Fractional Head of AI

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What the market looks like

Fractional Head of AI roles in Canada remain sparse — we've tracked 4 executive-level AI strategy postings in the last six months, concentrated in Toronto, Montreal, and Vancouver across technology, financial services, and professional services sectors. Organizations are increasingly comfortable with fractional leadership models for AI strategy, particularly during the exploratory and early-scaling phases. The strongest candidates bring prior experience building AI functions from the ground up, deep fluency with generative AI and large language models, and the ability to operate independently with minimal hand-holding. Compensation typically ranges from $250–$400 per hour depending on scope, industry, and strategic complexity.

Job responsibilities

• Develop and own the organization's AI strategy and transformation roadmap, including prioritization of use cases, technology stack, and implementation timelines

• Lead or advise on the build-out of an internal AI function, including hiring, team structure, and capability development

• Partner with the executive team and board to identify high-impact AI opportunities aligned with business priorities and competitive positioning

• Establish governance, risk, and compliance frameworks for responsible AI deployment and ethical decision-making

• Drive proof-of-concept projects and pilots to validate assumptions, reduce risk, and build organizational confidence in AI capabilities

• Coach internal leaders on AI literacy, strategy, and organizational readiness — translating technical concepts into business terms

• Stay current with AI/ML market developments and competitive landscape to inform strategy and keep the organization ahead of emerging risks and opportunities

Candidate requirements

• 5+ years in AI/ML strategy, AI product leadership, or AI/ML engineering roles — with demonstrated experience building or scaling AI functions or products

• Deep hands-on familiarity with generative AI, large language models, prompt engineering, and modern AI/ML tooling (both open-source and commercial)

• Proven ability to translate business problems into AI opportunities and lead cross-functional teams through strategy definition and execution

• Track record of operating independently with minimal structure — comfortable advising C-suite and boards without constant oversight

• Strong communication skills: able to explain complex AI concepts to non-technical audiences and influence decision-making at the executive level