Fractional CIO
Job in
North York, Toronto, Ontario, M5A, Canada
Listing for:
Ward Technology Talent Inc.
Contract
position
Listed on 2026-01-01
Job specializations:
-
IT/Tech
Data Analyst, Data Science Manager
Job Description & How to Apply Below
Location: North YorkFractional 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 unitsLead 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 automationCollaborate with Director of Operations to embed AI-enhanced workflowsBuild or contract AI tools for real-time dashboards, performance analytics, or NLP-driven interfaces3. Digital Infrastructure Management
Oversee IT security, data integrity, and backup policiesManage relationships with MSPs, cloud providers, and software vendorsEnsure all technology is compliant with Canadian privacy and data regulations4. Cross-Functional Collaboration
Partner with Finance on system integrations and reporting automationPartner with HR on payroll/benefits software and employee portalsSupport the Family Office in implementing secure and intelligent financial systems5. Long-Term Innovation Strategy
Build a digital roadmap aligned with operational growth and owner prioritiesStay abreast of emerging technologies relevant to Company’s sectorsEventually build out an internal tech/analytics team or manage outsourced talentIdeal Candidate Profile
8–15 years in IT, product, or digital operations roles (ideally in multi-unit or service sectors)Strong 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 deliveryCalm, methodical, collaborative — able to work within a founder-led, evolving org
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