Sr. Director, Enterprise Technology and AI Transformation

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 Sr. Director, Enterprise Technology & AI Transformation is a senior business leader responsible for identifying and leading opportunities to fundamentally improve how work gets done across Vail Resorts. This leader connects business strategy, process transformation, technology, automation, and AI to deliver measurable business outcomes.

As a member of the Transformation Management Office, this role defines and leads the enterprise process and AI transformation roadmap, identifying the highest-value opportunities, business cases, investment needs, and measurable outcomes required to advance enterprise goals. The Sr. Director partners with executive and functional leaders to identify opportunities, redesign end-to-end workflows, simplify and standardize work, and scale technology and AI solutions from ideation through scaled adoption and value realization.

The role operates in a business-led, IT-governed model. With the process owners and functional leaders, co-owns the business problem, transformation opportunity, process and operating model design, business case, technology or AI pathway decision and realized business value. IT owns how solutions are architected, built, secured and supported.

Job Responsibilities:

Identify & Prioritize Opportunities

• Assess opportunities to determine where work should be eliminated, simplified, standardized, optimized, automated, or enabled by AI. Baseline process performance to measure future value.
• Quantify value, investment requirements, feasibility and dependencies to develop and prioritize the transformation portfolio
• Establish an enterprise pipeline of transformation opportunities through business engagement, operational insights, and process analysis.

Design Future-State Work

• Lead the redesign of complex, end-to-end processes and workflows, challenging existing ways of working and identifying opportunities to improve efficiency, effectiveness and scalability.
• Define future-state processes, capabilities and requirements in partnership with functional leaders and relevant technology partners.

Lead the Technology Transformation Portfolio

• Develop and evolve enterprise standards, methods and tools for process and AI transformation, including establishing portfolio governance, prioritization, and performance measures across technology transformation initiatives from business case through implementation.
• Support translating business and process opportunities into clear technology, automation and AI requirements and pathways.
• Partner with IT to evaluate solution options, sequence investments and ensure solutions align with technology/AI architecture and address the intended business outcomes.
• Stay current on emerging AI and automation capabilities and identify practical applications with enterprise value.

Drive Adoption & Sustained Value

• Partner with functional leaders to embed new processes, technologies and ways of working into the business.
• In partnership with Global Shared Services, establish accountability, performance measures and continuous-improvement mechanisms to sustain transformation benefits

Job Requirements

• 10+ years of progressive experience leading enterprise transformation, business process transformation, operational improvement, technology-enabled transformation or a related discipline, including experience leading complex, cross-functional initiatives at an enterprise level.
• Demonstrated ability to identify and prioritize opportunities to improve efficiency, simplify work, optimize processes, and apply automation or emerging technology to deliver measurable business outcomes.
• Deep expertise in end-to-end process design, process optimization and operating model transformation, with the ability to translate complex business problems into practical future-state solutions.
• Strong business and financial acumen, including experience developing business cases, assessing investment tradeoffs, sizing value opportunities and measuring realized benefits.
• Strong understanding of AI, automation and enterprise technology capabilities and their practical application to business processes; deep technical or AI engineering expertise is not required.
• Proven ability to lead through influence across functions and organizational boundaries, build alignment among executive/senior leaders, and navigate complex decisions and competing priorities.
• Demonstrated experience leading organizational change and driving adoption of new processes, technologies and ways of working to achieve defined business and financial outcomes.
• Exceptional executive communication and facilitation skills, with the ability to simplify complex concepts, frame decisions and influence action at the senior leadership level.
• Bachelor's degree in business, technology, engineering, operations or a related field; advanced degree preferred.

The expected Total Compensation for this role is $175,000 - $200,000 + 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 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  518291
Reference Date: 10/13/2026 
Job Code Function: HR Shared Services