Pros
Fleetio is an amazing company to work for because everyone is truly incredible to work with. You will not work at another company where everyone is this motivated, smart, helpful, and trusting. Everyone here is working to make the company better than it was the day before. Not to mention Fleetio is interested in developing you as an individual as well. Fleetio knows that work/life balance is really important and values their employees. Check out the website for the benefits of working here - they really are true! The most important thing to me is how open Tony is with where the company is and what the company's goals are. He is also very accessible and involved in the day to day of the company.
Cons
Fleetio is quickly growing and very fast paced. You have to enjoy having freedom to work on your own and not be micromanaged. I could see this being a con if that is not the way you are used to working, however, if you love it then it is actually a pro!