Winsport

Born from the legacy of the 1988 Winter Olympic Games, WinSport is more than a place — it is a spirit that ignites potential. As a not-for-profit organization and the proud owner and operator of Canada Olympic Park, WinSport provides inclusive opportunities for Canadians to discover, develop, and excel at sport and physical activity through world-class training, legendary facilities, and exceptional experiences. Through year-round sport, entertainment, recreation, and shared experiences, WinSport brings people together and creates spaces where belonging thrives.

The Director, Information Technology is a key leadership role where you will have the opportunity to shape WinSport’s technology strategy, strengthen infrastructure and cybersecurity, and support the continued modernization of a dynamic, multi-building campus. Reporting to the Chief Financial Officer and serving as the primary IT advisor to the Executive Leadership Team, you will lead a shared service function that supports high-volume, public-facing operations, including more than one million annual guest visits, approximately $35M in annual revenue, and a workforce that scales seasonally from approximately 150 to 800 team members.

This is a pivotal leadership role for a strategic, hands-on technology leader who understands that reliable, secure, and well-integrated systems are essential to exceptional guest, athlete, employee, and event experiences. As a trusted advisor to the CFO and Executive Leadership Team, you will lead the development and execution of a pragmatic IT roadmap, oversee core operational systems, strengthen cybersecurity and risk management practices, and ensure the stability of revenue-impacting technologies across point-of-sale, ticketing, RFID access control, food and beverage, lessons and programs, and event operations.

The ideal candidate brings post-secondary education in Information Technology, Computer Science, or an equivalent combination of education and experience, along with 7+ years of progressive IT experience, including leadership across infrastructure, end-user services, and business applications in a lean environment. You have experience supporting high-availability, revenue-impacting environments such as hospitality, retail, attractions, venues, or event-based operations, and bring strong capability in network and endpoint management, cybersecurity fundamentals, vendor and MSP oversight, and executive communication.

Join a leadership team that is building on an Olympic legacy while shaping the future of sport, recreation, and community connection in Calgary. At WinSport, you will help strengthen the systems, tools, and technology foundations that enable safe, seamless, and memorable experiences for guests, athletes, employees, partners, and the broader community.

Janet Soles and Associates has been retained to conduct this search on behalf of WinSport. For more information about this opportunity or to apply, please send your curriculum vitae and letter of interest with the Subject Line – “WinSport Dir IT” in confidence to apply@jssearch.ca.