Senior Manager, Legal Technology, Operations & AI Enablement

Overview

A rapidly growing legal department within a technology-driven grocery delivery organization is seeking a Legal Operations Leader to build and manage the infrastructure, tooling, and team capabilities that enhance the legal function's efficiency, intelligence, and accountability. This role focuses on integrating legal operations, technology, and AI enablement to support new business models, advertising formats, and retail partnerships.

Responsibilities

• Build and lead a high-performing legal operations team with clear direction, performance management, and organizational support capacity.
• Develop and deploy an AI enablement program, including evaluating, implementing, and embedding AI-powered tools into attorney workflows to reduce manual legal work and upskill professionals.
• Execute and scale legal and business operations initiatives such as Go-To-Market strategies, CPQ implementations, and workflow enhancements supporting new ad formats and retailer engagements.
• Continuously improve contract lifecycle management (CLM) systems and cross-system integrations, collaborating with procurement, accounting, HR, sales, deal desk, IT, and engineering teams.
• Manage outside counsel operations with clear accountability, including enforcing billing guidelines, managing e-billing systems, completing law firm evaluations, and establishing spend reporting.
• Build and maintain the team's knowledge management infrastructure and develop KPI dashboards to provide leadership with clear visibility into operational health.

Requirements

• Minimum 8 years of experience in legal operations, strategy & operations, or a related field.
• At least 3 years of direct people management experience.
• Proven leadership of at least two end-to-end technology implementations with deep systems integrations (e.g., Ironclad, Zip, Salesforce, CPQ, Oracle, Workday, or comparable platforms).
• Hands-on experience owning AI tooling, evaluating vendors, deploying tools, and managing AI-assisted or agentic workflows.
• Strong analytical and project management skills capable of driving multiple complex initiatives simultaneously in a fast-paced environment.
• Excellent communication and stakeholder management skills with experience collaborating across legal, policy, finance, IT, and business teams.

Preferred Qualifications

• Experience in a high-growth or recently public technology company with a complex, multi-jurisdictional operational footprint, including marketplace or platform business exposure.
• Experience designing agentic or automated legal workflows with a preference for building custom solutions over off-the-shelf tools.
• Familiarity with legal operations communities or equivalent professional development.
• Experience conducting vendor RFPs or law firm evaluations focused on outside counsel cost discipline.
• Demonstrated ability to lead change management efforts to drive organizational adoption of new technology and processes across a distributed legal function.

Compensation & Benefits

• This is a remote role with compensation dependent on the candidate's permanent work location.
• Base pay range for Canadian candidates: $149,000—$157,000 CAD.
• Eligible for new hire equity grants and annual refresh grants.
• The organization offers highly competitive compensation and benefits tailored to each employee's location.

Location

• Remote position.
• Currently hiring only in the Canadian provinces of Ontario, Alberta, British Columbia, and Nova Scotia.

Candidates must be located in one of these provinces to be considered for this role.