Exemplifying grit, grace and gumption

Alum’s post-military and post-Microsoft career includes adventure, entrepreneurship

Photo courtesy of Lee Christofferson

Microsoft alum Sheryl Tullis is a West Point grad and former captain in the U.S. Army who helps other veterans transition from the military to civilian jobs in tech, mentors women leaders, and is the co-founder of The Line Bike Experience.

By Susan Cameron

Meeting Sheryl Tullis is like encountering a force of nature — a leader, adventurer, and mentor who redefines boldness in every role she undertakes. Her journey spans the military, corporate leadership, and entrepreneurial ventures, each chapter shaped by resilience and a commitment to empowering others to embrace challenges and be bold.

While a student at the United States Military Academy at West Point, Sheryl was the speechwriter for retired Gen. Colin Powell. When she graduated, she served as a captain for five years. Among her leadership roles at Microsoft, Sheryl was chief of staff and speechwriter for Mich Mathews, Chief Marketing Officer at the time. She now helps other veterans transition from the military to civilian jobs in tech, coaches women executives, keeps checking off bold adventures, and is the co-founder of a business that makes cycling accessible to anyone.

Standing on the shoulders of giants

Being among the 10th class of women to graduate from West Point meant Sheryl was part of a pioneering movement. Women were being integrated, but there were still some growing pains while she was there.

“There were definitely giants on whose shoulders we stood,” Sheryl said, “but it was a decade of transformation in figuring out how women existed at the academies and how everything had to change.”

At the time in the late ‘80s, women were merely 10% of the cadet corps. Since then, the percentage has more than doubled — which is a direct reflection of the number of roles that are available for women as officers once they graduate.

West Point’s approach to education emphasizes a holistic, transformational development process that builds skills, maturity, judgement, values and character.

“We had a lot of leadership classes and training, military duties and responsibilities and athletic responsibilities,” Sheryl said. “So, it was kind of a whole person concept.”

Learning the art of connection from a master

As a cadet, Sheryl was given the rare honor of writing speeches for Gen. Powell — a role that taught her the power of storytelling and connection, as well as lessons in leadership. She remembers typing out his speeches on 5 x 8 cards, receiving them back marked up in red ink with Powell’s anecdotes added.

“He was really masterful in the way he would make his stories fit and connect with whoever the audience was — the Rotary Club, a graduating class, high ranking officers — and he was able to connect with every single one of them,” she said. “He inspired me in so many ways.”

Powell invited Sheryl to join him on a trip to deliver speeches at military bases around the country. They travelled with Powell’s high-ranking staff on a military aircraft a bit smaller than Air Force One, complete with a personal chef.

It was her comment about a billboard she saw on that trip that removed barriers and deepened their relationship. The billboard said, “Tattoos while you wait,” to which she responded, “What other kinds are there?!” She later wrote about this story, lessons, and the lasting impact from her summer with Powell in a blog, “Horses > Generals and other lessons I learned from Colin Powell.”

“He was very interested in his people, you know, personally,” Sheryl said. “He dug into my background on that trip.”

Sheryl shared with Powell that she was thinking about going into information systems and communications, which was the Signal Corps branch of the United States Army. “He really validated my choice of career path,” she said, “and he also encouraged me to be the best communicator I could be.”

Photo courtesy of Sheryl Tullis

While at West Point, Sheryl was a Cadet Captain. She reached Army Captain later in her career.

Leading with resilience

After graduating with an engineering degree, Sheryl went on to be a captain in the U.S. Army. During her five years of service, she led a 120-member unit which provided secure information management systems and communications services to seven military communities throughout Germany.

The leadership foundation Sheryl built as a cadet and during her service carried through to her roles at Microsoft and beyond, and she has evolved her approach to adapt to current times.

Sheryl reflects on the concept of “VUCA” — volatility, uncertainty, complexity, and ambiguity —which was introduced in the post-Cold War era by the U.S. Army War College while she was a cadet at West Point.

“Today, with the world feeling like it’s becoming increasingly complex,” Sheryl said, “leaders need a model for operating in a VUCA framework.” As she was writing an article, she learned about a new concept called VUCA Prime — vision, understanding, clarity, and agility — which she uses today in coaching women and veterans to help them be resilient, bold leaders in today’s VUCA world.

Creating pathways for veterans

“I've always tried to help veterans transition,” said Sheryl “because it's a pretty murky world in figuring out how to apply [military] skills.”

Not everyone leaving the military has directly translatable skills, so Sheryl has helped veterans translate their skills to prepare for civilian jobs, network with business folks, and learn the language of business.

Post-Microsoft, while Sheryl was a partner at Direct Technology, she worked with the Microsoft Military Team to pioneer Microsoft Software and Systems Academy, the first DOD high-tech transition program for veterans leaving military service.

Today, Sheryl continues to mentor and coach veterans both formally and informally. She helps them explore opportunities, update their resumes to be relevant for civilian jobs, prepare for interviews and, as she puts it, “break the ‘we’ to talk about what they specifically did to change things and to leave things better than they found them.”

Boldly seeking adventure

“It's that moment before you take the leap that is scariest part,” Sheryl said. “Once you do, it inspires confidence — confidence that you can do it again.”

Sheryl grew up with a love of the outdoors and was always encouraged to try new things. Adventuring offers endless opportunities to push boundaries and build confidence. The year before Sheryl turned 50, she set a goal to do 50 new adventures, and she ended up doing more than 80, redefining what boldness means at any age.

“Just to get out of my comfort zone, and I guess convince myself that I wasn't really old,” she said, “And what that taught me was sometimes you just have to say you're going to do it, and those opportunities come to you.”

Sheryl paraglided, summited Mount Rainier, went to concerts with music she normally wouldn’t listen to, tried new foods…the list goes on. “I love adventuring and being creative, and I love doing it with people — it's a real chance to build stories that last.”

Blazing new trails

Recently, Sheryl added another challenge to her repertoire — mountain biking. As a former triathlete, she is a road cyclist but had not spent much time on trails...until recently.

Microsoft alum and former colleague from Sheryl’s MSN days, Mike Kunz, approached her to start a bike experience business with him and they co-founded The Line Bike Experience in 2023.

The business, based on North Bend, Washington, is more than just a venture to make biking accessible — it’s a way to “bust the barriers to mountain or gravel biking and get people out to enjoy the public lands, which their taxes pay for,” said Sheryl.

Converted from an old gas station-turned-auto repair center, The Line Bike Experience is a modern bike shop offering an experience. They have instructional courses, tell people where to ride within their ability, and provide a community so people can find riding buddies matching their skill level.

“But the real magical concept,” Sheryl said, “is that we have shipping containers of bikes that we place at trailheads, so people can rent online, show up at the trailhead and never have to own or transport a bike.”

It’s about creating opportunities for others to step outside their comfort zones. Every boundary crossed, every comfort zone stretched is a reminder to embrace life’s opportunities and challenges with courage.

As Sheryl puts it, “We only get one shot — so be bold, lead with purpose, lift others as you go, and leave the world a better place.”