Jessie Waites

When asked what it means to be an Oakie, English teacher and 10th grade Class Dean Mrs. Jessie Waites said that the relationships within the school are founded on goodwill and trust.

“What I find really beautiful is that everyone here, from the students to the faculty and the faculty to the students, everyone really does want the other to be happy, and they are willing to walk with you to get you there,” she says. 

A Michigan-native, Mrs. Waites was born and raised in Michigan and attended Hillsdale College for her undergraduate degree in Psychology, also minoring in English. 

After graduating, Mrs. Waites taught at Northwest Ohio Classical Academy in Toledo, Ohio, where she taught fourth grade and was a founding member of the school’s special-education program team, aiding students with social and learning difficulties. It was here where her love for teaching at a school with a rich, liberal arts curriculum deepened, especially with its emphasis on the formation of the whole person and the inclusion of reading the Great Books. 

When she moved to Virginia after getting married, Mrs. Waites said she “stumbled” upon Oakcrest School. 

“It worked out so perfectly,” she says. “I was looking for Catholic schools in the area and I had no idea that Oakcrest was so amazing.” 

She recalls a certain moment when she attended Mass at Oakcrest during her interview, and then found herself in the exact same seat at Mass, six months later. “I had no idea the role that Oakcrest would play in my life,” she said. 

Initially drawn to Oakcrest because of the school’s liberal arts curriculum and mission, Mrs. Waites has had a love for the “holistic side of the liberal arts,” she says. “In the classroom, there is an education of the mind as well as movement of the heart.”

Mrs. Waites also said she is constantly grateful for the support that the faculty provide one another. “There isn’t a culture of complaining,” she explains. “Our teachers are joyful and they love what they do. That was evident right when I stepped into the school.” 

“I feel very blessed that I get to work in a place that I sincerely like going to. When people ask me about my job, I can sincerely say, ‘I love it’.”

For the past two years, Mrs. Waites has coached Varsity Cross Country and Middle School Track and Field. 

“As a coach, I’m able to see the girls from a different perspective, through character formation on the cross country course,” she says. “It’s fun to get to know the girls outside of the classroom. I get to see their personalities in a different light and see their leadership skills come out. It’s sometimes different who takes the lead in the classroom and who takes the lead outside the classroom.” 

Also serving as the 10th grade dean, Mrs. Waites said she also has the opportunity to get to know the students’ personalities outside of their academic abilities.

For the past two years, Mrs. Waites has spoken to the graduating senior class during senior Lead Days, a two-day conference for seniors at Oakcrest to glean some wisdom about the practicals of a college experience from their teachers and other mentors. The topic that she has shared with them is “Building Friendships in College,” where she discusses how to make the transition into college and setting boundaries within a new stage of life. 

“I hope that their main takeaway is that people are drawn to authenticity. They have been lucky to be raised and educated in a place that was safe for them to make mistakes and really find who they are (here at Oakcrest),” she said. “My hope is that they can go out and begin this next stage of life with the confidence that often takes others a long time to build in college. Our students know what it takes to live a good life, and they don’t have to face an intense period of self-doubt and struggle because they have a firm foundation built at Oakcrest.”