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 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 CDVs 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 CDVs 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 CDVs 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 CDVs hospitality training and corporate brands.
• Oversee custom themes plugins API-based systems and platform optimizations.

AI Systems Engineering & Innovation

• Lead CDVs 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

• 710 years in IT leadership systems engineering or enterprise technology roles.
• 25 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)

• Bachelors 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: $100000$110000 (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 CDVs technology AI strategy and multi-industry digital operations

Requests for accommodations can be made to at any stage during the recruitment process.

Required Experience:

Director

Employment Type : Full-Time
Experience: years
Vacancy: 1
Monthly Salary Salary: 100000 - 110000