DIRECTOR OF IT

Job Description

Job Description

Description:

Overview of Position: The Information Technology Director is a key member of the senior leadership team, responsible for the vision, strategy, and execution of all technology initiatives at Windham Mountain Club. This role provides strategic leadership to the IT department and ensures the alignment of technology with the resort's business goals. The Director will oversee the entire IT infrastructure and key business systems, including the RTP One Point of Sale platform, to drive efficiency, innovation, and an exceptional guest and staff experience. Through strategic planning, robust analysis, and effective team leadership, the IT Director will guide the company's technological direction, manage vendor relationships, and ensure the security and stability of our digital environment.

Job Duties: The list below best represents many of the tasks you will be asked to perform at some time during your employment at Windham Mountain Club. This list of duties is not intended to be all-encompassing.

Strategic & Financial

• Develop, implement, and maintain the company’s long-term IT strategic roadmap, ensuring it supports business growth, operational excellence, and guest satisfaction.
• Create and manage system roadmaps for all critical business applications (POS, CRM, etc.), planning for upgrades, integrations, and replacements to meet future needs.
• Lead the IT department's annual budgeting and financial planning process, managing both capital and operational expenditures to maximize ROI.
• Serve as the primary technology advisor to the executive team, providing insights and recommendations on technology-related opportunities and risks.
• Champion digital transformation and innovation initiatives that enhance the guest experience and create a competitive advantage.

Leadership & Vendor Management

• Lead, mentor, and develop the IT team, fostering a culture of accountability, collaboration, and continuous improvement.
• Direct all vendor management activities, including the evaluation, selection, and negotiation of contracts with software, hardware, and service providers to ensure optimal terms and value.
• Oversee the management of key technology partners, holding them accountable for service level agreements (SLAs) and performance.
• Perform supervisory duties for the IT department, including performance management, hiring, and professional development.

Operational & Technical Oversight

• Direct the management and administration of the resort’s multi-site network environment, ensuring its stability, security, and scalability.
• Oversee the company’s cybersecurity strategy, including the management of firewalls, endpoint protection, and incident response to protect corporate and guest data.
• Ensure robust backup and disaster recovery plans are in place and tested regularly.
• Oversee the administration and strategic direction for key systems, including RTP, Aspenware, and financial software.
• Ensure ongoing compliance with all relevant regulations and standards.
• Maintain comprehensive documentation of IT systems, policies, and procedures.

Work Schedule and Conditions: We are in the business of providing a premier product and experience for our guests. Traditionally our busy periods are during weekends and holiday periods which you will be expected to work. You can also expect to be asked to work extra hours or days on occasion to support key initiatives and operational needs.

• Bachelor’s degree or higher in Computer Science, Information Systems, or related field.
• Minimum 8-10 years of progressive experience in IT, with at least 3-5 years in a leadership or senior management role, preferably within the hospitality or ski resort industry.
• Proven experience in developing and executing IT strategic roadmaps that align with business objectives.
• Strong background in managing enterprise-level POS and E-commerce platforms; direct experience with Resort Technology Partners (RTP) is highly preferred.
• Demonstrated expertise in vendor management, including contract negotiation, and building strategic partnerships.
• Expert knowledge of IT infrastructure, cybersecurity principles, network architecture, and data governance.
• Extensive experience with IT budgeting, financial planning, and asset management.
• Exceptional leadership, communication, and interpersonal skills, with the ability to influence and communicate complex technical concepts to non-technical stakeholders and executive leadership.
• Strategic mindset with a passion for innovation and staying current on emerging technology trends in the hospitality and ski space.
• Demonstrated experience leading and mentoring high-performing technical teams.