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 inefficiencies

Identify, prioritize, and deliver high‑impact AI use cases across underwriting, HR/recruitment, operations, and other core functions

Map existing workflows, systems, and data flows to identify opportunities for automation and optimization

Design 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 adoption

Establish and operationalize AI governance frameworks, including model risk management, auditability, vendor oversight, and data privacy standards

Partner with Operations, IT, Compliance, Legal, and Risk to ensure AI solutions are secure, explainable, and compliant

Define clear success metrics (e.g., reduction in manual effort, processing time, error rates) and track ROI across initiatives





Drive alignment across executive stakeholders, managing competing priorities and ensuring focus on highest‑impact initiatives

Lead internal enablement by increasing AI fluency across teams and ensuring successful adoption of deployed solutions

Oversee transition and knowledge transfer from external AI consultants, taking full ownership of ongoing initiatives

Stay current on emerging AI technologies and translate them into practical, high‑value business applications

Success in This Role Looks Like AI is embedded into day‑to‑day workflows across departments, not operating as standalone tools

Measurable improvements in efficiency, including reduced manual effort and faster processing times

Clear ownership, prioritization, and execution of AI initiatives across the organization

Robust alignment across executive stakeholders and cross‑functional teams

Established governance, controls, and auditability appropriate for a regulated financial environment

High adoption and trust of AI systems across business units

Qualifications &

Experience 8+ years of experience in transformation, operations, product, AI, or data‑driven roles

Proven 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 systems





Must have direct experience and domain expertise within financial services, specifically within Private Wealth, Mortgages, Investments, Private Equity, Wealth Management, or similar regulated financial operations

Strong understanding of financial services workflows, including document processing, decisioning systems, and risk/compliance constraints

Demonstrated ability to identify business problems and translate them into scalable AI solutions with measurable ROI

Experience working cross‑functionally with senior stakeholders, including executives

Strong process design, systems thinking, and change management capabilities

Experience establishing governance frameworks, including data privacy, model risk, auditability, and regulatory considerations

Core Competencies Strong bias toward execution with the ability to operate independently

Ability to move from ambiguity to structured, actionable plans

Excellent communication skills with the ability to clearly translate technical concepts into business value

Strong stakeholder management, including the ability to push back and prioritize effectively

Ownership mindset with a focus on outcomes and impact

Why 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 experience

Performance Bonus: 20–35% of base, tied to measurable AI adoption, efficiency gains, and ROI metrics

Benefits: Extended health & dental

Total On‑Target Earnings (OTE): CAD $210,000 – $300,000+

📌 Head of AI Enablement (Winnipeg)
🏢 Sage Recruiting
📍 Winnipeg