The Board of Trustees is a dedicated group of volunteers committed to the mission and philosophy of the school and has three main responsibilities:
- To sustain the school’s mission and program
- To maintain the campus and facilities necessary to carry out the program
- To secure the funding for the program to be successfully implemented and for the campus and facilities to be well maintained
The full Board meets six times per year. Each member participates on at least one standing committee. The committees include: Alumni Association, Buildings and Grounds, Development, Education and School Life, Executive, Finance and Endowment, and Parent-Teacher Club.
Board of Trustees
Mr. Michael H. Howland
President
Michael Howland (“Mike”) is a retired career diplomat and CEO. Mike began his 35-year public service career in the military and is a decorated Vietnam veteran. Mike followed his public service career by founding a national security consulting & technology services firm. Retiring in 2018, Mike is presently writing a book drawn from a secret journal he kept while being held hostage in Iran from 1979-1981. Mike is a frequent speaker on the Middle Eastern & Central Asian affairs, the Iran Hostage Crisis and radical Islam.
Mike is an avid fly fisherman and chases wild trout, with moderate success, anywhere he can find them. Fun fact: Mike is a collector of rare travel diaries from 19th century Central Asia and India.
Mike lives in Upperville, VA with his wife Kathy and their English setters. Kathy’s son Keenan Jackson ‘02 is a proud graduate of the Hill School.
Mr. Michael H. Howland
President
Board of Trustees
Mr. Erich Weber
Vice-President
Erich has lived most of his adult life in Northern Virginia after leaving his boyhood home in the Los Angeles, CA area for Georgetown University in Washington, DC. Early in his career he worked in a series of operations-management roles in the Department of Justice while eventually earning his MBA in night-school at the University of Maryland, College Park. He soon helped to start Kelley Management Consulting — and after 15 years with KMC he still enjoys the work, his colleagues, and his clients. Erich met his wife Rachel at GU and they moved progressively west as their family grew. They now live in Leesburg, VA where they have two sons (Ethan, Hill ’16 and Woodberry Forest ’20, and Andrew, Hill ’19). When he’s not working on the next interesting client challenge, he’s most likely reconnecting with Rachel in the bleachers or on the sidelines – and sometimes even at a Loudoun winery. Erich enjoys golf, skiing, and being outdoors, and looks forward to getting to know and work with the next generation of Hill School families.
Mr. Erich Weber
Vice-President
Board of Trustees
Mr. Charles M. Ellison ’97
Treasurer
Charles, who graduated from Hill School in 1997, has been a member of the Alumni Association Board since 2007 and was president from 2011 through 2014. Charles graduated from St. Andrew’s School in Middletown, DE in 2001 and from Tulane University in 2005 with a BA in Political Science. He, his wife Jennifer, and their four young children Sterling, Hazel Mae, Opal, and Elvy live in Winchester, VA.
Mr. Charles M. Ellison ’97
Treasurer
Board of Trustees
Mrs. Angela Killinger
Angela was born and raised in Northern Va. She received her under graduate degree from the University of Colorado and went on to get her Masters degree from Johns Hopkins. Currently Angela is the General Manager and Vice President of Joyce Koons Honda Buick GMC. She is third generation automobile dealer, following in the footsteps of her grandfather and mother. She believes buying a car should be a joyful experience and her life motto is to hustle kindness. Angela is a member of NADA (National Automobile Dealers Association). Outside of work she acts as an advocate in the community for children with cancer and has a partnership with Journey 4A Cure, KEEN (Kids Enjoying Exercise Now) and SPARK (Prince Williams County’s Education Foundation). Angela is a mother of four Hill School students, Ellie Rose (Hill ’18), Chloe (Hill ’19), Lilly (Hill’22) and Keagan (Hill ’24). She loves spending time with her children, visiting with friends and creating new things with her sewing machine.
Mrs. Angela Killinger
Secretary
Board of Trustees
Mrs. Annie Bishop ’94
Annie was born and raised in Middleburg. Annie was lucky to be a part of Hill School Class of 1994. After Hill, Annie attended Foxcroft School (‘98) and then Lynchburg College, where she studied communications. Annie spent 10 years in DC working at The Glover Park Group where she was responsible for the creative and production of integrated campaigns for clients ranging from large brands to non-profit and advocacy groups. She is currently the co-founder and a managing partner of ZEBRA NYC, a creative and production company based in NYC. Annie was happy to join the Hill School Alumni Association Board in 2010. Annie and her husband Rob Onda live in The Plains. Annie spends her time riding, playing with her four brown dogs, and spending time with friends from Hill.
Mrs. Annie Bishop ’94
Board of Trustees
Mr. Matthew Blunt
Matt and his wife Melanie are the parents of Branch ‘20 and Brooks ‘24. Matt is the president of the American Automotive Policy Council, a trade association representing the common trade policy interests of FCA US, Ford Motor Company and General Motors Company. In 2004, Matt was elected the 54th Governor of Missouri. Prior to his election as governor, he served in the Missouri House of Representatives and as Missouri’s elected Secretary of State. He also served 14 years in the Navy and Naval Reserve, which included assignments on the USS JACK WILLIAMS (FFG-24), and the USS PETERSON (DD-969). As a Reservist, he was mobilized after the September 11, 2001 attacks.
Matt is a Director for Copart, the USAA Life Insurance Company of New York and Dent Wizard International and is a member of the board of business advisors for Gridiron Capital. He was also appointed by the President of the College of William and Mary to the James Monroe Commission which assists with the management of Ash Lawn-Highland, the home of James Monroe.
Matt earned his bachelor’s degree in History from the U.S. Naval Academy.
Mr. Matthew Blunt
Board of Trustees
Mr. James G. Davis
As President and CEO of DAVIS Construction since 1988, Jim oversees operations strategy, key project development, and client relationships. For over 40 years, Jim has helped transform a small family business into a nationally ranked construction leader. He is recognized by clients and employees alike for his emphasis on effective teamwork, commitment to quality and excellence in service, and ensuring the firm-wide management practice of putting the client first.
Jim is proud of the company’s reputation for honesty and integrity; a reputation which is supported by the demonstrated belief that corporate responsibility extends well beyond the bottom line. DAVIS has a genuine passion for giving back to the community, and has established long and meaningful relationships with many nonprofit organizations, education providers, small and minority businesses, and community groups. Jim continues to lead the charge at DAVIS, engaging employees at every level to contribute to the company’s community outreach efforts.
As a fourth generation construction industry leader, Jim reflects the principles of hard work and innovation in everything he does. His well-honed instincts are invaluable, and his experience and perspective are essential as the company moves forward. His pride in continuing the good work his father began is abundantly clear and inspirational to all who work at DAVIS. Jim is active within many professional organizations and serves on several boards including the National Building Museum, Boys and Girls Clubs of Greater Washington, Samaritan Inns and the DC Students Construction Trades Foundation.
Jim is married to Shannon Davis, a former Hill School Board Member and Auction Chair. Together, they have three children: Meghan, Class of 1998 Kara, Class of 2000, and Charlotte, Class of 2005.
Mr. James G. Davis
Board of Trustees
Mr. Philip Dudley ’86
Philip was raised in Upperville, VA and is the founder and Managing Partner of Dudley Capital Management, LLC based in Middleburg, VA. Previously, he held positions with Morgan Stanley & Co and Deutsche Bank Alex Brown. He is a graduate of The Hill School (’86) in Middleburg, VA, Episcopal High School (’91) in Alexandria, VA, Texas Christian University (’95) in Fort Worth, TX and Louisiana State University (’99) in Baton Rouge, LA. Three generations of Philip’s family have attended Hill. His current role as a board member and President of Hill’s Alumni Association follows board positions by his father Tim (’56), sister Anne (’83) and wife Stormy (‘81). Additionally, he serves on the investment committee for the PATH Foundation and the board of the Northern Piedmont Community Foundation and is NPCF’s investment committee Chair. Philip resides in Upperville, VA with his wife Stormy and their children.
Mr. Philip Dudley ’86
Board of Trustees
Mr. Shelton Gregory
Shelton Gregory has been part of the Hill School community since 2015 when he and his wife Polina made the decision to send their sons Micah (‘24) and Elijah (‘26) to Hill. Having attended private schools himself, Shelton continues to recognize in Hill the fundamental values that shaped the foundation of his education and equipped him for success in life. For the last 20+ years, Shelton has operated on the cutting edge of the Data Center industry. He’s led small specialized teams and massive global organizations motivating groups and individuals to tap into passion and evolve beyond assumed constraints to find innovative solutions to the most complex challenges. Shelton believes “if you can not find the solution it means you haven’t invented it yet”. This thinking has earned Shelton engineering and software patents while inspiring and enabling dozens more across the industry. A concert percussionist in his youth, Shelton savors the exploration of music in every form while indulging in reading, cooking, photography, and travel. Born in Queens, New York – Shelton has fully embraced rural living and has found new enjoyment in fishing, outdoor motor sports, and sporting clays. Shelton is excited by the opportunity to serve on the board and looking forward to deepening his relationship with the Hill School community.
Mr. Shelton Gregory
Board of Trustees
Mrs. Sheila Harrell
Sheila, Hill School class of ’86, was born and raised in The Plains, Va. After graduating from Oldfields School (’90) and Denison University (’94) she worked as a cake baker, mortgage lender, and as a Major Gifts Officer for The University of North Carolina’s Kenan-Flagler Business School. She returned home in 2014 and feels fortunate to be able to share Hill School traditions and the special community of family and friends with her husband Martin and their children Molly (’22) and Will (’24). She currently serves as the Vice President of Buchanan Hall and as a board member of The Plains Community League.
She is honored to serve on the Hill School Board. You may remember her work as Happy Johnny Jack from Saint George and the Dragon, The Angel Seagull from her 3rd grade’s Jonathan Livingston Seagull, or for her 7th grade rendition of Emily in Hunt Lyman’s first ever production of Our Town. She, however, is most proud that her 13+ girls relay team, still holds the quadra-school record.
Mrs. Sheila Harrell
Board of Trustees
Ms. Barbara Scott
Barbara Scott moved to Middleburg in 1984 to take a position at the Hill School as the first grade teacher. Her two daughters Joella (’86) and Laura (’87) attended Hill. Ms. Scott is a graduate of Southern Methodist University with a degree in Biology and English. She currently resides near Middleburg, Virginia. She is a current trustee of the Bank of Charles Town based in Charles Town WV.
Ms. Scott was CEO of Summit Point Raceway Associates Inc. (SPRA) and BSR Inc. These are the operating entities for the 785 acre Summit Point Motorsports Park located in Summit Point West Virginia. SPRA hosts motorsport events to include amateur road racing for sports cars, motorcycles, and karts. BSR Inc. provides specialty and anti-terrorist driver training programs for government agencies and the U.S. military. The facility has four European style road racing circuits and a 300 acre industrial park that houses a U.S. State Department training facility.
Ms. Scott began her employment at Summit Point in 1987 and has extensive experience in all facets of the business, by managing and operating a multifaceted and highly successful company with nearly 200 employees. The company sold and now Ms. Scott is enjoying travel and community work.
Ms. Barbara Scott
Board of Trustees
Mr. Maximilian A. Tufts, Jr.
Max and his wife Maria (PTC President 1994 -1996 and a Board Member 1996-1997) have been part of the Hill School community since the early nineties (parents of Max ‘94 and Jonathan ‘96) and are now proud grandparents of Camden ‘24, Caroline ‘24, Charlotte ’24, and Mills ‘29.
Max is a lifelong resident of Fauquier County and has been farming his family’s farm. He has been and is involved in civic and government organizations. He is a past president of Fauquier Mental Health Association and is currently President of Foothills Housing Corporation, as well as Vice Chairman of the Fauquier Board of Zoning Appeals.
Max enjoys sailing, photography, and horseback riding with his grandchildren. He is excited to join the Hill School Board and is looking forward to reconnecting with old friends and making new ones.
Mr. Maximilian A. Tufts, Jr.
Board of Trustees
Mr. David Walker
David Walker has been part of the Hill School community since 2014 when he and his wife Anne (Dudley) Walker (’83) made the decision to send their daughter, Elizabeth (24’) to Hill. Anne, her brother, Philip Dudley (’86), and her father, Tim Dudley (’56) all attended Hill.
David has worked in the software industry for about 34 years. He has spent the last 18 years with Microsoft Corporation, currently as a Senior Director in the Federal Subsidiary, responsible for Microsoft 365 (Windows, Office 365 and Devices) sales and product strategy. He has spent a significant amount of time in his prior roles both inside and outside the US with posting in Australia, Asia-Pacific, the UK and Latin America. David grew up in Northern Virginia and lived overseas several times. He enjoys cooking, gardening, collecting rare and antique books and woodworking. David currently serves on the board of the Community Music School of the Piedmont as Treasurer.
He is excited by the opportunity to serve on the Hill School Board of Trustees and growing his relationship with the Hill Community.
Mr. David Walker
Board of Trustees
Mrs. Anne duPont Westbrook ’75
Anne graduated from Hill School in 1975. She attended Foxcroft School and Case Western Reserve University. She is currently a Senior Vice President with Heitman, LLC, a Chicago-based real estate investment management firm. She is responsible for all marketing and capital raising assignments in the Southeastern United States. Heitman currently manages over $37 billion of commercial real estate investment on behalf of public and corporate pensions, endowments and foundations. Prior to joining Heitman, Anne was a Managing Director and Co-Principal with Berkadia Capital Markets, LLC and responsible for all broker dealer related business including private placements and the sale of 144(a) securities. She has been a commercial real estate professional since 1985 and held investment and capital markets positions with Credit Suisse, Soros Fund Management and was the founder and Principal of Beekman Capital Partners, a real estate private placement firm. Anne has formerly served on the Board of St. Michaels Country Day School in Newport, RI and also chaired the schools finance committee. Her daughter, Bettina Corbin, graduated from Hill in 2015.
Mrs. Anne duPont Westbrook ’75
Board of Trustees
Mr. Jesse White
Jesse and his wife Kim relocated to Northern Virginia 8 years ago with their daughters Isabella (Hill ’20) and Camilla (Hill ’26), from the Hudson Valley in NY, where Jesse grew up, and by way of Boston, where Isabella was born. Jesse is passionate about Hill’s philosophy, community, and the experience of his two daughters. Jesse and family now live in Paeonian Springs, VA. Jesse began his career as a technology entrepreneur, has built 4 technology service businesses in the last 21 years, and has served on the board of multiple local not-
for-profit organizations and IT industry boards. He currently serves as President and Partner at Intact Technology, a high growth National provider of IT Management services to the Fortune 1000 and US Federal Government. Over the last 12 years of his tenure he has increased Intact’s’ revenue over 15X with the culture of the business being the primary focus. He believes that the best in class experience of their customer begins and ends with the experience and engagement of each employee. In his spare time, he loves spending time outdoors with his family, alone on his bike in the hills of Northern Virginia, or learning something new.
Mr. Jesse White