Rebecca Wynn has always had an affinity for education. She breezed through high school in two years and started college early, heading to Cal Poly San Luis Obispo. She initially entered a science program, but switched into the Art and Design Photography program to put her love of photography to work. After graduation, she did shoots for Sports Illustrated and other companies, and she had shows of her artwork, but it wasn’t long until she headed back to school to work toward a double MBA in Finance and Marketing, which she achieved by age 21.

Wynn began her career selling insurance and helping people with financial planning. She didn’t find those activities very exciting. What did excite her, however, was writing her own computer programs to generate customized reports for her individual and business clients, such as cost savings through self-insurance. “I liked helping people, and getting the right products for them, but I didn’t like the other stuff,” says Wynn. Considering her rekindled interest in computers, she went back to school and attained a degree in Information Technology. “I excelled in programming, and as soon as I got out of school, I had several job offers waiting for me.”

She accepted a programming position at OEM Surplus, where she created custom applications to streamline operations and help the company save money. She also did development for retail companies in the U.S. and Canada, basically streamlining procedures for the companies. From there she was offered a position as an Information Security Officer for Early Warning, a technology provider to the financial services sector. “I really enjoyed that,” says Wynn. “It’s not always about looking how to improve security, but actually speaking to all the business owners and getting to know what is important to them.”

Wynn then went on to spend six years with NCI Information Systems, which is a government contractor. She had a series of progressively more responsible roles.

“I was hired as a Senior Information Security Analyst. Within three months I became an Information Security Engineer and Deputy Team Lead. And then within probably a year or so, I was a Senior Security Engineer and I was fully leading teams doing all this work. Then I became a Senior Principal Security Engineer, and eventually a Subject Matter Expert. My colleagues dubbed me a ‘One Woman Army’ because of all the projects I took on. The clients would allocate ten months to get a project done, and I would come in and get the thing done within six weeks, on time and on schedule. I had a really good name that way,” says Wynn.

Soon after, LearnVest came calling. “LearnVest takes the mystery out of financial planning and brings it down to the regular person. This was really a great opportunity for me,” says Wynn. “I started out as the VP of Security and within three months, they asked me to take over the Compliance Department, too, so I was VP of Security and Compliance. Shortly after I got there, Northwestern Mutual acquired LearnVest. I ended up taking them through their pre-acquisition phase, to the acquisition and then post-acquisition. I assumed the role of VP of Enterprise Security and Privacy for the company. I was put on the Senior Leadership Team under the Chief Information Security Officer of Northwestern Mutual.”

“I spent three years of working seven days a week, 14 hours a day, and I was just burnt,” says Wynn. “I had planned to take three months off, just to get some R & R, relax, recoup, and then see what my next chapter in my life would be. And I saw the opportunity to join Matrix Medical Network as the Senior Director of Information Security, which is really a CISO position. I just really felt that Matrix Medical was a good fit for me, not only for the company’s culture, but the way that they were processing business. We are all A-type people, but we also have work life balance, and it just seemed like it would be the right fit.”

“I’ve been very good in my life that when I’ve felt in my heart of hearts that I needed to do a change, the right opportunity has mainly come across my path within two weeks. I’ve just been very fortunate that way. So long story short, that’s how I kind of got into this business doing what I love,” says Wynn.

She has a philosophy of “always keep learning.” According to Wynn, “I think that there’s two types of people. There’s people who have a lot of education and because they have education, they don’t want to learn. And then there are people like me who, the more you know, the more you know you don’t know everything, and so you’re open to always being a life learner, and that’s where I am. I’m always trying to learn and pick up new things. It helps to keep you young, right?”

Wynn believes in working hard and playing hard. “When I’m on vacation, I’m jumping out of airplanes, I’m scuba diving, I’m ATVing. I do all the crazy things and some people say I’m nuts, but I’m an adrenaline junkie that way. But I try to do it where it’s in a safe environment, so I can have fun doing it.”

She’s also a musician. “On Tuesday nights I play in the South Mountain Latin Jazz Band. It’s the premier Latin Jazz Band in Arizona,” says Wynn. “On Wednesdays, I play in the Scottsdale Concert Band, and then I do go ahead and volunteer in two performing bands when they need me, the San Tan Orchestra and the South Mountain Day Jazz Band. I do play trombone very actively because it helps me forget about work for a few hours.”

Wynn also devotes time and resources to charity work in her community as well as abroad. “I think God has blessed me with money and resources, and I think I do have a responsibility to go ahead and pay that forward as much as I possibly can. This year I started buying land in places like Madagascar. I’ll buy acres of rain forests and that way the government and businesses can’t grab the land and resell it. This leaves the acreage pure. I’ve provided resources for African villages to build water wells and buy water rights and that sort of thing. Down in Central America, I bought plants and water rights so that locals can grow their own food. I try to see that the world is beyond me even though day-to-day, it’s easy to get caught up that it’s all about you.”