Senior Manager, Legal Technology, Operations & AI Enablement

Responsibilities

• Build and lead a high-performing legal operations team with clear direction, performance management, and organizational capacity.
• Develop and drive an AI enablement program, including evaluating and deploying AI-powered tools, embedding them into attorney workflows, reducing manual legal work through agentic automations, and upskilling legal professionals.
• Execute and scale legal and business operations initiatives, including go-to-market strategies, CPQ implementations and enhancements, and Ironclad workflows.
• Improve contract lifecycle management systems and cross-system integrations in collaboration with procurement, accounting, HR, sales, deal desk, IT, and engineering.
• Generate operational savings through Oracle, Zip, Salesforce, and Workday integrations with CLM and procure-to-pay workflows.
• Manage outside counsel operations, including billing guidelines, e-billing systems, law firm evaluations, and spend reporting.
• Build and maintain knowledge management infrastructure and KPI dashboards that provide visibility into operational health.
• Lead change management to drive adoption of new technology and processes across a distributed legal function.

Requirements

• 8+ years of experience in legal operations, strategy and operations, or a related field, including ownership of a legal operations program.
• At least 3 years of direct people management experience.
• Experience leading at least two end-to-end technology implementations with deep systems integrations.
• Hands-on experience owning AI tooling, evaluating vendors, deploying tools, and building or managing AI-assisted or agentic workflows.
• Strong analytical and project management skills, with the ability to manage multiple complex initiatives simultaneously.
• Excellent communication and stakeholder management skills, including collaboration across legal, policy, finance, IT, and business teams.

Nice-to-haves

• Experience in a high-growth or recently public technology company with a complex, multi-jurisdictional operational footprint.
• Exposure to marketplace or platform businesses.
• Experience designing agentic or automated legal workflows and building solutions before adopting off-the-shelf tools.
• Familiarity with legal operations communities such as CLOC.
• Experience conducting vendor RFPs or law firm evaluations focused on outside counsel cost discipline.

Compensation and Benefits

• Canadian base pay range: CAN$149,000–$157,000 CAD.
• Eligible for a new-hire equity grant and annual refresh grants.
• Competitive compensation and benefits based on work location, experience, and required skills.
• Remote role for candidates permanently located in Ontario, Alberta, British Columbia, or Nova Scotia.