Head of Legal Outsourcing Services

Sterlington, PLLC • Toronto, ON

3h • Remote

About The Position

Sterlington PLLC is a full-service law firm focusing on complex corporate, litigation, executive compensation, and private wealth matters. The Firm operates a globally distributed outsourcing function of approximately fourteen professionals, most of whom are qualified lawyers with LLM credentials in their respective jurisdictions. This team drafts and reviews non-disclosure agreements at scale in support of the Firm's private equity and equity-focused client base. The successful candidate will assume full ownership of the outsourcing team, materially improve its productivity through the application of artificial intelligence and redesigned workflows, and lead the expansion of the Firm's service offering beyond non-disclosure agreements into additional categories of contract work. This is a mandate to build a business unit, supported by an established team, a proven revenue base, and direct engagement with the Firm's leadership.

Requirements

• A minimum of ten years' experience in legal practice, legal operations, or corporate and commercial legal services, with substantive depth in contract work.
• Direct experience with non-disclosure agreements and United States commercial contracts is strongly preferred, ideally within a private equity or financial services context.
• Availability to work in alignment with US Eastern business hours.
• A demonstrable record of building or transforming a function from a manual state into a structured, metrics-driven operation, with the ability to speak to the candidate's own contribution rather than that of a broader team.
• Genuine fluency in artificial intelligence. Candidates must be able to design and deploy AI-enabled workflows, not merely operate existing tools, and should expect this to be tested directly.
• Experience leading distributed teams, with a demonstrated commitment to structured people management and professional development.

Responsibilities

• Lead and develop a globally distributed team of approximately fourteen lawyers and paralegals.
• Establish structured people management practices, including regular one-to-ones, clear feedback, professional development, and strategic alignment across the function.
• Redesign the drafting and review workflow for non-disclosure agreements, embedding artificial intelligence so that the team's expertise is directed toward higher-value work and throughput is faster.
• Define the operating model and lead its implementation.
• Identify, scope, and launch additional contract review and drafting services capable of being delivered profitably at scale, growing the function from a single service line into a broader service offering.
• Assume ownership of turnaround times, quality standards, and client-facing outcomes for the function.
• Operate as a direct business partner to the Managing Partner, the Head of Firm Management, and revenue-generating partners of the Firm.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed