Job description

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 IT Field Services Regional Director develops and leads Field IT across an assigned region to execute strategy, drive business success, improve technology delivery and efficiency, and create an excellent employee experience. The role is accountable for regional support, service delivery, project execution, leadership effectiveness, workforce capability, financial stewardship, and operational performance. Reporting to the Field IT Sr. Director, the Regional Director helps shape Field IT priorities, roadmaps, operating models, and enterprise improvements, then translates them into coordinated regional execution. The role works successfully with the Field IT Extended Leadership Team (Field IT ELT), business leaders, and enterprise technology teams to align priorities, influence decisions, and deliver practical, scalable solutions. This leader develops Field IT leaders and organizational capability while fostering a safe, positive, inclusive, and high-performing culture. Success requires enterprise thinking, disciplined execution, strong cross-functional influence, financial and technical acumen, and commitment to employees, guests, and business outcomes. Job Specifications: • Starting Wage: $145,000.00 + Annual bonus + Equity • Employment Type: Year Round • Shift Type: Full Time hours available • Minimum Age: At least 18 years of age • Housing Availability: No Job Responsibilities: Regional Leadership and Strategy Execution • Lead Field IT operations, service delivery, projects, and people leadership across the assigned region. • Establish regional priorities, operating rhythms, decision rights, measures, and accountability aligned with Field IT and company strategy. • Partner with the Field IT Sr. Director to develop, refine, communicate, and execute Field IT strategy, roadmaps, and operating plans. • Translate strategy into coordinated regional objectives, initiatives, resource plans, and leader accountabilities. • Lead selected strategic initiatives from ideation and planning through adoption, measurement, and sustained operations. IT ELT and Business Partnership • Contribute effectively to IT ELT priorities, decisions, and shared outcomes while representing Field IT capabilities, capacity, risks, dependencies, and business context. • Build trusted relationships with IT directors, senior business and resort leaders, enterprise teams, and vendors. • Connect Field IT leaders and subject-matter experts with enterprise teams to shape integrated, supportable, and scalable solutions. • Guide multi-year regional technology roadmaps aligned with business needs, Field IT priorities, enterprise architecture, and information security. • Create transparency around demand, capacity, investments, risks, tradeoffs, and delivery commitments. Support, Service, and Project Delivery • Own reliable, consistent, business-aligned regional support and service outcomes. • Lead project and program governance with clear scope, ownership, schedule, budget, quality, risk management, adoption, and business outcomes. • Use service, project, customer, financial, workforce, and operational measures to improve performance and accountability. • Balance operational demand, seasonal readiness, strategic commitments, and project portfolios through transparent capacity and prioritization practices. • Anticipate and escalate material risks, dependencies, service concerns, and resource conflicts with clear recommendations. Efficiency and Organizational Excellence • Simplify work, reduce duplication, increase consistency, and scale effective solutions across Field IT. • Sponsor best-practice groups, communities of practice, and centers of excellence that strengthen shared standards, playbooks, tools, controls, and measures. • Promote standardization where it improves quality and efficiency while recognizing legitimate regional or local requirements. • Use data, feedback, benchmarking, and lessons learned to improve services, processes, technology, and operating models. People Leadership and Employee Experience • Create an excellent employee experience and a safe, positive, inclusive, respectful, and high-performing regional culture. • Lead and develop Sr. Managers, Managers, and other Field IT leaders through clear expectations, coaching, feedback, recognition, and accountability. • Build leadership depth through workforce planning, succession planning, talent reviews, mentoring, stretch opportunities, and intentional development. • Act on employee feedback to improve communication, inclusion, development, workload practices, engagement, and team connection. • Balance coverage, operational needs, projects, and employee well-being through responsible staffing and sustainable workloads. Financial, Workforce, Risk, and Vendor Leadership • Lead regional operating and capital planning, forecasting, purchasing, and financial performance. • Align structure, staffing, skills, capacity, and investments with current demand and future strategy. • Oversee vendors and contracts with accountability for service, cost, risk, performance, and value. • Proactively manage information security, compliance, privacy, safety, continuity, documentation, controls, and operational risk. Job Requirements: Required • 5+ years of progressively responsible technology leadership experience, including leadership of managers and geographically distributed teams. • Demonstrated success executing strategy, leading service delivery and complex initiatives, and delivering measurable organizational outcomes. • Ability to influence and collaborate with director-level and executive leaders across IT and the business. • Strong people leadership experience, including leader development, succession planning, organizational design, and employee engagement. • Strong business, financial, portfolio, capacity, vendor, risk-management, and executive communication skills. • Understanding of enterprise and field technologies, production support, information security, compliance, and high-availability service delivery. • Ability to travel within the assigned region and to other company locations as business needs require. Preferred • Education or equivalent experience in business, technology, information systems, organizational leadership, or a related field. • Experience in resort, hospitality, retail, or another geographically distributed and operationally complex business. • Experience leading centers of excellence, shared-service improvement, enterprise governance, or large cross-functional initiatives. • Strong understanding of enterprise and operational technologies and experience with organizational change and operating-model design. The expected Total Compensation for this role is $145,000.00 + Annual 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 where employees living within 50 miles of the Broomfield office work on-site Tuesday, Wednesday, Thursday and have flexibility to work off-site on Mondays and Fridays. Employees living outside of a commutable distance can work remotely from British Columbia, Washington D.C., and the 16 U.S. states* in which we currently operate. This includes: California, Colorado, Indiana, Michigan, Minnesota, Missouri, New Hampshire, New York, Nevada, Ohio, Pennsylvania, Utah, Vermont, Washington State, Wisconsin, and Wyoming. 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 518476 Reference Date: 10/24/2026 Job Code Function: Infrastructure

Requirements

Must-haves

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).
Employment Type: Year Round
Shift Type: Full Time hours available
Minimum Age: At least 18 years of age
Housing Availability: No
Regional Leadership and Strategy Execution
Lead Field IT operations, service delivery, projects, and people leadership across the assigned region.
Establish regional priorities, operating rhythms, decision rights, measures, and accountability aligned with Field IT and company strategy.
Partner with the Field IT Sr. Director to develop, refine, communicate, and execute Field IT strategy, roadmaps, and operating plans.
Translate strategy into coordinated regional objectives, initiatives, resource plans, and leader accountabilities.
Lead selected strategic initiatives from ideation and planning through adoption, measurement, and sustained operations.
IT ELT and Business Partnership

Nice-to-haves

Starting Wage: $145,000.00 + Annual bonus + Equity
Education or equivalent experience in business, technology, information systems, organizational leadership, or a related field.
Experience in resort, hospitality, retail, or another geographically distributed and operationally complex business.
Experience leading centers of excellence, shared-service improvement, enterprise governance, or large cross-functional initiatives.
Strong understanding of enterprise and operational technologies and experience with organizational change and operating-model design.
The expected Total Compensation for this role is $145,000.00 + Annual 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
Excellent training and professional development
Full Time roles are eligible for the above, plus:
Free ski passes for dependents

Application prep

Use the role’s language and application details while tailoring your materials.

Platform: successfactors
Effort: medium

Benefits

Benefits detected in the listing.

Health Insurance

Dental

Vision

401(K)

Professional Development