Fractional CIO

Confidential • North York, Ontario, Canada • Posted March 17, 2026

Location North York, Ontario

Job Type Contract

Category Computer Occupations

Posted March 17, 2026

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 sel...
            

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