Spotlight Archive - Rick Wilson

Spotlight on Rick Wilson

Rick with their daughter Rick the pilot Rick Wilson

Throughout Richard (Rick) Wilson’s career there have been a few constants; exploration, risk and aviation. He started his formal career working for a small jet manufacturing company in Nevada. Then he moved to Chicago to work for United Airlines before starting his own consulting firm. About 18 years ago he moved his software development company to Connecticut, where he expected to stay for “4-5 years” but seems to have found some degree of permanence. 

When you meet him, you realize he’s an uncommon person – so it’s no surprise he holds an uncommon job title to match. Rick is the Chief Transformation Officer at SphereGen Technologies in New Haven Connecticut. When asked the common question “What brought you to this role?” Rick had the following to say: 

“I had been working for a consulting firm that grew quite large. When I was considering leaving, I evaluated what I genuinely enjoyed doing. Part of my desire to leave was the slower pace of innovation larger companies tend to have. So, I looked to transition back toward a smaller company where change is easier to implement.
Larger companies just are not as nimble as smaller companies. Companies which have thousands of employees need changes to be planned out in advance and rolled out slowly. They are like passenger jets, no abrupt movement. I desired a better balance between tactical and strategic. I wanted to get back to being able to assess problems quickly, make decisions with a few people, and then implement what we decide upon. I was looking to get out of an airliner and be back in a fighter jet for a while.
When I talked with the owners of SphereGen, we clicked on a lot of levels. We laid out a strategy of focusing on our mutual passion to transform client businesses using technology and their desire to transform their own business. Transformation was the main goal, so that’s how we decided on the title.”


Rick’s career has had a strong entrepreneurial streak with more than half of his time spent in an ownership role or as an independent consultant. He feels any job he has held, always provided a way to learn a new skill. As an example, in college he knew he wanted to get better at public speaking but “couldn’t see paying for a semester of class to learn it.” So, he convinced the owner of the bar where he was working, to make him MC for the comedy club upstairs. “You learn how to manage a crowd quickly when your audience is a bunch of out of control college kids.” 

I then asked him about what it was like to run his own company and the challenges he faced. 

“The transition from an independent contractor to having employees was a hard one for me. As a contractor, I had a high-risk tolerance because I understood and accepted the consequences of picking the wrong client or project. Once I had employees my choices impacted others. My risk tolerance had a direct impact on people who I was responsible for. It took some time to the balance between being overly cautious and what level of risk was acceptable to expose others to; and to have the confidence to know the difference.
But above all that, the hardest part was letting go of control. Learning how to focus on the end result of the work of others, not how they got there. THAT was REALLY hard. But once I learned that concept, I witnessed the strength that it brings to an organization and how it allows growth in ways I couldn’t have imagined.
That’s when there is this great feedback loop of leading and learning. Where it isn’t just about leading a team or a company but learning from them as well. With the right group, and the willingness to change, it’s one of the best things ever.”

Rick is a relative newcomer to SIM, having joined less than a year ago. He was drawn in by the caliber of members and the palpable desire of participants to actively participate in sharing their knowledge and helping others grow. 

On a personal side, Rick was born in the Midwest, and is a graduate of the University of Missouri with degrees in Mathematics and Physics. The last child of a very large family, he has lived across the U.S. and has a passion for travel that grew during his early career. He has traveled to almost 30 countries and has been to every state in the U.S. 

When Rick isn’t working, he enjoys time with his wife of 26 years, Monica, and their 17-year-old daughter, Sabina. Additionally, he has a personal volunteer project which is helping veterans on the brink of homelessness. He has a passion for learning new skills. He indulges a lifelong interest in aviation and has been a private pilot for almost 20 years. Recently he has been training to gain a helicopter rating. As he puts it, “an exercise where I have the quickest feedback loop possible for my mistakes. It’s a great exercise in humility, perseverance and control. I absolutely love it.” 

Written in collaboration with Montos Vakirtzis and Beverly Lieberman