Company Description Cottage Dream Vacations is a cottage-focused resort developer and operator in Canada, specializing in unique, experience-driven hospitality offerings. The company is building a strong presence in the sector, with over five resorts nationwide in various stages of development. Team members contribute to shaping modern cottage resort experiences for guests while supporting sustainable growth.

Joining Cottage Dream

Vacations offers the opportunity to work in a dynamic environment that values innovation, operational excellence, and collaborative problem-solving.

Role Description The Director of Information Technology is a full time, on-site role based in Toronto, ON, responsible for leading the overall IT vision, strategy, and operations for Cottage Dream Vacations. This role oversees the planning, implementation, and maintenance of technology systems across current and developing resort properties, including infrastructure, applications, and security controls. Day-to-day responsibilities include managing IT staff and vendors, monitoring system performance, ensuring network and data security, and aligning IT initiatives with business objectives.

The Director will collaborate with executive leadership and cross-functional teams to support digital transformation, improve operational efficiency,



and ensure reliable technology support for resort operations and corporate functions.

Qualifications

Candidates should possess strong skills in IT Management and IT Operations to oversee systems, teams, budgets, and vendor relationships.

Candidates should possess deep knowledge of Information Technology across infrastructure, applications, and cloud or hybrid environments.

Candidates should possess expertise in Network Security to safeguard data, manage access controls, and ensure compliance with security standards.

Candidates should possess experience in IT Strategy, including long-term technology planning, roadmap development, and alignment with business goals.

Relevant qualifications include prior leadership experience in an IT director or similar role, preferably in hospitality or multi-site operations.

Bachelor’s degree in Information Technology, Computer Science, or a related field; advanced certifications (e.g., ITIL, CISSP, PMP) are an asset.

Strong communication, stakeholder management, and change management skills, with the ability to collaborate effectively at all organizational levels.

Demonstrated ability to manage complex projects, implement new systems, and drive continuous improvement in IT processes and services.

📌 Director of Information Technology (Toronto)
🏢 Cottage Dream Vacations
📍 Toronto