Get to know Jeannie Winchester

Jeannie Winchester, product lead for the Enterprise Business Systems – Convergence (EBS-C) program, is helping the Army converge six legacy enterprise resource planning (ERP) systems into one.

EBS-C is a new PEO EIS program that is part of the Army's Enterprise Business System Multi-Functional Capabilities Team (EBS-MCFT), a coalition established to plan and implement the Army’s ERP modernization effort. Over the coming years, the EBS-MFCT will develop enterprise requirements for a converged ERP solution. Industry can learn more about future EBS-C business opportunities at a virtual Industry Day slated for Feb. 25.

After serving in the Air Force for six years, Winchester was a defense contractor specializing in information technology infrastructure and cybersecurity for 13 years. She joined PEO EIS as a civilian in 2011 and has led cybersecurity, communications and classified projects. A West Virginia native who enjoys the outdoors, Winchester answered questions about her career, life and values.

What inspired you to join the Air Force?
After I graduated from high school, I really wanted to go to college, but my family couldn’t afford it. The military offered fantastic GI Bill benefits to pay for college.

Where did you grow up?
I grew up in Arnoldsburg, a small town in West Virginia with a strong community spirit. Everybody knows everybody. Arnoldsburg shaped my values. I was taught from a very early age not to expect something for nothing.

There isn’t a West Virginia joke that I haven't heard 100 times, but I believe West Virginia is the best-kept secret. Places like my hometown don't exist anymore. Neighbors care about each other. If someone is sick, neighbors deliver food to their home.

How do your friends describe you?
My friends describe me as hard working, dependable and transparent. You never have to worry about what I’m thinking.

What do you enjoy doing when you’re not working?
I love being outdoors and am an avid paddle-boarder. If I am really wound up, I grab my paddleboard and head to the water. If I really want to be frustrated, I grab my golf clubs and head to the course. [Laughs.]

When are you happiest?
At work, I am happiest when I am being challenged. I love to solve problems. At home, I am happiest when I am hanging out with my family and friends. It really grounds me. I spend a lot of time with my two dogs — beautiful little creatures with great personalities.

Why have you been successful in your career?
There’s no secret formula. I just work really hard and am very mission focused. I keep people at the forefront of my head. A happy team is a productive team. I have been successful developing and running well-oiled teams that meet the mission objective.

I have diverse experience. I have been active duty, a contractor and a government employee. I never forget those perspectives. It definitely helps me understand the best way to approach system integrators because I’ve been in their shoes.

I try to not have the word “no” in my vocabulary. When there's a problem ahead, I try to figure out how to climb that mountain or navigate a way around it. At PEO EIS, you have to be flexible and willing to get out of your comfort zone. I love being put in situations where I'm uncomfortable.

What advice do you have for people just starting their careers?
Cultivate daily habits that help you stick to your goals. Figure out what direction you want to go in and try to stick to it. Don’t jump around too much.

Understand that it's okay to be assertive and ask for what you want. You have to be appropriate in the way that you do it. You don't want to be perceived as ranting or whining. 

Find a good mentor.

What challenges have you overcome?
I did a lot in backwards order. I joined the Air Force, got married and had two kids. Then I got my degree. I pursued my bachelor's degree and my master's degree with two young children while working full-time.

I think all problems are solvable. But if you want something, you have to be willing to get off your butt and do something about it. I wanted to complete my degree, so I went to school while working and raising kids.  

What does a good leader do?
Every good leader has a phenomenal support team.

A good leader listens; it’s not just hearing what other people say. I listen to my team. If I decide to go in a different direction, I let my team understand why. Communication is key.

What does a good leader not do?
A good leader does not assume they know everything. A good leader does not overestimate their own abilities. It is important to be self-aware and recognize your own strengths and weaknesses.

If you could thank one person in your life, who would it be and why?
My grandfather had a big hand in raising me. He only had an eighth-grade education, but was one of the smartest people I've ever known. He encouraged me to work hard and set goals. He said I could do anything I wanted to if I applied myself. I swear — every day of my life I hear him giving me advice. He's like a little angel who sits on my shoulder.