Vail promotes from within for parking and transit operations managers |

Vail promotes from within for parking and transit operations managers

The town of Vail has promoted two former supervisors in the Public Works/Transportation Department to newly created manager positions. Stephanie Kashiwa has been named parking operations manager, while Jordan Winters is the new transit operations manager. The promotions were announced by department Director Greg Hall.

Stephanie Kashiwa

The new manager positions were created following the retirement of long-time Transit and Parking Manager Mike Rose earlier this year. To accommodate the growth in transportation operations and responsibilities, the former position was split into parking and transit functions.

Jordan Winters

Kashiwa has worked for the town since 2018 when she was hired as a parking supervisor. Her previous experience included working as resort operations manager for Vail Mountain in which she oversaw seven departments, including base area operations. She had been serving in an interim parking manager capacity with the town following Rose’s retirement.

In her new role, Kashiwa is helping to lead an effort to select a vendor who will upgrade Vail’s current parking system with state-of-the-art technology. She says installation of a new parking system is a great opportunity to focus on guest experience as well as identify operational efficiencies.

As the new transit operations manager, Winters brings a 14-year track record to the position having served in nearly all functions within Vail Transit. He has been a bus supervisor for seven years, a member of the Town of Vail Retirement Board, Safety Committee member, Event Review Committee member and acting transit manager for the past eight months.

Support Local Journalism

Winters helped launch the RideVail transit operations management system and is overseeing the transition to electric buses as the town works to transition 100% of its 33 buses to a clean energy fleet by the year 2032.

“The town is very fortunate to have such highly qualified employees as Steph and Jordan within our organization,” said Hall in a town release. “For the past six months, they took on the additional responsibilities of filling the acting manager roles, as well as their on-going job functions, and performed very successfully. The town looks forward to their leadership into the future as the world of transportation and mobility is a quickly and ever changing environment.”

To contact Kashiwa about the town’s parking operations, call 970-479-2445 or email To contact Winters about the town’s transit initiatives, call 970-479-2349 or email

Support Local Journalism