Breaking Through

Those who work in our nation’s capital are accustomed to meeting high performing executives who spend long careers honing their leadership and management skills in military service, civilian government service, or private sector executive positions. But much rarer is the executive that has successfully transitioned from one of these distinct careers to another. Why take the risk of leaving a successful career in the military to start over as a civilian in the Executive Branch? Or why leave an SES position in government service to start over as a business leader responsible for P&L?

Most would say such huge career changes are too difficult to manage, and fraught with risk. Navigating successfully through all three stovepipes in one working lifetime could be seen as nearly impossible, and it would be unthinkable to do so and then start a woman-owned, service disabled veteran-owned small business to top it all off.

Her story is one of charting her own unique career path and breaking through barriers to reach her goals, no matter how impossible the challenge might seem.

While her chronicle of daring career risks may seem crazy on paper, Mary Whitley has routinely defied convention and built a reputation as a level-headed, successful leader as a military officer, an SES at GSA, and a Senior Vice President in the private sector. She also founded Whitley Strategic Consulting with the goal of using her unique insights and experience in military, government, and industry to assist CEOs and their leadership teams in evolving and growing their firms in the Federal contracting environment. Her story is one of charting her own unique career path and breaking through barriers to reach her goals, no matter how impossible the challenge might seem. As a high school senior in the mid-1970’s, Mary dreamed of going to college to study engineering. Coming of age in the context of the women’s revolution, she had other spirited young women walking alongside her into the brave new world of traditionally male-dominated professions, but there were few female role models to follow. She could see her dream through the glass ceiling above her—now all she needed to do was break through.

Mary was the oldest of four children in a family of modest means, and while her parents could offer her room and board support if she worked, lived at home, and attended the local community college, she knew she’d have to make her own way if she wanted more. Despite her good grades, she struggled to piece together the scholarship funding she needed to make it a reality. “I had no connections, but given my college aptitude test scores, I had this strong feeling that I would figure out a way to make it work,” she recalls today. That’s when she received a postcard in the mail. In an extremely controversial move, President Ford had signed legislation in 1975 requiring military academies to begin admitting women. In 1976, as Mary prepared to graduate high school, those academies began actively searching for qualified women to join their ranks. The postcard she received pointed to her strong standardized test scores and academic record and invited her to apply for a full scholarship to West Point. Without telling her parents, she signed the bottom of the card and mailed it back to launch the process that would forever change her life.

Mary didn’t know anything about the military, but she knew the U.S. Military Academy at West Point had a first-class engineering school. She applied, passed a physical, and interviewed with a local West Pointer. She succeeded in securing the required appointment from a Member of Congress. When she was accepted, she knew it was an opportunity she had to take, and a glass Profiles in Success: Inspiration from Executive Leaders in the Washington D.C. Area ceiling she had to break. With that, she joined 119 other young women in West Point’s first-ever coed class

“It was a life-defining experience to have my father tell me he couldn’t help me with college, and that I’d have to do it on my own,”

she reflects today.

“It gave me the motivation to go after difficult goals and the drive to actually achieve them. It really solidified this attitude I’ve had my whole life, that I can take risks and go after goals that other people don’t think I can achieve successfully.”

The journey, however, had just begun. When she arrived to start classes that fall, it was the first time Mary had set foot on the campus. She thought the rigorous coursework would be her biggest concern. “Looking back, we women were all extremely naïve about how hard it would be,” she says. “The Academy had spent years trying to bar women from their community, and from the very first day, we were told we shouldn’t be there. The professors, administration, and older students all made their opposition very clear, and in time, even many of our own male classmates began to develop that same attitude.”

Many of the individuals entrusted with their training were the very same people who dedicated themselves to getting rid of the new female plebes within the first eight weeks of Beast Barracks. Through marching, physical fitness, Army training, and tests of discipline, the boot camp phase is designed to break new cadets down and then build them back up. Instead, the young women faced unrelenting hostility that continued into the academic year, and many dropped out in the first year. “Those of us left were excited to get past our plebe year and be accepted onto the team,” she remembers. “But that only happened for our male classmates. For us, the harassment continued. Most West Pointers didn’t think women should be in engineering, let alone in the Army, but I decided to dig in my heels. I was going to make it to graduation, whatever it took.”

Through those years, Mary remembers kindnesses made all the more special by the hardship. When the cadet companies were reorganized, and she was discouraged from socializing with her original company, the friends found ways to see each other and still share a close bond to this day. And Colonel Barney Forsythe, her assigned mentor, encouraged her along the way, promising that it would be better once she got into the Army. “Going through those hard experiences broke that glass ceiling for others, and I’m grateful that I could make that contribution to the careers of women who came after me,” she says. “But it was not easy.”

Now the founder and CEO of Whitley Strategic Consulting, an independent and experienced voice guiding Federal IT companies as they transition from small to mid-size businesses, Mary has dedicated her work to helping others break through whatever ceilings are barriers to their success. “Many businesses in that space have grown from small-business set-asides and have only vague plans for how they’re going to transition into a mid-size company that has to compete with the big boys,” she explains. “Some haven’t thought beyond a year. Based upon my experience in leading both Federal acquisition and commercial operations, I’m able to counsel them through that process, helping them consider options and strategize five years down the road. This not only creates successful companies—it creates successful CEOs with the leadership, management skills, and vision to see their companies through to a new era.”

Mary launched her company in 2007 with the intention of doing part-time strategic consulting at the intersection of government, military, and commercial federal IT. She had just left a full-time job to have a double hip replacement and planned to limit herself to only part-time work, but she soon ditched that idea to accept a full-time position with ICF International until June of 2016. She has now refocused on Whitley Strategic Consulting with the goal of helping companies grow smartly, smoothly, and sustainably. “Over the years, I’ve met so many companies with hockey stick trajectories that come to an abrupt halt when they reach the end of their small business set-aside period,” she explains. “They have the right people, projects, and contracts, but they’re unable to design and execute a strategy that enables them to continue a successful growth trajectory. That’s where I can add value.”

Mary’s own trajectory didn’t exactly follow the route she anticipated, but in breaking through barrier after barrier, she’s charted a course that is all her own. Born in the suburbs of Detroit, Mary and her siblings all followed in the footsteps of their father, a mechanical engineer. He had met their mother while getting his degree at the University of Detroit on the GI Bill after serving in the Korean War, and the young couple was thrilled when he landed a coveted job at Ford. But things didn’t go exactly as planned, and he was laid off while they were expecting their third child. He took a position with Whirlpool Appliances, prompting a move to the other side of the state. There, in a small town of 12,000 people called St. Joseph, Mary grew up.

Mary remembers having fun with the other children in the neighborhood, running around outside in the summers and playing cards or reading novels in the winters. Her family was Catholic, attending church regularly and volunteering often. Her mother was a successful substitute teacher and homemaker, while her father was deeply connected to the veteran community, instilling in her a strong love of country and service. He was also a sportsman who taught his children how to shoot early in life—a skill that helped her get into West Point later on. “My parents taught us the importance of working toward goals, whether they were schoolwork objectives or goals you set for your family or community,” she recalls. “They were great examples for me.”

Mary started babysitting at the age of thirteen and was a Girl Scout until she was sixteen. A tall, skinny girl, she could never find clothes that fit her, so she took to making her own. By the time she was in high school she made most of her own clothes, winning 4-H awards for her outfits and talent. She was friends with a great many classmates, defying social norms that suggested she had to choose a clique. She worked part time at fast food restaurants, was co-editor of the school newspaper, played the guitar, and ran track. “Title IX wasn’t passed until 1974 and the school didn’t allocate any money to girls’ sports,” she says. “Track was our only option, because it didn’t cost anything.”

Computers were just coming into workplaces as Mary entered high school, and she hoped to pursue college at Michigan State to study computer science. She always knew she wanted to have options in life, and that good grades were the key to opening doors. She was especially strong in math, science, and English, and when she took the SAT and ACT, she landed in the top one percent. “I took all two of the advanced courses available at my school,” she laughs. “By the time I got to college I thought I was pretty competitive, both academically and athletically, but it turned out I was a big fish in a small pond, and that high schools on the East Coast were operating on an entirely different level.”

At West Point, Mary encountered peers who had played softball, competed on diving teams, and run marathons. Despite the unique challenges of her situation, she focused on the institution’s unparalleled curriculum in leadership, strategy, and engineering. In 1980, she became one of the first 62 women to graduate from West Point—an incredible achievement that took courage and tenacity. “It was the hardest thing I’ve ever had to do,” she says. “But I definitely benefitted from the experience I had there.”

Upon graduation from West Point, Mary became one of five woman officers at the 24th Infantry Division, at a 15,000-person post. There, serving as the 2nd Lieutenant Platoon Leader of 45 truck drivers at Fort Stewart, Georgia, she found she enjoyed the work. “I came from a family of people who built cars,” she says. “I liked the trucks and the truck drivers, and 30 percent of my 45- person team were women. I had never before met women sergeants, and I was accepted as part of the team from Day 1. For the first time, nobody was questioning why I was there.”

With that acceptance, Mary could finally be the person she wanted to be, honing her management skills—especially in working with noncommissioned officers who were adjusting to life after the Vietnam War. She volunteered to be the Battalion Motor Officer, so she was sent to school at Fort Knox to learn more about heavy duty vehicle recovery and maintenance. In that class, she met Lieutenant Roy Whitley, the man she would later marry in 1985.

Mary and Roy were reassigned to Germany, where she served in the 4th Transportation Command and 590th Trans Co overseeing long-haul trucks and a truck company of over 200 people. “It was the mid-80’s, and we were preparing to defend Germany against the Eastern European invasion that never came,” she says. “I learned a lot about leadership and management there at a very visceral level, but I wanted to navigate into IT. I decided to take night courses at Ramstein Air Force Base to get my master’s degree from the University of Southern California.” She completed the Systems Management degree with an IT focus in December of 1985 and applied to become a Logistics Automation IT Manager at the Pentagon.

During her four years in that capacity, Mary had two children and was assigned to both the Army and Joint Staffs. She then went to Fort Belvoir, where she worked as a Product Manager of tactical logistics automation during the First Gulf War. Then, after serving eleven years of active duty as an officer, she entered civilian life and took a GS-13 job at General Services Administration managing Federal IT acquisitions. “Although my military friends and mentors advised me not to resign my commission and move to GSA, that turned out to be another great job,” she reflects. “I was hired and helped through military to civilian transition by Rick Davis and worked for the Federal Systems Integration and Management Center, which handles the most complex IT procurements for all of the federal government, with a particular focus on the Department of Defense.”

Thanks to her ten years of previous management experience, Mary was promoted after only one year. The organization had one GS-15 woman who was running the software division, and when she decided to retire, Mary was selected for another promotion. “It was a meritocracy and a wonderful place to work, but all of the deputies to the division leaders were women, while all of the leaders of the division were men—except for me,” she says. “I eventually became the deputy to my mentor, Charlie Self, the IT Solutions Assistant Commissioner at the next level up, when we were responsible for over $1 billion in federal procurement per year. Through my position there, I was able to mentor other talented men and women to be promoted to leadership positions.”

Several years later, at the age of 42, Mary landed a Senior Executive Service position, breaking another glass ceiling a good six years before she could have attained an equivalent position of General Officer in the military. Responsible for CRM and Sales, she set to work creating an entirely new protocol for GSA based on industry principles, and installed the first industry standard CRM system in the Federal government. “We ended up training many government employees in customer relationship management and sales methodologies on that platform, and they really took to it,” she recalls. “It helped get everyone on the same page in their thinking about obtaining and retaining customers.”

Four years later, Mary decided she was ready to go to the private sector. With that, she wrapped up 27 impressive years in public service and took a VP job at Unisys Corporation, a Federal IT service provider. Again, she found herself in a male-dominated environment, but also found a great mentor. “I knew about contracts and IT services management, but had to learn pricing and how to manage the P&L,” she remembers. “Drew Cramer’s business mentorship was incredibly important to me as I managed an operational group of over 300 people in multiple locations across the nation and in Europe. I refer to it as my time in the salt mine—I was there when the doors opened in the morning and closed at night, trying to absorb everything I could.”

After two years in that capacity, Mary transitioned to MAXIMUS, a professional services company specializing in implementing government health and human services programs that allowed her to pursue her interest in Health IT. “I felt that big changes and exciting innovations were going to be taking place in that space,” she explains. She was charged with growing a small 8(a) company acquisition into a larger information security offering, but a few years later, the MAXIMUS CEO and leadership team determined that the Security Management Division did not fit well into their evolving strategic plan. Mary knew the Division had valuable customers and trained team members, so she worked to spin off that business unit through its sale to a West Coast biometric engineering firm. “It was a good transaction for both companies—and my first time leading an M&A,” she says.

After launching WSC, Mary landed a Senior VP position at ICF working for her friend and mentor, Ellen Glover, who set her at the helm of a brand-new division created through the purchase of an 8(a) firm of aggregated HHS services. “The Division lacked a mission statement and a unifying strategy, so I worked with the team to formulate the Health Informatics Division Strategy, which combined IT, information science, and health program expertise to support HHS’s missions,” she says. The “health informatics” route proved hugely successful, growing the initial group from $28 million to $80 million in revenues. She was then asked to integrate and lead a new division which came to fruition during a 9-month project to create three business lines involving IT, programs, and research. Once that process was complete, she decided to strike out on her own under the Whitley banner to focus on her most lasting legacy.

Parallel and integrated with her professional success, Mary has been happily married since age 27, and is the mother of two adult children who have made successful careers for themselves in cybersecurity and health informatics. “I decided early on that I was going to be a working mother and wife, and I never wavered in that,” she says. “When I entered the service, very few women in the military were also wives and mothers, so making that choice was a seminal moment for me. Roy has always been incredibly supportive—a self-made man, a loving father and husband, and a great leader. We’ve both found ways to have very full professional lives through being true partners to each other and a solid team, pulling off the balance between family and successful careers.”

Now, as a leader, Mary’s philosophy evolves around the belief that people and organizations evolve. Seeing change as an inevitability that can be channeled in a positive or negative manner, she embraces the power of mentoring as a force to enable positive evolution, as notable people did for her as she, herself, evolved. “All along the way, I’ve had mentors who have helped me, showing me how to make good decisions and be a strategic thinker,” Mary recounts. “Through WSC, I want to be that mentor to other business leaders, and also to help accomplished women in the DC metropolitan area who desire to serve on boards. In fact, I’ve recently begun collecting resumes to do just that.”

In advising young people entering the working world today, Mary underscores the importance of the first step. “After you’ve decided what you’re ultimately aiming for, set your sights on that first job that will get your foot in the door so you can start learning,” she says. “It might not be the career you want right away, but it’s a place to start. Chart your own path, even if others like you haven’t walked that way before. If you believe it’s the road that will lead you to the right place, be courageous and tenacious and don’t listen to the people who say you can’t do it. Where there’s change, there is opportunity, so break through and find out what comes next.”

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