Advice for Fellow Executives

CF: Executives at different stages of their career go to work for other firms – build, leave, go off and do other things – and it gives them a moment to reflect on what they want to do. You left Datto after a stellar ride, and you had a little bit of an intermission before announcing the Pax8 position. Can you take us through some of your thoughts on that process? Is there anything that might help execs in similar positions?

RR: It’s funny you say that, because there was a rumor out there that I was actually retiring and opening up a chicken restaurant.

I’m like every other human being; I’m averse to change. However, I’ve also learned in my career that the longer you stand still, the slower your growth becomes. So for me, I compare it to when you buy your first house. You loved it, it was a memorable moment. But as much as you love it, you wish it had another bedroom, a finished basement, whatever the case may be. And I think in job hunting through this, I kind of did that same thing. I loved my time with Datto. It was a spectacular time for me and the people that I engaged with and all the people that I got an opportunity and privilege to work with. But then you tick off all the things that you love about it. And then you also tick off the things that are potentially missing, or that you want in that next career step. Taking some time, I was able to step back and look at all the things that I wanted that were potentially missing, or all the things that I wanted in, in a new job.

I made that list, and then just tried to find the best fits for each of those different things I wanted for myself. It’s not just a paycheck. It’s not just equity. It’s about things like the relationship like the community, the ecosystem, culture, workplace, executive team.