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 five times per year. The Board standing committees include: Alumni Association, Development, Education and School Life, Executive, Finance and Endowment, and Marketing.
The Board of Trustees for the 2023-2024 School Year is below. Here a list of Past Board Presidents who have served Hill School.
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.
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, then after nearly 20 years in consulting founded Operating Partners Group, LLC – an M&A and post-merger integration advisory firm. 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 Andrew, Hill ’19). When he’s not working on the next interesting client challenge, he’s most likely enjoying time with family and friends on the golf course, or wherever they are. Erich enjoys golf, skiing, and being outdoors, and is gratified and humbled by the enduring connection to the Hill School community
Board of Trustees
Mr. Matthew Blunt
Treasurer
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. Matt, Melanie, and their boys enjoy being a part of the Hill community.
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.
Board of Trustees
Mrs. Annie Bishop ’94
Annie was born and raised in Middleburg. Annie was lucky to be a part of the 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 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.
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.
Board of Trustees
Mrs. Matilda Reuter Engle
Matilda Reuter Engle, a seventh-generation Middleburg native, is the dedicated proprietor behind Middleburg Hospitality, which includes the iconic properties of The Red Fox Inn & Tavern and Glenstone Gardens. With nearly three decades of hospitality experience, she has seamlessly blended the historical charm of Middleburg with modern luxury, ensuring every guest experience reflects the unique character of the Virginia countryside. As the creative visionary, Matilda continues to uphold the brand’s mission of promoting Inspired Entertaining in the Virginia Piedmont.
Matilda’s hospitality journey began at The Red Fox Inn & Tavern, a national landmark dating back to 1728, where she worked hands-on washing dishes and waiting tables in the family business. Today, as the third-generation proprietor, she is committed to preserving The Red Fox’s 300-year legacy as the iconic cornerstone of Middleburg, renowned for its warm country house atmosphere, authentic Virginia hospitality, and seasonal Piedmont Cuisine. Her leadership and vision extend to Glenstone Gardens, her family’s circa 1750 private estate that serves as the backdrop to a handful of ultra-luxury weddings and events each year.
Matilda attended The Hill School, Episcopal High School, and James Madison University, where she met her husband, Jonathan Engle. After beginning her career at the Biltmore Estate in Asheville, North Carolina, she returned to Middleburg to carry on her family’s legacy in hospitality.
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.
Board of Trustees
Mrs. Sheila Harrell ’86
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.
Board of Trustees
Mr. Adam Jackson ’97
Adam is Partner at Bosch Ventures, a $850M Venture Fund backed by the Bosch Corporation focused on investments in the Mobility, Clean Tech, AI, and Healthcare Diagnostics space. Previous to Bosch Ventures Adam ran the Venture arm of the Bose Corporation for six years. Prior to focusing on Corporate Venture Adam spent 10 years as a Venture Capitalist in the telecommunications industry with Argo Global Capital deploying over $75M in equity in over 20 early- and mid-stage investments through 60+ financings, 10 M&A events, 1 IPO and participation on 10 boards as either a director or observer. Adam is a graduate of Cornell University and currently lives in Boston with his wife Ashley and two young daughters.
Board of Trustees
Mrs. Amy Miller
Amy was born and raised in Maryland. She earned her Bachelor’s in History and Economics from Hollins University. As a scholar athlete she also rode on the equestrian team and played lacrosse. While in graduate school Amy pursued her dream of riding horses professionally. Amy now works for the family’s Millbrook Companies, which provides soils to construction and environmental restoration companies. She is a committed parent-volunteer at The Hill School where she served as the PTC President (2021-2024). Amy is married to Mark (Hill ’91), and is the mother of three active children: Lizzie (Hill ’24), Sara (Hill ’26), and Marty (Hill ’29). She continues to ride and enjoys supporting her kids in their own extracurricular endeavors. Amy is grateful her family is part of the Hill community, and she looks forward to continuing to serve The Hill School as a member of the Board.
Board of Trustees
Ms. Reid O’Connor ’09
Reid was born and raised in Paeonian Springs, Virginia, and was lucky enough to be part of the Hill School Class of 2009. After Hill, Reid attended the Maderia School and then the University of St Andrews in Scotland where she studied Art History and Italian. Following college, Reid joined the team at the National Sporting Library & Museum in Middleburg where she has spent the last seven years, now in the role of Director of Development.
Reid is the current President of the Hill School Alumni Association and has been proud to serve on the Alumni Association board for the past five years. She also previously served as the Secretary of the Loudoun County Equine Alliance.
Reid currently lives in Upperville, and spends her free time riding, playing tennis and polo, and being outdoors with her spaniel, Tweed.
Board of Trustees
Mrs. Jade Pulliam
Jade Pulliam was born and raised in Toronto. After graduating from the University of Toronto in 2006 she founded an event company and for almost two decades created luxury events around the world. Jade serves as the co-chair of Better Together at Hill, a parent club to develop a culture of Inclusivity and Multiculturalism, where she produces a series of events that focus on bringing the Hill community together. Jade is married to her husband James (Class of ‘97) and they along with their two children Jet ’29 and James IV ’31 live in Middleburg.
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.
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.
Board of Trustees
Mrs. Cristin Wipfler ’94
Cristin (Hill ‘94) and her husband, Mike (Hill School faculty 2001 – 2019) are the parents of Liam (Hill ‘26) and Olivia (Hill ‘31). After completing her undergraduate degree at The University of Notre Dame, her Master’s Degree in Public Health from George Washington University, and receiving her credentials as a Registered Dietitian, Cristin opened her private nutrition practice in Middelburg and continues to enjoy bringing health and wellness to our local community and beyond. In addition to her work in nutrition, she is passionate about creating conversation around body image and body dysmorphia in the hopes of giving girls the confidence to live their life based on purpose, not appearance. Outside of her work, Cristin loves spending time with her family, taking walks with friends or a good podcast, cheering for her favorite college team, and reading.
