There are many misconceptions around selling Free Software, even the name is confusing, how can you sell something that is free? One of the main reasons that the term "Open Source" was coined was to simplify the message, that Free Software is more about freedom, and less about price. But it isn't as simple as that. Price matters too, especially in a struggling economy. From 2001 to 2006, I was a Sales Engineer (now known as Solutions Architects) at Red Hat, awarded Sales Engineer of the Year in 2005 and 2006. I never really planned on being in sales, it just fell in my lap, but I saw it as a problem that could be solved. In working towards solutions with each new customer, I came to appreciate and understand Free Software better. Additionally, I learned that the foundations that are widely understood and accepted in the FOSS community are very foreign to most organizations. The trick is learning how to bridge that gap, how to act as a translator. With no roadmap, no sales training, only a hacker mindset and a passion for free software, I learned many things about how to (and how not to) sell Free Software within organizations, large and small. I'll share some tips about how I was successful and hopefully give you some ideas.