Board of Trustees

Eileen is Senior Vice President and Capital Region Managing Director of Alliant Employee Benefits, where she aids organizations in designing and managing health care and employee benefit programs and risk strategies. She has over 20 years' experience in the field of health strategy, employee engagement, and workforce health and productivity. Eileen has a B.A. in Psychology and Economics from St. John Fisher College in her hometown of Rochester, New York. She has three children: Max ’12, Mia '22, and William '24. She resides in Warrenton with her children and husband Steve Penders.

Piers is the Founder and Chief Executive Officer of Teneo, a Specialist Integrator of Next Generation Technology who focus on Networking and Security for Enterprise customers around the globe. He was educated in the United Kingdom at Reading University and holds a B.A. degree with honors in Geography and English. Piers has two children: Joshua, Class of '21, and Sophia, '22, Piers is married to Amber and they reside in Middleburg, Va.

Dr. David Bassam is a native of Northern Virginia having grown up in Alexandria and graduating from Virginia Tech (B.S. 1993) and The University of Virginia (M.D. 1997). Dr. Bassam is the principle founding partner of a specialty medical practice focused on the care of spine conditions in Manassas, Virginia. Dr. Bassam’s professional interests include efforts to combat the ongoing opioid epidemic through advocacy and education.  Dr. Bassam has served on the Virginia Board of Medicine as well as other area civic organizations. Dr. Bassam sponsors rising Wakefield seniors interested in pursuing medicine with summer internship opportunities through the Wise program.  He and his wife Laura are strong advocates for independent schools and active members of the Wakefield community. Dr. Bassam has four children at Wakefield (graduating classes of 2026, 2027, 2029, and 2031) who have been enrolled since JK.

Karen's professional background focused on real estate development, urban planning and revitalization, and environmental issues, both as an urban planner and thereafter, a lawyer. She has always had a strong commitment to pro bono activities and enhancing the lives and infrastructure in urban and rural communities. After a ten year tenure with law firm DLA Piper in Chicago, her family moved to Virginia in 2007. She has her own Virginia pro bono practice serving those in our larger community to find creative solutions to legal problems.

Karen Way has one son and is Godmother to three Wakefield students. In addition to spending time with her husband and son, she is known for her friendly cows and leading hiking adventures around her family's farm, Ovoka in Paris, Va.

Kevin has been in the construction industry for more than 30 years, working as an engineer initially, then serving an apprenticeship and working his way up to CEO of an electrical contracting company. He now works for a national electrical contracting company managing preconstruction in the DC Metro area. He is also active in various industry associations, serving on the boards of the Associated Builders and Contractors, and the Prince William County Education Foundation (CTE component).

He is also very active with various children's charities, including the Rainbow Therapeutic Riding Center, and serves on the board of directors of Youth For Tomorrow, a charity serving at-risk youth in a residential educational facility, in outpatient facilities, and with foster care programs throughout Northern Virginia.

Kevin and his wife, Karen, have three children, all of whom are Wakefield graduates: Rachel '11, Hannah '16, and Jared '18. Rachel graduated from American University. Hannah graduated from James Madison University and is now working on her second BS degree at Shenandoah University. Jared attends Old dominion University.

Mr. Cowasjee is currently responsible for the development, design and construction of the Washington, DC, Chicago and Boston portfolios. Since joining Tishman Speyer in 1999, he has been responsible for the design and construction of the company’s projects in Northern Virginia, District of Columbia, Chicago, Philadelphia and Boston. He has also been responsible for setting up Tishman Speyer’s design and construction departments and projects in India. Prior to joining Tishman Speyer, Mr. Cowasjee worked for London & Leeds Development Corporation and was responsible for the design and construction of the commercial office building portfolio and hotels in the Americans, including in Canada, the Caribbean and South America. He has also worked as an architect for I.M. Pei & Partners in New York. Mr. Cowasjee graduated from Cornell University with a B. Arch and earned an MAUD in architecture and urban design from the Graduate School of Design at Harvard University.

John joined Wakefield's Board of Trustees in June 2004. John served in the Air Force for 35 years where he had extensive combat and Pentagon-level assignments. Upon retirement in 1997, John worked for DynCorp and the Computer Science Corporation. For the past ten years, he has served as the Director of IBM's Strategic Business Relationships Team. He holds a Bachelor's degree in Social Sciences from San Francisco State University and has advanced studies at Harvard University and the Massachusetts Institute of Technology.

John served as a Trustee from 2004 to 2016, when he became a Trustee Emeritus He rejoined as a Trustee in May 2020.

John and his wife, Donna, have one daughter, Kelsey, and one granddaughter, Mariah '13.

Ashley Harper is Head of School at Wakefield School. Ashley's career in education spans teaching, college admissions, lower and middle-school division leadership, and development. Ashley has a B.A. in Economics from Florida State University, and a M.A. in Teaching and Learning/Curriculum and Instruction from Nova Southeastern University in Fort Lauderdale, Florida. She was a National Association of Independent Schools Aspiring School Heads Fellow from 2011-2012.

Ashley and her husband, Doug, have two children: Jack and Riley (Class of 2024).

Kevin joined Wakefield’s Board of Trustees in 2013. Kevin is a Certified Financial Planner, and the owner of Handford Financial Strategies, a financial management firm. He is a graduate of the Virginia Military Institute with a degree in Economics. He is a strong believer in small schools such as VMI and Wakefield School, and the community and networking that can be fostered in such an environment.

Kevin and his wife, Jennifer, have three daughters: Gabriella and Brianna, Class of 2020, and Natalie, Class of 2025 . The Handford family has been at Wakefield for eleven years.

Stamatina McGrath was elected to the Wakefield Board of Trustees in 2018. Stamatina earned her B.A. in History at The College of William and Mary, and both her M.A. and PhD (Byzantine History) at The Catholic University of America. She teaches History at George Mason University. Dr. McGrath is very active in the Wakefield community and looks forward to continuing to help improve the educational experience for all students.

She and her husband Jim have two children: Nicholas '17, and Anna, Class of 2021. The McGrath’s have lived in the Centreville area for the last twenty-six years.

Darrin is the Owner/Founder of Beverly Equestrian. She was instrumental in bringing together an Equestrian Program at Wakefield School and serves as Co-Chair for the Great Meadow Eventing Committee. Darrin is an attorney and has worked in the field of litigation with an emphasis on employment and intellectual property law. Darrin holds a B.A. and J.D. from the University of California, Los Angeles.

She and her husband, Bill Ballhaus, have two children: Brooke, Class of 2022, and William, Class of 2025.

John is a partner at Akre Capital Management in Middleburg, Va. Prior to coming to this area, John worked for William Blair & Company in their equity research department. He holds a B.A. in English from Colgate University and a M.B.A. from the University of Chicago. John and his wife, Jennifer, have two children: Michael , Class of 2020, and Kate, Class of 2023.

Linda is Senior Managing Director for Government Relations and Legislative Affairs for CME Group, a global derivatives firm based in Chicago. She is responsible for developing and implementing CME Group’s U.S. and global legislative and policy strategy. Linda has also worked as head of government relations for the NYSE, and prior to that, on Capitol Hill as a Senior Counsel to the U.S. House of Representatives Committee on Financial Services. She holds an A.B. from Brown University and a J.D. from George Washington University.

She and her husband, Peter, have three children: Mackie '18, and Will and Walker, Class of 2021.

Susan Whitson and her husband, Keir, are parents to son Dryden (grade 4) and daughter Lucy (grade 2). They live in Washington, Virginia. in Rappahannock County.

Susan is co-founder and co-owner of King & Whitson Travel, a boutique travel agency that designs unique itineraries filled with enriching, off-the-beaten path experiences, coupled with personal service. Susan and her business partner, Martha King, have been named as Conde Nast Traveler magazine's 2020 Top Travel Specialists in the world. Susan has traveled to more than 70 countries on six continents, and to 49 US states. (Nebraska still eludes her.)

Prior to starting her travel business, Susan served as White House Press Secretary to First Lady Laura Bush from 2005 - 2007. During her time at the White House, Susan was the chief communications advisor and spokesperson for Mrs. Bush and the issues she worked on, including literacy and education, international women's issues, and historic preservation, as well as all White House social functions.

After leaving the White House, Susan worked with HarperCollins Publisher as a media consultant and traveling publicist to promote Jenna Bush's first book, Ana's Story: A Journey of Hope, a nonfiction story about a teenage single mother from South America living with HIV.

Prior to working at the White House, Susan was the Deputy Communications Director for the Bush-Cheney 2004 campaign, where she was the spokesperson to Miss Barbara Bush and Miss Jenna Bush, the President and Mrs. Bush's daughters. Before joining the Bush-Cheney campaign, Susan was the Chief of the FBI's National Press Office and was the national spokesperson for the FBI and then-Director Robert Mueller.

From 2001-2002, Susan was the Deputy Director of the Office of Public Affairs at the U.S. Department of Justice, where she served as the deputy spokesperson for then-Attorney General John Ashcroft on national breaking news, including the Sept. 11, 2001 terrorist attacks.

From 1997-2001, Susan served as a press secretary on Capitol Hill to Rep. Bob Riley of Alabama and Rep. Bill McCollum of Florida.

Susan began her career as a high school English teacher at Hoover High School in Hoover, Alabama. Her most famous student is Taylor Hicks, the 2005 winner of American Idol.

Susan holds a bachelor's degree in Secondary Education Language Arts from Auburn University in Auburn, Alabama.