Director of Information Technology

About the role

The Director of Information Technology will shape WinSport’s technology strategy, strengthen infrastructure and cybersecurity, and support the modernization of a dynamic, multi‑building campus. Reporting to the CFO and advising the Executive Leadership Team, you will lead a shared‑service function that underpins more than one million annual guest visits and seasonal staffing of up to 800 employees.

Key responsibilities

• Develop and execute a pragmatic IT roadmap aligned with business goals.
• Oversee core operational systems, including point‑of‑sale, ticketing, RFID access control, and event‑operations platforms.
• Strengthen cybersecurity and risk‑management practices across the organization.
• Manage network, endpoint, and infrastructure services to ensure high availability.
• Provide vendor and MSP oversight, negotiating contracts and monitoring performance.
• Serve as the primary IT advisor to the CFO and Executive Leadership Team.

Required profile

• Post‑secondary education in Information Technology, Computer Science, or equivalent.
• 7+ years of progressive IT experience, including leadership of infrastructure, end‑user services, and business applications.
• Experience in high‑availability, revenue‑impacting environments such as hospitality, retail, attractions, or event venues.
• Strong executive communication skills and ability to influence senior stakeholders.

Required skills

• Network management
• Endpoint management
• Cybersecurity fundamentals
• Vendor management
• MSP oversight