Collegiate School
At Collegiate School, Penny B. Evins took the reins as head of school in July. She replaces Steve Hickman in leading the 1,679-student college preparatory institution. The Henrico County school consists of a lower, middle and upper school; a separate athletics complex; and an aquatics center.
Evins comes from the top position at St. Paul’s School for Girls in Brooklandville, Maryland, which followed a succession of roles with increased responsibilities at well-known private schools. Evins, a University of Virginia graduate, started her professional life as a school counselor.
“At my core, I am a counselor,” says Evins, who was born in New Orleans, where she attended, and years later worked at, the Isidore Newman School. “That’s what I bring back: listening and the power of community and the power of care.”
With an eye to the school’s reputation and its values of citizenship and achievement, Evins takes a marathoner’s approach to education, slowly building on successes. Collegiate’s more than 100 years of history was a draw for Evins, who reflects that beginnings and changes are constant in education.
“The past performance of students is not fixed. Yes, it informs us of habits,” she says of those who study at Collegiate from junior kindergarten through 12th grade, spending as many as 14 years on campus. “It does help us, as educators, to understand habits, and it helps us to help students reach their potential. We are mindful of the past in a way so that it serves [students], but not that it creates a stereotype of them for school.”
There is, she says, always room for individual and collective change and improvement. She points out the value of learning beyond textbooks, digital citizenship and putting electronics down to have meaningful conversations.

Robert “Bob” E. Gregg III (Photo courtesy St Michael’s)
St. Michael’s Episcopal School
At St. Michael’s Episcopal School, Robert “Bob” E. Gregg III is the new academic leader of the parochial school for kindergarten through eighth grade students. The Massachusetts native is a longtime private school educator and administrator who comes to St. Michael’s from his position as head of school at Green Hedges, a preschool through grade 8 independent school in the town of Vienna.
“We are thrilled to have attracted a leader with Bob’s leadership and collaborative abilities, commitment, integrity and passion for educating the whole person,” says St. Michael’s Board Chair Kim Daniels in a written statement. “His dedication to students and his expertise with both school leadership and student learning are qualities the board felt were essential in our next head of school.”
Gregg was drawn to St. Michael’s because of the success of the One Together Capital campaign, the strong academics and the stability of the position. He also shares the school’s focus on making sure students entering high school are prepared for the experience.
“St. Michael’s is very much involved in helping eighth grade students and their families navigate their high school options, and my experience as a school leader is in that school match process and helping families find that just right school. In Richmond, there are a plethora of choices,” he says.
St. Michael’s One Together campaign saw through the construction of a new multipurpose Hubbard Hall and Lower School on its Hobby Hill Road campus during the last academic year. The school is also building a new assembly hall. Gregg’s skill set matches with St. Michael’s expansion, as he brings experience in team building and capital campaigns with building construction.

Tom Bendel (Photo courtesy Sabot at Stony Point)
Sabot at Stony Point
The new director of Sabot at Stony Point is Tom Bendel, who replaces longtime Head of School Irene Carney upon her retirement. The secular, progressive institution with a preschool, lower school and middle school is marked by a Reggio Emilia-inspired, social constructivist, inquiry-based curriculum for approximately 200 students.
While Bendel’s most recent position leading the North Jakarta International School in Indonesia was far-flung, the experienced private school educator and administrator has a longtime Richmond connection as a Virginia Commonwealth University graduate with adult children in the area.
After many years as an officer and instructor at the U.S. Naval Academy in the political science department, he shifted to teaching to a younger demographic at independent private schools where he also worked in leadership positions.
“Here, we teach students with content, but we don’t teach them the content,” Bendel says of Sabot’s approach. “We teach so children know how to acquire new knowledge.”
He says his political science background translates to conveying concepts of good citizenship and forming a strong community. He previously served as the head of the Upper School at the Rabun Gap-Nacoochee School in Georgia and dean of student affairs at the American School in Switzerland.
The school aims to grow during Bendel’s tenure with a $2 million capital campaign underway that includes plans to construct a 16,000-square-foot building with 16 classrooms, and a science lab.

A rendering of St. Catherine's new arts center (Image courtesy St. Catherine’s)
St. Catherine’s School
In Richmond’s West End, St. Catherine’s School is engaged in a search for a new head of school as Terrie Hale Scheckelhoff, who has led the school since 2012, retires next June. Semifinalist candidates will be interviewed by the search committee this fall.
Dr. Anne McElroy, an alumna from the class of 1978 who is co-chair of the search committee and former chair of the board of governors, says via email, “We are looking for our new head of school to be a dynamic and visionary leader, who will be fully engaged in our school community and the Richmond area. The next head of school will be expected to continue our legacy of excellence in girls’ education.”
St. Catherine’s students will benefit from the recent completion of its first phase of its of campus renovation, resulting in an on-campus artificial turf field for games and practices, as well as physical education classes, recess and outdoor education. A new playground at the school was designed with girls in mind, with equipment and activities to cultivate upper body and core muscles as well as problem-solving abilities. On the school’s horizon is a new Arts and Innovation Center (above) that will feature a 550-seat theater with community spaces for the arts and gatherings. The school recently donated its former theater seats to George Washington Carver Elementary, which installed them in its aging auditorium.
“With our ongoing campus projects and the head of school search, this is an exciting time at St. Catherine’s,” McElroy wrote.