Our School
Our Leadership
Head of School

Incoming Head of School

Collegiate School's Board of Trustees unanimously voted on May 28, 2018, to name Penny B. Evins the next Head of School, beginning in July 2019, upon the retirement of current Head of School Stephen D. Hickman. Ms. Evins will come to Collegiate with extensive experience in the independent school arena. She and her family are honored to be joining the Collegiate community.
“Throughout my career, I have admired Collegiate as a national model of independent school education. My esteem for Collegiate as a compassionate, close-knit community grows with each and every person I meet. I am honored that members of the Board of Trustees would place their faith, support and trust in me as Collegiate’s next Head of School. I look forward to working with everyone in the Collegiate community to fulfill the mission sparked by Helen Baker and carried forward by past and current generations.” – Penny B. Evins, Incoming Head of School, July 2019


Head of School
St. Paul’s School for Girls
Brooklandville, Maryland
Leads an early childhood through Pre-Kindergarten program and
the 5th-12th Grade girls’ school;
has launched numerous innovative programs, incorporated inquiry-
based electives into the curriculum
and increased enrollment and

Lower School Head
Isidore Newman School
New Orleans, Louisiana
Led an 80-member faculty and 450
students from Pre-Kindergarten through 5th Grade and revamped
the curriculum and strategic, growth-oriented evaluation of faculty.

Strategic Planning Consultant/Admission Associate
The Lovett School
Atlanta, Georgia
Conducted peer research on
benchmark schools and organizations around the nation regarding student life programs; led focus groups for students and faculty; and produced an action plan for school administrators and board members.

The Lovett School
Atlanta, Georgia
Oversaw the emotional, social and academic well-being of approximately 450 students in 6th-8th Grades; taught ethics and coached soccer.

Middle School Head
The Webb School of Knoxville
Knoxville, Tennessee
Led the division, 5th-8th Grades, of
approximately 350 students and 50
faculty members; taught 6th Grade English; and continued serving as
Upper School Counselor.

Upper School Counselor/Administrator
The Webb School of Knoxville
Knoxville, Tennessee
Served as the school’s first Upper
School Counselor; designed and
implemented programming; taught ethics and coached soccer.


University of Virginia
M.Ed., Counselor Education - 1996
Advanced Studies, Chi Sigma Iota
Honor Society

University of Virginia
B.A., English - 1994
Dean’s List

Dear Collegiate School Community,

On behalf of the Collegiate School Board of Trustees and the School Search Committee, we are delighted to announce the appointment of Penny B. Evins as our next Head of School, effective July 1, 2019.

Penny’s appointment is the culmination of a nine-month national search that drew interest from a wide and diverse range of accomplished educators.

Early in the process, we established an Advisory Committee comprised of Collegiate faculty, students and alumni. We also engaged an independent school search firm, Carney Sandoe & Associates (CS&A), whose representatives visited campus and interviewed faculty, staff, students, parents, alumni and administrators. CS&A also surveyed the Collegiate community. Through this research, we learned that Collegiate stakeholders are united around the distinct leadership values that we want in our Head of School – integrity, vision, compassion, inclusivity, a strong sense of community, and a passion for education and children.

Penny possesses all of these values and more. Throughout her career, she has demonstrated the professional agility necessary to lead across all areas of independent school life. She has a passion for setting every student on a pathway to success and a strong appreciation of school culture and community.
We are thrilled to have found such an exceptional leader who is so aligned with Collegiate’s core values and aspirations. We fully expect Penny will move our strategic priorities forward in a way that unites everyone around Collegiate’s timeless mission.  

Penny was born in New Orleans where she attended Isidore Newman School. She is a graduate of Choate Rosemary Hall in Connecticut. She received a B.A. in English and M.Ed. in counselor education from the University of Virginia. Penny will come to Collegiate after a successful six-year tenure as Head of St. Paul’s School for Girls (SPSG) in Baltimore, Maryland. While at SPSG, Penny led the school’s healthy growth in enrollment, contrary to both local and national trends in independent schools. She also introduced innovative programs, including off-campus real-world experiences for students and new electives to enhance the overall curriculum.

Prior to her service to SPSG, Penny held a wide variety of positions, including counseling, admissions, strategic planning and division-level headships at some of the leading independent day schools in the Southeast.

Penny and her husband Sam, also a longtime independent school educator and coach, have two teenage children, Sam and June Friend, who will attend Collegiate. We are looking forward to welcoming the Evins family to Richmond and our Collegiate community.

We are thankful for the hard work and wisdom of the Search Committee and Search Advisory Committee members, and the valuable input we received from nearly 1,000 members of our extended Collegiate family. Moreover, we are deeply grateful that Penny and her family have chosen to join us as Collegiate moves forward.

Best wishes,


Frank F. Mountcastle III
Chair, Board of Trustees

John W. Martin
Vice-Chair, Board of Trustees
Co-Chair, Search Committee

Michelle Wiltshire
Board of Trustees
Co-Chair, Search Committee

“The Board of Trustees has made an inspired choice in naming Penny B. Evins as Collegiate’s next Head of School. Penny brings extensive independent school leadership experience, a demonstrated capacity for community-building and a proven commitment to Collegiate’s core values and strategic priorities. She is the right person at the right time for the right reasons.”

– Stephen D. Hickman, Head of School

Learn More About Penny B. Evins

List of 7 frequently asked questions.

  • How would people describe you as a person?

    Thoughtful, personable, morally grounded, warm, engaged, committed, determined, caring, strong, hopeful, clear in my convictions, intentionally focused on wellness.
  • Give us an overview of your career experiences.

    All but one of my jobs involved working with children, families and in education. Truth be told, when in graduate school I was a waitress. I was very bad at it, and only made good tips when children were at my tables. That was a sign to stick with school communities! I have served as an administrator, division head and/or counselor in all three divisions of independent schools, as Head of School at a girls’ school on a coordinated campus, and as a consultant for strategic planning and in the admission realms. I have had the privilege of wearing all hats — from carpool to being the last one on campus — as I served as a Head of School for St. Paul’s School for Girls. I also took two years to be at home with my children when they were younger, while my husband served as an Upper School Head. That job taught me a lot about what matters and grew my appreciation for those who have careers in their homes, as did my own mother.
  • What are your thoughts about education and what trends are you following?

    We must consider the rapidity of communication and the increased access to information that our students have as digital citizens in 2019. However, we are still human beings and thrive in communities where we feel known, valued and understood. As such, the role of teachers is not to be a gatekeeper of information but instead a facilitator of learning and optimal communication. Building trust and fostering environments where healthy risks are modeled and praised are hallmarks of nimble and noteworthy educational settings. I believe in a fluid and normalized feedback loop. A noisy hum of learning is, in my opinion, sacred and noteworthy. Educators are carpenters of the heart and mind; they focus on content and character, and without one, the other does not flourish. Vibrant learning communities foster conversation, interdisciplinary studies, failing forward, community partnerships, real-world exploration and the mastery of skills through a range of discoveries and studies. There is no one way to teach, just as there is no one Collegiate Cougar. In sum, I believe relationships and exploration in communities where there is a continuity of care, support and challenge are timeless and precious hallmarks of thriving and future-focused learning communities. Mission-driven education strives to graduate good citizens who will impact the greater world in positive ways and enjoy doing so.
  • What do you believe are the key attributes of great independent schools?

    Each employee is seen as, and (sees themself as) an educator. Great schools know their mission is the guiding force, glue and filter for decisions small and large. It is not about the “newest and shiniest idea,” but about that which resonates, is mission appropriate and helps the school achieve its vision. It is a true community where all feel welcomed, heard, valued and understood. Such schools do not rest on their laurels, but instead are constantly seeking ways to improve and grow, just as we ask our students and faculty to do. The constituents feel involved with the future and share great moments and passion for the past. There is spirit and joy in daily interactions. The community members are natural and authentic ambassadors of the school, and there is authentic support to become one’s best self. Success is celebrated, sadness survived together and named emotions are teachable moments.
  • How would people describe you as a Head of School?

    Warm, committed to character education, communicative, enthusiastic, engaged, patient, focused, community builder, optimistic, responsive, calm in a crisis.
  • What do you like the most about being a Head of School?

    Every single part of it, especially the children.
  • What can you share about your family?

    I met my husband doing cafeteria duty at The Lovett School in Atlanta. We are school people. We are a bit of an open book and currently live on campus. We call ourselves Team Evins. We don’t keep secrets and we love each other dearly. My husband Sam V is my No. 1 partner and best friend. He is king of breakfast at our house, and bacon is frequently on the griddle. He loves teaching, coaching, history and nature. Outdoor fitness is his favorite hobby. We share that. Our son, Sam VI, a rising 10th Grader, has listened to sports radio since his days as a toddler who woke up before 5 a.m., and as such, knows a lot about sports history and current news. He has gone to sleepaway camp since 2nd Grade and adores his “boy heaven,” where I don’t ask him to eat fruits or vegetables, brush teeth or do other such mundane things. He has great friendships and strong relationships with his teachers, coaches and all members of our community. June Friend, our daughter, is named after my maternal grandmother. She loves the arts, enjoys nature and hiking with others, cooking, being with her friends, is readying for her seventh year of sleepaway camp and is a rising 9th Grader. Both were in the Lower School when I was Lower School Head at Newman, and my husband and sisters worked there, too. We don’t know what it is like not to be in the same community. We are pretty regular and try to have family dinner often. The star of our family is our dog, Ansley, who comes to school each day and knows everything and shares nothing but love!

We extend our deep appreciation to the following individuals for the time, wisdom and care they dedicated to our search process.


John W. Martin '78, Board Vice Chair, Past Parent '10, '11
Michelle Wiltshire, Trustee, Past Parent '07, '10
Charlie Blair, Middle School Head, Past Parent '01, '04, '06, '10
David Gallagher, Trustee, Parent '18, '24
Frank Mountcastle '83, Board Chair, Parent '14, '17, '21
John O’Neill, Jr., Immediate Past Board Chair, Parent '13, '16, '17, '21
Carter Reid, Trustee, Parent '16, '18
Danielle Scott, Trustee, Parent '25, '25
Mark Stepanian '89, Trustee, Parent '16, '18, '21, '23
LaNessa West, Lower School Co-Chair of Academic Services, Parent '19, '21


Mike Boyd, Director - Performing Arts, Parent '25
Mason Chapman '84, Former Alumni Association President, Parent '22
Caroline Hall '18, Student Cooperative Association (SCA) Co-Chair
Terrell Harrigan '77, Former Trustee, Past Parent '09, '11, '14
Beth Hutchins '88, Alumni Association President, Parent '19, '21
Meg Johnson, Parents’ Association President, Parent '17, '19
Brian Leipheimer, Director - College Counseling, Parent '23, '24
Shep Lewis '96, Senior Director - Annual and Leadership Giving, Parent '29
Spencer Lyons '18, Student Cooperative Association (SCA) Co-Chair
Kimara Parker, Parents’ Association Middle School Coordinator, Parent '22, '25
Scott Ruth '91, Alumni Association Board Member, Parent '19, '22, '25, '27
Clare Sisisky, Director - Institute for Responsible Citizenship, Parent '29
Alex Smith '65, Vice President - Development (Retired), Past Parent '90, '94, '00, Grandparent '25, '28
Jasmine Turner '11, Alumni Association Board Member
Stew Williamson, Upper School Faculty

Board Members

John W. Martin ’78 Chairman of the Board
Mason T. Chapman ’84 Vice
Chairman of the Board
Frank F. Mountcastle III ’83
Immediate Past Chairman of the Board
Penny B. Evins
President/Head of School
Phyllis Palmiero
Susan C. Wiley
Ellen T. Bonbright ’86 P ’24 ’26
Callie Lacy Brackett ’95 P ’22 ’24
Mason T. Chapman ’84 P ’22
Jeffrey W. Congdon ’78 P ’02 ’05
Mayme Beth F. Donohue ’03
Penny B. Evins P ’22 ’23
David A. Gallagher P ’18 ’24
Eucharia N. Jackson P ’17 ’19
Michael S. Laming P ’17 ’19
H. Pettus LeCompte ’71 P ’99 ’01**
Peter E. Mahoney, Sr. P ’15 ’19 ’26 ’26
Neelan A. Markel ’96 P ’27 ’30
John W. Martin ’78 P ’10 ’11
Malcolm S. McDonald P ’87 ’88*
Morenike K. Miles P ’24 ’25
Frank F. Mountcastle III ’83 P ’14 ’17 ’21
William S. Peebles IV
Carter M. Reid P ’16 ’18
Lisa E. Roday P ’09 ’10
Kenneth P. Ruscio P ’08
Jennifer J. Ruth ’90 P ’19 ’22 ’25 ’27***
Danielle D. Scott P ’25 ’25
L. Mark Stepanian ’89 P ’16 ’18 ’21 ’23
Wallace Stettinius P ’77 ’79 ’84*
W. Hildebrandt Surgner, Jr. P ’11 ’14 ’17 ’19
Robert S. Ukrop P ’88 ’89 ’92 ’95*
R. Gregory Williams ’69 P ’01 ’04*
*      Life Trustee
**    Parents’ Association President
***  Alumni Association President