Director of Student Transportation

Daniel Winston joined OSSE in April 2026 as the Director of Student Transportation. Danleads OSSE's Division of Student Transportation (DOT), coordinating and managing the executive team, providing organizational guidance, making critical budgeting decisions, and representing DOT within OSSE.

He previously served as Vice President of Business Development for Inspiration Mobility, a company focused on the electrification of transportation. As Vice President of Market Operations and a Regional General Manager for e-scooter and e-bike company Spin, he led multiple teams with more than 1,000 employees across more than 50 locations–from directors to hourly mechanics and operations specialists–to achieve high performance, execute safe operations, and meet compliance targets. Earlier in his career, Dan served as Director of Administration at a MetroAccess contractor. He is a former ANC Commissioner, current resident of Ward 2, and proud parent of 2 children.

Dan's leadership is central to OSSE's ongoing work to strengthen and modernize OSSE-DOT.