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Transportation Supervisor - Full Time - Year Round

Date:  Jun 7, 2021

Keystone, CO, US

Company:  Keystone Resort
Shift Type:  Year Round

Reach Your Peak at Vail Resorts.  As a community of adventurers and discoverers, Vail Resorts delivers an experience of a lifetime to our guests and our employees. Our team is made whole by the brave, passionate individuals who ambitiously push boundaries and challenge the status quo. Whether you’re looking for seasonal work or the career of a lifetime, join us today to reach your peak. 

As a Transportation Team Lead for Keystone Resort, you will supervise a team of up-to 70 drivers and navigate the daily challenges of our diverse operations. During the winter, Team Leads will be responsible for greeting drivers, completing time and labor, keeping up-to-date driver files, adjusting the schedule, monitoring dial-a-ride and fixed-route shuttle operations, coordinating bus rotation with the vehicle maintenance team, and providing any necessary support to the drivers to ensure a smooth operation. In the summer, Team Leads will be primarily communicating with prospective clients to organize wedding transportation, drafting service contracts, overseeing dial-a-ride and charter operations, and maintaining up-to-date driver and vehicle records. Team Leads will connect drivers to the department manager by communicating concerns and addressing safety issues at our weekly meeting. They will also discuss any changes or updates with the drivers during our weekly safety meetings. Team Leads will be expected to observe driver behavior, address safety concerns, provide performance feedback, and execute corrective action plans. They will coordinate with dispatch and other departments to accomplish tasks and overcome daily challenges and may be asked to drive as needed.


Responsibilities include, but are not limited to:

  • Monitor daily operations and guide drivers to successfully overcome the daily challenges of our transportation department
  • Serve as a role model for all drivers and a representative of the company by adhering to and supporting all company safety programs and initiatives
  • Observe and evaluate drivers’ operating behaviors and compliance with all company and federal regulations
  • Maintain up-to-date physical and electronic driver qualification files in accordance with local, state, and federal DOT guidelines
  • Complete Time & Labor daily/nightly
  • Create a schedule to meet our volume-based operational needs
  • Utilize computer dispatch to assign pick-ups and drop-offs
  • Initiate post-accident follow-up and executive corrective action retraining if necessary
  • Deliver performance feedback through ride-alongs and end of season reviews
  • Other duties as assigned to assist the department manager
  • Flexible working hours



  • Class B CDL with Passenger endorsement is required
  • At least 2 years minimum experience driving commercial vehicles
  • At least 1 year minimum supervisory experience
  • Must be 21 years of age or older
  • High School Diploma
  • Ability to communicate and work well with the public and others inside and outside of the department

The budgeted range starts at $20.00 - 32.40.  Actual pay will be adjusted based on experience.


The perks include a free ski pass, and a set of benefits including... 

  • Medical, Dental, Vision insurance, and a 401(k) retirement plan  
  • Hourly employees are generally eligible for accrued Paid Time Off (PTO), Extra Time Off (ETO) and Sick Time.  Salaried employees are generally eligible for Flexible Time Off (FTO) 
  • Paid Parental Leave for eligible mothers and fathers  
  • Healthcare & Dependent Care Flexible Spending Accounts  
  • Life, AD&D, and disability insurance 


We’re looking for team members who are passionate about their work and the world around them, who take pride in ensuring our guests receive the best possible service and who bring a sense of self and fun to all they do. Life at 9,280 feet in the sky is a little different. With our crisp Rocky Mountain air and boundless options for adventure and exploration, you can join a community who loves where they live and loves what they do. Keystone will be your home away from home; a place where friendliness, an eye for detail and unmatched guest service is the foundation of our Culture. Come join our team – where A Mountain of Possibilities awaits. www.vailresortscareers.com

Vail Resorts is an equal opportunity employer. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, sexual orientation, gender identity, disability, protected veteran status or any other status protected by applicable law.

Requisition ID 317269

Nearest Major Market: Denver