Shannon Grimsley: ‘Cheerleader-in-chief’ for Rappahannock County Public Schools

The ‘super’ in school superintendent takes on new meaning

Grant writer extraordinaire, school bus driver, student advocate — Shannon Grimsley is redefining the role of Superintendent of Rappahannock County Public Schools.

Since becoming the top administrator of the school district seven years ago, Grimsley, 40, has become a champion of student success in Rappahannock as well as at the state level. She represents all of the schools in Northern Virginia as a regional chair for the Virginia Association of School Superintendents, and works to give rural districts a voice in statewide issues.

A hallmark of Grimsley’s tenure has been her grant-writing ability and impact on grant funding in the district. Since 2017, over $3.6 million in grant revenue has made its way to Rappahannock County Public Schools. Largely through her efforts, students have access to career-centered courses, healthy lifestyle initiatives and other unique programs that would not be possible with general funding.

Grimsley added a new job to her resume last year – bus driver. The mother of three stepped up and completed dozens of hours of driver training and certification, and started picking up bus routes in response to the shortage of school bus drivers that Rappahannock, like other schools in the nation, was experiencing.

To achieve all this, Grimsley relies on her husband Rocky, a stay-at-home dad, who she says is her greatest support—him and her Christian faith. The family of five lives on a farm in Boston, Va. All three of the couple’s children are students in Rappahannock County schools–Lily in 10th grade, Rose in 7th and Seth in 4th. 

Grant success

Grimsley attributes the school’s success in receiving grants partly to the late Rappahannock philanthropist Bill Dietel, who she heard speak at a board meeting petitioning the school system to do something she had never thought of —seeking out grants to fill gaps in funding. 

Grimsley gained experience in technical writing and grant writing while completing her master’s degree, and recruited Todd Endo and the late Bev Hunter, who had both been federal grant writing evaluators, to help build her grant writing skills by editing her grant applications and coaching her on application design and scoring. 

“We do all we can to offset the very high expense of educating students–right now it’s very high–with the higher the need, the higher the cost. But also, we do want to be a school district that this community is very proud of,” Grimsley said.

Driving a bus

Since the COVID-19 pandemic, schools across the nation have experienced bus driver shortages and Grimsley saw the need for drivers in her district. She got her Commercial Driver’s License which was no easy feat–the course requires 34 hours of classroom and on-the-job training–and started driving before and after school.

“I feel like it’s all of us together, roll up your sleeves, I won’t ask you to do anything I won’t do,” Grimsley said. “There’s no better way to understand the challenge we’re having than actually to go through it.”

Jerry Goebel, an 11-year bus driver at RCPS who trained Grimsley for her Virginia Department of Transportation test, said she was not afraid to roll up her sleeves and climb underneath a bus in the shop.

“Not everyone has the right disposition to sit there and have 50 screaming kids behind you doing what they want,” Goebel said. “[Grimsly] loves the driving part–couldn’t wait to get behind [the wheel]–and she’s done really well.”

Bus number six is her go-to. While it is not the newest, shiniest bus, Grimsley’s warmth radiates when she opens the door for her students. She said it has been great to connect with children and their parents on a new level and witness first-hand how important drivers are to a student’s experience. After finding drivers to fill all open positions, Grimsley stayed on as a substitute.

Goebel said he feels that Grimsley understands the work of the transportation department and can communicate its needs better to the rest of the administrative staff.

“We’re out there, six o’clock in the morning, in the dark, in the rain, in the mud, crawling under the bus, looking at things with a flashlight. She kind of understands that…other people–they don’t come in till eight o’clock in the morning. They have no idea what we’re doing out there,” Goebel said.

“Having that connection really helps me advocate for the drivers and for what they’re going through and experience,” Grimsley said.

‘Above-and-beyond work’

Grimsley is fondly referred to by school staff as “Cheerleader-in-Chief,” and the title often appears under her name in places like her email signature. Wes Mills, chair of the Rappahannock County School Board, says it’s a title she more than lives up to. Mills said Grimsley is beloved by students and staff, and she is the best superintendent he has seen in the district in his 20 years on the School Board.

“She’s a cheerleader for the staff, and is an advocate for the children always,” Mills said. “She has consistently exceeded our expectations as far as her ability to manage the [school] system.”

Grimsley also has been a powerful advocate for the school system and others like it at the state level as the Region IV chair of the Virginia Association of School Superintendents (VASS).

Scott Brabrand, executive director of VASS, sees Grimsley as a “rising-star superintendent.”

In small districts like Rappahannock, Brabrand said, more responsibilities fall on the superintendent, and they have to learn to be a jack of all trades, whereas larger districts have fully-dedicated departments. Brabrand said Grimsley has used her experience to become a strong voice for rural school divisions.

“She’s just multi-talented, very skilled, and solution-oriented, which is what we need in public education more than ever,” Brabrand said. “Her love for Rappahannock County has her doing really above-and-beyond work for her school district.”

Grimsley is also involved in the Coalition of Small and Rural Schools of Virginia, an advocacy group created to help small districts build a strong collaborative partnership to leverage in state matters.

Finding balance

Grimsley says she believes education is her true calling. When she started her college career at the University of Massachusetts, she intended to complete a computer science program before her love of literature turned her toward an English Language and Literature Degree. In her junior year she took an English Literature secondary teaching class, and she was hooked.

“When you know something and you know your calling–it hit me like a brick wall.” Grimsley said. “Ever since then, I’ve poured everything into education.”

Originally from Massachusetts, Grimsley and her husband, Rocky, moved to the area to settle and raise their family. While in college, Shannon met Rocky by chance while she was on a blind double date with someone else. Since then, she said the couple has been “pretty smitten with each other,” and that he is her biggest cheerleader.

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When Grimsley started pursuing a career in school administration, it became clear that the long hours, hard work and further education she would need would be a challenge. The couple wanted to raise their family with a parent at home, and when a full-time opportunity at RCPS presented itself at the same time Grimsley was pregnant with their first child, her husband, who was working as a machinist, volunteered to stay home.

“I was supposed to stay home, and my husband said, ‘You’re not going to be able to stay home,’’’ Grimsley said. “He said, ‘I’ll do it’…and he’s done that ever since. We raised our three kids that way.”

Grimsley said the pressure as a woman in leadership can be weighty, with family expectations piled on top of that. She said her husband’s support has alleviated a lot of that pressure and she has been able to maintain a better work-life balance.

When Grimsley is not tending to the needs of the district, she enjoys caring for her chickens, goats, pigs and other farm animals. Responsible for their morning feeding, Grimsley said getting that time with them grounds her for the day.

Faith is also a driving factor in her life, and she leans on it in everything she does. She and her family are members of Reynolds Memorial Baptist Church in Sperryville, and she sings with the church’s praise team.

Grimsley grew up Northern Baptist, but her family stopped practicing after her parents divorced. Grimsley said she strayed from her faith for a while, but when she met her husband who had a very strong faith, the couple began practicing together, and immediately connected with their church family.

Rappahannock has become a “magical place” for Grimsley, mostly due to the people, she says. Despite the occasional joke about her Yankee roots, Grimsley said she has felt nothing but welcome by the Rappahannock community.

“I feel like Rappahannock’s adopted daughter, they just sort of welcomed me. Because of that, I just feel such an inclination to give back and support this community,” Grimsley said.

As for her future in the county, Grimsley says she sees herself here for the long haul.

“I really love this role, but I love here, and I don’t know if I would love it anywhere else,” Grimsley said. “My dream is to retire here, and I can always be a bus driver if it doesn’t work out.”

Foothills Forum is an independent, community-supported nonprofit tackling the need for in-depth research and reporting on Rappahannock County issues.

The group has an agreement with Rappahannock Media, owner of the Rappahannock News, to present this series and other award-winning reporting projects. More at foothillsforum.org.