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Head of Legal Outsourcing Services

Sterlington


Job Location:

Toronto - Canada

Monthly Salary: Not provided by the employer
Posted: 16 July 2026 (30+ days ago)
Application Deadline: 13 October 2026
Vacancies: 1 Vacancy

Job Summary

Reports to: Head of Corporate/M&APractice
Department:Outsourcing
Contract: Independent Contract
Location:100% Remote
Working Hours:Eastern Standard Time (EST)

Our Firm:

Sterlington PLLC is a full-service law firm focusing on complex corporate litigation executive compensation and private wealth matters. As a firm we focus on theeconomicas well as the legal aspects of our matters. Among other strengths Sterlington is the ultimate law firm for founders senior executives and UHNWIs as well as their related businesses. Learn more at:

The Opportunity

The Firmoperatesa globally distributed outsourcing function of approximately fourteen professionals most of whom are qualified lawyers with LLM credentials in their respectivejurisdictions. This team drafts and reviews non-disclosure agreements at scale in support of the Firms 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 Firms service offering beyond non-disclosure agreements intoadditionalcategories 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 Firms leadership.

What Youll Do:

  • Team leadership.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.
  • AI-driven transformation. Redesign the drafting and review workflow for non-disclosure agreements embedding artificial intelligence so that the teamsexpertiseis directed toward higher-value workand throughputisfaster. Define the operating model andleadits implementation.
  • Business expansion. Identify scopeand launchadditionalcontract review and drafting services capable of being delivered profitably at scale growing the function from a single service line into a broader service offering.
  • Service delivery. Assume ownership of turnaround times quality standards and client-facing outcomes for the function.
  • Stakeholder partnership. Operate as a direct business partner to the Managing Partner the Head of Firm Management and revenue-generating partners of the Firm.

What Were Looking For:

  • 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 candidates own contribution rather than that of a broader team.
  • Genuine fluency in artificial intelligence. Consistent with the Firms standard for all hires 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.

At Sterlington we believe that world-class talent has no boundaries. We are committed to fostering a diverse and inclusive environment where unique perspectives arevaluedand every individualhas the opportunity tothrive. We encourage all qualified candidates to apply.


Required Experience:

Director


About Company

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Sterlington is an international virtual law firm with leading capabilities in sophisticated transactional and litigation work and legal contract outsourcing.

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