Head Of Ai Enablement

The Head of AI Enablement is responsible for owning and executing the end-to-end AI transformation across the organization. This role is highly execution-focused and sits at the intersection of operations, technology, compliance, and change management.The successful candidate will take AI from fragmented pilots and siloed tools to fully embedded, governed workflows that drive measurable business outcomes. This is not a research or advisory role—it is a hands‑on leadership role focused on identifying operational bottlenecks, deploying AI solutions into production, and driving adoption across the business in a regulated environment.This individual will act as the internal owner of AI initiatives, working directly with executive stakeholders to prioritize, implement, and scale high‑impact use cases.Key Responsibilities
Own and execute the enterprise AI strategy and roadmap aligned to business priorities and operational inefficienciesIdentify, prioritize, and deliver high‑impact AI use cases across underwriting, HR/recruitment, operations, and other core functionsMap existing workflows, systems, and data flows to identify opportunities for automation and optimizationDesign and deploy AI‑powered workflows using LLMs, document intelligence, and automation tools (not just pilots—production systems)Embed AI into standard operating procedures (SOPs) to ensure consistent and scalable adoptionEstablish and operationalize AI governance frameworks, including model risk management, auditability, vendor oversight, and data privacy standardsPartner with Operations, IT, Compliance, Legal, and Risk to ensure AI solutions are secure, explainable, and compliantDefine clear success metrics (e.G., reduction in manual effort, processing time, error rates) and track ROI across initiativesDrive alignment across executive stakeholders, managing competing priorities and ensuring focus on highest‑impact initiativesLead internal enablement by increasing AI fluency across teams and ensuring successful adoption of deployed solutionsOversee transition and knowledge transfer from external AI consultants, taking full ownership of ongoing initiativesStay current on emerging AI technologies and translate them into practical, high‑value business applicationsSuccess in This Role Looks Like
AI is embedded into day‑to‑day workflows across departments, not operating as standalone toolsMeasurable improvements in efficiency, including reduced manual effort and faster processing timesClear ownership, prioritization, and execution of AI initiatives across the organizationStrong alignment across executive stakeholders and cross‑functional teamsEstablished governance, controls, and auditability appropriate for a regulated financial environmentHigh adoption and trust of AI systems across business unitsQualifications & Experience
8+ years of experience in transformation, operations, product, AI, or data‑driven rolesProven track record of implementing AI or automation solutions in production environments (not research‑focused)Hands‑on experience with AI technologies such as LLMs, workflow automation tools, and data‑driven systemsMust have direct experience and domain expertise within financial services, specifically within Private Wealth, Mortgages, Investments, Private Equity, Wealth Management, or similar regulated financial operationsStrong understanding of financial services workflows, including document processing, decisioning systems, and risk/compliance constraintsDemonstrated ability to identify business problems and translate them into scalable AI solutions with measurable ROIExperience working cross‑functionally with senior stakeholders, including executivesStrong process design, systems thinking, and change management capabilitiesExperience establishing governance frameworks, including data privacy, model risk, auditability, and regulatory considerationsCore Competencies
Strong bias toward execution with the ability to operate independentlyAbility to move from ambiguity to structured, actionable plansExcellent communication skills with the ability to clearly translate technical concepts into business valueStrong stakeholder management, including the ability to push back and prioritize effectivelyOwnership mindset with a focus on outcomes and impactWhy Join
This is an opportunity to take full ownership of AI transformation within a growing organization and build an enterprise AI capability from the ground up. You will work directly with executive leadership and have the ability to shape how AI is embedded into core business operations.Compensation
Base Salary: CAD $175,000 – $225,000, commensurate with experiencePerformance Bonus: 20–35% of base, tied to measurable AI adoption, efficiency gains, and ROI metricsBenefits: Extended health & dentalTotal On‑Target Earnings (OTE): CAD $210,000 – $300,000+
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