Our mission is to create the Experience of a Lifetime for our employees, so they can, in turn, create the Experience of a Lifetime for our guests. We own and operate the most renowned destination resorts in the world as well as regional and local ski areas outside major cities, and connect them all through one unrivaled network. We are looking for ambitious leaders, innovators and creators to join our talented team. If you’re ready to pursue your fullest potential, we want to get to know you!

Candidates for year-round positions are reviewed on a rolling basis. Applications will be accepted up to 90 days after the posting date, or until the position is filled (whichever is first).

Job Summary:

The Director of Benefits leads the execution and continuous improvement of Vail Resorts’ North American benefits programs, including Health & Welfare, Retirement, Time Off plans and Perks. Reporting to the Vice President, Total Rewards, this role is responsible for delivering competitive, compliant, and cost‑effective benefits programs while contributing operational insight to the broader Total Rewards strategy.

As a member of the Total Rewards leadership team, the Director partners closely with the Vice President, Total Rewards to translate enterprise priorities into practical program design, operational plans, and measurable results. This role maintains direct accountability for day‑to‑day benefits delivery, vendor management, financial outcomes, and employee experience across the U.S. and Canada, while also informing longer‑term program direction through data, market insight, and execution expertise.

Job Specifications:

• Starting Wage: $160,000 - $180,000 + bonus + equity
• Employment Type: Year Round
• Shift Type: Full Time hours
• Minimum Age: At least 18 years of age
• Housing Availability: No

Job Responsibilities:

Program Design & Strategy Support

• In partnership with the Vice President, Total Rewards, contribute to benefits strategy and multi‑year planning by bringing forward operational insights, data analysis, and practical implications.
• Translate Total Rewards priorities into executable program designs, plan changes, and enhancements that balance cost, risk, and employee value.
• Use internal data, benchmarking, and market trends to inform recommendations and support decision‑making.

Benefits Program Execution & Operations:

• Lead the administration and delivery of benefits programs, including medical, dental, vision, life, disability, voluntary benefits, leave of absence, EAP, and retirement plans, ensuring accuracy, compliance, and a strong employee experience.
• Own annual renewal planning, open enrollment execution, and seasonal hire/rehire benefit readiness, with accountability for timelines, decisions, and outcomes.
• Ensure ongoing compliance with all applicable benefits regulations (e.g., ERISA, ACA, FMLA), proactively identifying risks and addressing issues.
• Provide direct oversight of benefits operations, systems, and vendor interactions, stepping in as needed to resolve issues and ensure consistent execution.

Financial Management & Vendor Oversight:

• Manage benefits‑related budgets, forecasts, and cost controls, with responsibility for monitoring trends and financial performance.
• Serve as the primary point of contact for benefits consultants, actuaries, insurers, and third‑party administrators; actively manage vendor performance, contracts, and issue resolution.
• Prepare materials and support governance activities for the 401(k) Administrative and Fiduciary Committees.

Collaboration & Leadership:

• Partner with the Director of Wellness to align benefits and well‑being programs and assess program effectiveness.
• Work closely with Employee Communications to develop and execute benefits‑related communications and change management activities.
• Collaborate with Compensation, HR Operations, Finance, Legal, and Strategic Business HR to ensure integrated Total Rewards delivery.
• Lead work through clear accountability, subject‑matter expertise, and effective collaboration across stakeholders.

Job Requirements:

• 5+ years of experience in Benefits, with experience leading a team
• Demonstrated ability to build programs and processes from scratch and/or see the potential for improvement in existing programs and processes
• Ability to connect with and lead others who do not directly report to you
• Ability to analyze data to inform strategies and tactics
• Ability to apply natural curiosity regarding business results and insights while consistently identifying ways to improve management and execution of key processes
• Financial acumen to design, deliver, and measure effectiveness of benefits plans
• Bachelor’s degree in business, human resources, or related field

Preferred:

• Prior leadership of in-house benefits administration a plus
• Advanced credential (e.g., CCP, SPHR) preferred

The expected Total Compensation for this role is $160,000 - $180,000 + bonus + equity. Individual compensation decisions are based on a variety of factors.

Job 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

Full Time roles are eligible for the above, plus:

• Health Insurance; Medical Insurance, Dental Insurance, and Vision Insurance plans (for eligible seasonal employees after working 500 hours)
• Free ski passes for dependents
• Critical Illness and Accident plans

Vail Resorts offers a ‘Hybrid’ work environment for Broomfield-based roles where employees must live within 50 miles of the Broomfield office and work on-site Tuesday, Wednesday, Thursday and have flexibility to work off-site on Mondays and Fridays.

Please note that the ability to work in person or off-site, and the particulars related to such work, are subject to change at any time; and, accordingly, the Company reserves the right to change its policies and/or require in-person/in-office work or off-site work at any time in its sole discretion.

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 513951
Reference Date: 03/18/2026
Job Code Function: Benefits