Fractional CIOWard Technology Talent Inc. • Hybrid, ON

Fractional CIO

Ward Technology Talent Inc. • Hybrid, ON

30+ days ago

Job type

Full-time

Job description

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 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)

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 delivery

Calm, methodical, collaborative — able to work within a founder-led, evolving org

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Fractional CIO • Hybrid, ON

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