Director of IT

Company OverviewCottage Dream Vacations (CDV) is a fast-growing hospitality and multi-industry company headquartered in Whitby, Ontario. We design, build, and operate luxury five-star cottage resorts across Canada. In addition to our resort division, CDV owns and manages a real estate training company, a cedar hot tub manufacturing business, and a gold mining operation.As we scale our digital platforms, expand resort locations, and unify technology across multiple industries, we are seeking a forward-thinking Director of Information Technology to lead our IT operations, enterprise systems, cloud infrastructure, and AI innovation efforts.Reporting directly to the VP of IT, this role is a cornerstone leadership position that shapes the technological future of CDV.Role SummaryThe Director of IT is responsible for the strategic leadership, architecture, implementation, and governance of all technology systems across CDV’s hospitality, training, manufacturing, and mining operations. This role blends enterprise IT leadership, hands-on systems engineering, AI strategy, ERP/CRM integration, and multi-site infrastructure management.The ideal candidate is an experienced IT leader who thrives at the intersection of hospitality systems, business software integration, AI-driven transformation, and enterprise cloud environments.Key Leadership ResponsibilitiesStrategic Leadership & Technology Vision

• Develop and execute a multi-year IT strategy aligned with CDV’s rapid growth and multi-industry expansion.
• Drive digital transformation initiatives across hospitality, manufacturing, real estate training, and mining.
• Present technology roadmaps, risks, and opportunities to the executive team and senior leadership.
• Establish IT governance practices, cybersecurity standards, and enterprise-wide technology policies.

Team Leadership & Department Management

• Lead, mentor, and grow a multidisciplinary team of IT professionals, developers, engineers, and support staff.
• Create performance KPIs, training plans, and standards of excellence for the IT department.
• Build a culture of innovation, accountability, and continuous improvement.
• Oversee vendor relationships, contracts, and technology partnership agreements.

Cross-Functional Collaboration

• Partner with operations, marketing, finance, hospitality management, and executive leadership to ensure alignment of technology with business objectives.
• Lead change management initiatives for new systems and upgrades.
• Provide high-level technical guidance and communication across all CDV departments.

Technical ResponsibilitiesIT Infrastructure, Networking & Server Management

• Architect, deploy, and manage both on-premise and cloud-based server environments (Google Cloud, AWS, Azure).
• Set up and maintain an in-house server room, ensuring data integrity, physical security, and high availability.
• Oversee network infrastructure across multiple resort and corporate locations, including LAN/WAN, VPNs, firewalls, wireless systems, and load balancing.
• Manage scaling, redundancy, backups, and disaster recovery frameworks.

Hospitality Technology & Multi-Property Systems

• Lead the architecture and optimization of property management systems (PMS), booking engines, POS integrations, guest check-in systems, and Wi-Fi networks.
• Oversee technology solutions that enhance guest experience, internal operations, and multi-property coordination.
• Implement smart-property and IoT devices to improve automation and efficiency across resort locations.

ERP & CRM Integration Leadership

• Lead the design, selection, and implementation of a unified ERP system tailored to CDV’s needs.
• Integrate ERP with CRM, finance, inventory, manufacturing, and operations for real-time business insights.
• Manage CRM configurations and integrations (Go HighLevel, HubSpot, Salesforce, or similar).
• Ensure seamless data flow between hospitality, sales, manufacturing, and operational systems.

Software & Systems Integration

• Oversee integration of all business applications, APIs, automations, and internal tools.
• Develop scalable system workflows that automate internal and guest-facing processes.
• Collaborate with department leaders to analyze needs and architect technical solutions.
• Ensure third-party and custom applications integrate efficiently into the broader technology ecosystem.

Advanced WordPress & Web Systems

• Direct development and maintenance of high-performance WordPress systems for CDV’s hospitality, training, and corporate brands.
• Oversee custom themes, plugins, API-based systems, and platform optimizations.

AI Systems Engineering & Innovation

• Lead CDV’s AI strategy and ensure ethical, secure deployment of AI-driven tools.
• Architect AI-powered systems for guest service automation, predictive analytics, operational efficiencies, and internal workflow automation.
• Develop and integrate AI applications into CRM, WordPress, booking platforms, and internal systems.
• Guide AI pilots and monitor ROI, adoption, and long-term scalability

Database Architecture & Data Governance

• Oversee database design, management, optimization, and scaling (SQL, NoSQL, Firebase, BigQuery).
• Ensure data quality, governance, compliance, and reporting accuracy across all divisions.
• Develop enterprise analytics dashboards that drive decision-making across CDV.

Process Automation & Workflow Optimization

• Analyze business operations across all divisions to identify opportunities for efficiency.
• Build automated workflows using modern automation tools (Zapier, Make, n8n, Power Automate).
• Ensure standardization, reliability, and documentation for all enterprise workflows.

Security, Compliance & IT Governance

• Develop and enforce cybersecurity policies, threat mitigation strategies, and access controls.
• Oversee infrastructure hardening, encryption, monitoring, and incident response.
• Ensure compliance with all security frameworks and international data protection regulations (GDPR, CCPA, PIPEDA).
• Conduct regular audits, penetration testing, and vulnerability assessments.

Project Management & Delivery

• Lead major IT initiatives from concept through deployment, ensuring delivery on time and within scope.
• Coordinate cross-departmental resources and third-party vendors.
• Implement project management best practices using tools such as Jira, Asana, or Trello.

Qualifications & RequirementsExperience & Expertise

• 7–10+ years in IT leadership, systems engineering, or enterprise technology roles.
• 2–5+ years leading technical teams or managing an IT department.
• Proven experience integrating CRM, ERP, PMS, and enterprise-level business systems.
• Strong background in server management (on-premise + cloud), networking, and multi-site infrastructure.
• Advanced experience with automation, APIs, and full-stack development (Java, Python, PHP, JavaScript preferred).
• Knowledge of hospitality technology systems is an asset.

Technical Proficiencies

• Cloud Platforms: Google Cloud, AWS, Azure
• CRM Systems: GoHighLevel, HubSpot, Salesforce
• ERP Systems: SAP, Oracle, Microsoft Dynamics, or similar
• Databases: SQL, MySQL, PostgreSQL, MongoDB, Firebase
• Network & Security: Cisco, Fortinet, Palo Alto, firewalls, VPNs
• Automation Tools: Zapier, Make (Integromat), Power Automate
• Project Tools: Jira, Asana, Trello

Education & Certifications (Preferred)

• Bachelor’s degree in IT, Computer Science, Engineering, or related field
• Certifications in Google Cloud, AWS, cybersecurity, or AI/ML
• Project Management certifications (PMP, Scrum) are an asset

Leadership Qualities

• Excellent communication and cross-functional collaboration skills.
• Ability to manage multiple high-priority initiatives simultaneously.
• Strong problem-solving and strategic-thinking abilities.
• Demonstrated success leading digital transformation efforts in complex environments.

What We Offer

• Starting Salary: $100,000–$110,000 (commensurate with experience)
• Paid time off & comprehensive benefits package
• Onsite parking
• A fast-paced, innovative work culture
• Succession planning and ongoing opportunities for career advancement
• Direct influence on shaping CDV’s technology, AI strategy, and multi-industry digital operations

Requests for accommodations can be made to [email protected] at any stage during the recruitment process.