Sign up to access all features of our service.
  • Job search
  • Favorites
  • Create a CV
    New
  • Salaries
  • Subscriptions

Head of Legal Outsourcing Services

Sterlington, PLLC

Reports to:  Head of Corporate/M&A Practice
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 the economic as 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 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.  

What You'll 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 team's expertise is directed toward higher-value work and throughput is faster. Define the operating model and lead its implementation .
  • Business expansion. 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.
  • 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 We're 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 candidate's own contribution rather than that of a broader team.
  • Genuine fluency in artificial intelligence. Consistent with the Firm's 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 are valued and every individual has the opportunity to thrive. We encourage all qualified candidates to apply.  

 

Vacancy posted 17 hours ago
Similar jobs that could be interesting for youBased on the Head of Legal Outsourcing Services in Toronto, ON vacancy
  • $48k - $60k per year

     ...Pension Outsourcing - Customer Service Representative (Remote) ~202604434 ~Montreal, Quebec, Canada ~Toronto, Ontario, Canada ~Full time View favourites Description WTW benefit consultants have deep experience working with organizations of all types and sizes... 
    Outsource
    Outsourcing
    Full time
    Temporary work
    Work at office
    Remote work
    Worldwide

    WTW

    Toronto, ON
    6 hours ago
  • $65k - $85k per year

     ...Senior Analyst - Pension Outsourcing ~202604433 ~Montreal, Quebec, Canada ~Toronto, Ontario, Canada ~Full time View favourites...  ...wide variety of recurring defined benefit plan administration services for clients, contribute to special projects, and provide ad hoc... 
    Outsource
    Outsourcing
    Full time
    Temporary work
    Work at office
    Worldwide
    3 days per week

    WTW

    Toronto, ON
    6 hours ago
  • $90k - $125k per year

     ...Director - Pension Outsourcing ~202604428 ~Montreal, Quebec, Canada ~Toronto, Ontario, Canada ~Full time View favourites...  ...wide variety of recurring defined benefit plan administration services for clients, contribute to special projects, and provide ad hoc... 
    Outsource
    Outsourcing
    Full time
    Temporary work
    Work at office
    Worldwide
    3 days per week

    WTW

    Toronto, ON
    2 days ago
  •  ...The Centre for Addiction and Mental Health (CAMH) is seeking an in-house full-time permanent Security Guard 2 to work in the Security Services department. This is an exciting and valuable opportunity for anyone embarking on a law enforcement career. CAMH Security Services... 
    Suggested
    Permanent employment
    Full time
    Work at office
    Shift work
    Night shift
    Weekend work
    Afternoon shift

    CAMH

    Toronto, ON
    9 days ago
  • $75k per year

     ...Head Chef Escape Manor Toronto 383 King Street West, Toronto, ON Full-Time | Salary: $75,000 per year Lead the Kitchen. Inspire...  ...Ensuring the kitchen is organized, prepared, and ready for service every day What We're Looking For The ideal candidate will have... 
    Suggested
    Full time
    Weekend work
    Afternoon shift

    Escape Manor

    Toronto, ON
    12 days ago
  • $200k - $300k per year

     ...the same. We’re looking for a Founding Head of Enterprise Sales to own sales execution...  ...buying decisions often involve procurement, legal, design leaders, and multiple internal...  ...Experience working with SDRs, contractors, or outsourced lead qualification support. At the time... 
    Outsource
    Outsourcing
    Long term contract
    Full time
    Contract work
    For contractors
    Internship
    Immediate start
    Remote work
    Home office

    Creative Market

    Toronto, ON
    22 days ago
  • $175k - $200k per year

     ...America, the UK, EU, and APAC. Director, Legal Affairs & Operations Banyan Software  |...  ...Toronto, ON (Hybrid - 3 days onsite)  |  Head Office Legal Team This is not a typical...  ...You'll Do Portfolio Company Shared Services Lead post-close legal onboarding for newly... 
    Permanent employment
    Contract work
    Work at office
    Worldwide
    3 days per week

    Banyan Software

    Toronto, ON
    11 days ago
  •  ...Reference no. R2862708  Position title: Head of Data Governance Products Location:...  ...stakeholders (including, but not limited to, legal, privacy, cybersecurity, compliance and...  ...information to identify patterns, improve services, or support decision-making. The Company... 
    Full time
    Work at office
    Work from home
    3 days per week

    Sanofi

    Toronto, ON
    6 days ago
  •  ...Toronto, Ontario, Canada Hours: 37.5 Line of Business: Legal Pay Details: We're committed to providing fair and equitable...  ...Global Anti-Money Laundering and Enterprise Technology & Shared Services. Our dynamic professionals ensure compliance with the legal requirements... 
    Full time
    Work at office
    Immediate start
    Work from home
    Flexible hours

    TD Bank

    Toronto, ON
    5 days ago
  •  ...website. About TMF Group TMF Group is a leading provider of critical administrative services, helping clients invest and operate safely around the world. We provide legal, financial and employee administration through TMF Group’s teams in 120 offices. Discover the... 
    Full time
    Work at office
    2 days per week

    TMF Group

    Toronto, ON
    16 hours ago
  • About NationGraph NationGraph is making public sector data accessible and actionable for businesses selling to cities, counties, state agencies, schools, and special districts. NationGraph’s data and intelligence engine provides buying signals derived from millions ...
    Long term contract
    Full time
    Internship
    Immediate start
    Work from home
    Flexible hours

    NationGraph

    Toronto, ON
    16 hours ago
  • $150k - $180k per year

     ...The Head of Controlling is responsible for overseeing financial planning, analysis, accounting, and reporting for the Canadian business. This role serves as a key strategic finance partner to Red Bull Canada's Leadership Team (LT) and acts as the finance lead for major... 
    Full time
    Work at office

    Red Bull

    Toronto, ON
    1 day ago
  • $150k - $180k per year

     ...collaboration, innovation, and impact across everything we do. About our Legal Craft Our Legal Craft partners across Klick to enable business...  ...Experience providing employment law counsel in a professional services, agency, healthcare, or life sciences environment Familiarity... 
    Long term contract
    Full time
    Contract work

    Klick Non-billable

    Toronto, ON
    1 day ago
  •  ...Job Responsibility: Head Coach, Competitive Program Canada First Academy for Soccer Excellence - Toronto, ON About us Canada First Academy for Soccer ExcellenceCanada First Academy (CFA) is a Toronto-based soccer academy for recreational and elite player training... 
    Hourly pay
    Long term contract
    Part time
    Live In
    Work at office
    Local area
    Monday to friday
    Weekend work
    Afternoon shift

    Canada First Academy for Soccer Excellence

    Toronto, ON
    5 days ago
  •  ...About Us Legora is redefining how legal work gets done. Not built for lawyers, built with them. We work alongside the world’s best legal teams, who expect excellence, precision, and speed, and we hold ourselves to the same bar. Our AI-native workspace lets legal professionals... 
    Full time
    Internship
    Work at office
    Shift work

    legora

    Toronto, ON
    16 hours ago
  • $59.3k - $72.5k per year

    We are looking for a highly organized and proactive Legal Claims Assistant to join one of our top clients in the Insurance industry! In...  ...Excellent communication, listening, interpersonal, and customer service skills. Exceptional attention to detail and proofreading abilities... 
    Work at office
    Local area
    Flexible hours

    Randstad

    Toronto, ON
    12 days ago
  • $58k - $72k per year

     ...Tétrault is a leading Canadian law firm offering a full suite of legal and business solutions to clients in Canada and around the world....  ...groups as required in order to maintain the Firm’s legal support services ensuring continuous legal operations and client satisfaction.... 
    Full time
    Work at office

    McCarthy Tétrault

    Toronto, ON
    7 days ago
  • $105k - $125k per year

     ...millions of players over their lifetime. These are enduring live-service virtual worlds with rich in-game economies, virtual goods,...  ...operations teams. Experience managing vendor transitions or bringing outsourced services in-house. Experience with hardware inventory, device... 
    Outsource
    Outsourcing
    Long term contract
    Full time
    Work at office
    Remote work
    3 days per week

    Big Viking Games

    Toronto, ON
    7 days ago
  •  ...insatiable appetite for building what no one has built before.  This is a hybrid role with 1 day in the office.  About the Role The Head of Finance reports to the Chief Operating Officer and leads the finance function for a global business generating over $50M in revenue,... 
    Long term contract
    Work at office
    Immediate start
    1 day per week

    Behavox

    Toronto, ON
    7 days ago
  • $75k per year

    Overview Languages English Education ~ Secondary (high) school graduation certificate Experience 3 years to less than 5 years On site Work must be completed at the physical location. There is no option to work remotely. Benefits Health benefits...
    Permanent employment
    Full time
    Remote work

    Escape Manor Toronto

    Toronto, ON
    6 days ago
  • $36.5 per hour

     ...completed at the physical location. There is no option to work remotely. Work setting ~ Restaurant Ranks of chefs Sushi chef Head chef Fish chef Responsibilities Tasks Estimate amount and costs of supplies and food items Estimate labour costs... 
    Permanent employment
    Full time
    Remote work

    MSSM

    Toronto, ON
    9 days ago
  • Job Responsibility: The ideal candidate is serve as the lead marketing executive. You will manage all marketing efforts including planning, research, advertising, communications and public relations in line with our objectives. Previous 'brand refresh' experience would be ...
    Full time

    WDI Group

    Toronto, ON
    9 days ago
  •  ...respected organization within the insurance and financial services sector is seeking a Legal Executive Assistant to join its Legal & Compliance team in...  ...to the Legal & Compliance team. Reporting directly to the Head of Legal, you will play a critical role in ensuring regulatory... 
    Hourly pay
    Contract work
    Work at office

    Hays

    Toronto, ON
    22 days ago
  •  ...About the role: We are seeking an experienced and entrepreneurial Head of Consumer Financing to lead and scale Clutch’s consumer...  ...scale lending operations, including loan origination, underwriting, servicing, and collections processes. Identify opportunities to automate and... 
    Remote work

    Clutch Technologies Inc.

    Toronto, ON
    12 days ago
  • $75k per year

     ...Responsibilities Tasks Schedule and confirm appointments Maintain filing system Prepare and key in correspondence and legal documents Experience and specialization Computer and technology knowledge PCLaw in the Cloud Dictaphone MS Word MS Outlook... 
    Permanent employment
    Full time
    Remote work

    The Hiring Partner Inc

    Toronto, ON
    8 days ago
  •  ...Driving the Future of Connected Transportation Empowering Businesses with Data-Driven Fleet Intelligence Geotab is seeking a Legal Counsel to manage complex legal agreements and negotiations across technology, data licensing, government contracting, privacy, and intellectual... 
    Full time

    jobs-page-4dc2685b-eb82-46d1-a3f9-1f0764dba814

    Toronto, ON
    16 hours ago
  •  ...About Us Legora is redefining how legal work gets done. Not built for lawyers, built with them. We work alongside the world’s best legal teams, who expect excellence, precision, and speed, and we hold ourselves to the same bar. Our AI-native workspace lets legal professionals... 
    Full time
    Work at office

    legora

    Toronto, ON
    16 hours ago
  • Tali AI is on a mission to build industry-leading products that solve real-world problems for clinicians today.   How do we do this? Our AI-powered medical assistant empowers clinicians by removing the administrative burden that pulls them away from patients. When clinicians...

    11855760-canada-inc

    Toronto, ON
    20 days ago
  • $215.6k per year

     ...RBH website: [ #RBH **Key things to know before you apply:** Be legally permitted to work in Canada. **FAITES PARTIE D'UN CHANGEMENT RÉVOLUTIONNAIRE...  ...: [ #RBH **Éléments clés à savoir avant de postuler :** Être légalement autorisé à travailler au Canada. -- [#J-MCITY] [#J-ENTERPRISE... 
    Daily paid
    Full time
    Flexible hours

    Philip Morris International

    Toronto, ON
    7 days ago
  • $130k - $180k per year

     ...will find a strong sense of belonging at Quince. THE ROLE Head of Merchandising, CPG Canada We are seeking a Head of Merchandising...  ...Google Meets or Zoom—never via messaging apps or other calling services. Offers are merit-based, communicated verbally, and followed up... 
    Long term contract
    Work at office
    Local area

    Quince

    Toronto, ON
    8 days ago

Do you want to receive more vacancies?

Subscribe and receive similar vacancies to Head of Legal Outsourcing Services. Be the first to apply!