Fractional CIO Reports to: CEO (and collaborates closely with COO & Director of Ops) Location: Hybrid / On-site presence expected in Ontario Role Summary The Fractional CIO will lead the development, integration, and oversight of digital systems, operational technologies, and AI tools across a diverse portfolio of businesses, including aviation, hospitality, commercial real estate, cannabis retail, craft brewing, and international luxury charters.

This role will focus on identifying and deploying practical, scalable solutions to improve efficiency, reduce costs, and unlock data insights not theoretical AI applications.

Key Responsibilities 1.

Operational Technology Oversight Audit existing tech stacks across all entities (POS, inventory, finance, booking, staffing) Standardize platforms where possible; integrate data flows across business units Lead vendor selection and implementation (e.g., ERP, workforce management, POS) 2. AI and Automation Initiatives Identify low-friction, high-impact AI use cases: e.g., scheduling optimization, financial forecasting, vendor communication, reporting automation Collaborate with Director of Operations to embed AI-enhanced workflows Build or contract AI tools for real-time dashboards, performance analytics, or NLP-driven interfaces 3.





Digital Infrastructure Management Oversee IT security, data integrity, and backup policies Manage relationships with MSPs, cloud providers, and software vendors Ensure all technology is compliant with Canadian privacy and data regulations 4.

Cross-Functional Collaboration Partner with Finance on system integrations and reporting automation Partner with HR on payroll/benefits software and employee portals Support the Family Office in implementing secure and intelligent financial systems 5.

Long-Term Innovation Strategy Build a digital roadmap aligned with operational growth and owner priorities Stay abreast of emerging technologies relevant to Companys sectors Eventually build out an internal tech/analytics team or manage outsourced talent Ideal Candidate Profile 815 years in IT, product, or digital operations roles (ideally in multi-unit or service sectors) Robust systems integration experience (SaaS, POS, ERP, etc.) Experience working with or deploying Artificial Intelligence/AI-based tools (even lightweight solutions like ChatGPT for Teams, Power BI with Copilot, etc.) Capable of balancing long-term architecture with hands-on delivery Calm, methodical, collaborative able to work within a founder-led, evolving org

📌 Fractional CIO (North York)
🏢 Ward Technology Talent
📍 North York