Caleb was elected to the Williamsburg City Council in May 2020. In his Council appointments, he serves on the boards for Olde Towne Medical Center, Virginia First Cities, and Virginians for High Speed Rail. Also in May 2020, Caleb graduated from the College of William & Mary with a B.A. in Public Policy. As a student, he directed fundraising campaigns for the House of Mercy, a regional complete care center for the homeless. He also served a partial term on the Planning Commission and interned in the City’s Economic Development Office.