recently had a call from a new Kaseya account manager (even though we don’t have any Kaseya products until the deal completes) I outlined my concerns to them and they offered to setup a meeting with executives. Clearly as I am writing this I was ghosted by them, but the offer still stands if they want to have a conversation I am happy to! I want Kaseya to succeed and become a viable competitor in the marketplace, as more competition is good for everyone!

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