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.
Responsibilities  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)
AI and Automation Initiatives   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
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
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
Long-Term Innovation Strategy   Build a digital roadmap aligned with operational growth and owner priorities
Stay abreast of emerging technologies relevant to Company’s sectors
Eventually build out an internal tech/analytics team or manage outsourced talent
Ideal Candidate Profile   8–15 years in IT, product, or digital operations roles (ideally in multi-unit or service sectors)
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

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