Lead CDL Driver

Create Your Experience of a Lifetime!

Come work and play in the mountains! Whether it’s your first-time seeing snow or you were born on the slopes, joining our team means discovering (or re-discovering!) a passion for the outdoors while building lifelong connections with teammates and guests from around the world.

With 40+ resorts across 3 continents, you can join our team for a season or stay to build a career. From day one, you'll receive some of the highest compensation rates in the industry, free pass(es) along with free ski and snowboard lessons, 40% retail discounts, the chance to grow through Epic Service - our leading training and development experience, and wellness benefits to fuel your success.

Hiring for our seasonal positions occurs on a rolling basis. Applications will be accepted until December 15th or until the positions are filled (whichever is first).

Employee Benefits

• Ski/Mountain Perks! Free passes for employees, employee discounted lift tickets for friends and family AND free ski lessons 
• MORE employee discounts on lodging, food, gear, and mountain shuttles
• 401(k) Retirement Plan 
• Employee Assistance Program
• Excellent training and professional development
• Referral Program

To Learn More, please review the Benefits Eligibility Summary

Job Summary:

The Breckenridge Ski Resort Transportation Department is seeking a motivated, safety-focused, and self-driven Transportation Lead to help develop and support a high-performing team of professional bus drivers. This is a key leadership position responsible for ensuring safe, reliable, and exceptional transportation service for our guests traveling between resort parking areas, lodging locations, and the ski resort via our resort bus network.

Transportation Lead plays an important role in delivering a seamless transportation experience that supports the overall guest journey. This position promotes a culture of safety, accountability, teamwork, and service.

Working closely with department management and fellow leads, the Transportation Lead supports daily bus operations, driver development, route planning, dispatch functions, and safety initiatives. This role provides opportunities to influence operational decisions, lead training efforts, mentor team members, and identify improvements that enhance both the guest and employee experience.

Job Specifications: 

• Starting Wage: $25.45/hr - $33.93/hr 

• Employment Type: Winter Seasonal 2026/2027

• Shift Type: Full Time hours available 

• Minimum Age: 21 years

• Housing Availability: Yes

Job Responsibilities:

• Open and/or close duties for transportation operations.
• Lead daily driver meetings and communicate operational updates.
• Support and train new CDL bus drivers.
• Support compliance with company policies, DOT regulations, and FMCSA requirements.
• Dispatch buses and adjust service based on guest demand, traffic conditions, weather, and operational needs.
• Coordinate transportation services between resort parking facilities and resort bus routes.
• Drive buses as needed to maintain service levels.
• Respond to operational issues, guest concerns, and service disruptions.
• Coach and support drivers while maintaining a professional and accountable work environment.
• Coordinate vehicle fueling, cleanliness, and maintenance needs with Fleet Maintenance.
• Assist with seasonal planning, special events, and peak operational periods.
• Perform additional duties as assigned.

Success in this role:

• Safe and efficient transportation operations.
• Reliable bus service that supports guest access to the resort.
• Well-trained drivers operating in compliance with DOT and company standards.
• Strong communication and teamwork across the Transportation Department.
• Quick response to operational challenges and changing business needs.

Job Requirements:

• Must be at least 21 years of age.
• Valid CDL B with Passenger Endorsement Driver's License with a satisfactory driving record in accordance with Vail Resorts Driver Policy and DOT Regulations.
• High School Diploma or equivalent.
• Excellent organizational, interpersonal, and communication skills.
• Strong work ethic with the ability to work independently and make sound decisions.
• Passion for delivering exceptional guest service.
• Interest in professional development and leadership growth opportunities.
• Ability to pass a post-offer background check.
• Ability to pass pre-employment and random drug screenings

Preferred:

• Minimum of two years operating commercial passenger vehicles.
• OR a minimum of two years of leadership experience as a Team Lead, Supervisor, or similar role.
• Working knowledge of DOT regulations, FMCSA compliance requirements, driver logs, and vehicle inspections.
• Experience dispatching vehicles and coordinating transportation operations during periods of high traffic volume in a high paced environment.

The expected pay range is $25.45/hr - $33.93/hr. This is the pay range we reasonably expect to pay for this position. Individual compensation decisions are based on a variety of factors.

In completing this application, and when submitting related documentation, applicants may redact information that identifies their age, date of birth, and/or dates of attendance at or graduation from an educational institution. 

We follow all federal, state, and local laws including restrictions on child/minor labor. Minors hired into this position will not be asked or permitted to engage in any activities restricted to adult workers.

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 517793
Reference Date: 09/23/2026 
Job Code Function: Commercial Driving (CDL Required)