s (Nasdaq: UPWK) family of companies connects businesses with global, AI-enabled talent across every contingent work type including freelance, fractional, and payrolled. This portfolio includes the Upwork Marketplace, which connects businesses with on-demand access to highly skilled talent across the globe, and Lifted, which provides a purpose-built solution for enterprise organizations to source, contract, manage, and pay talent across the full spectrum of contingent work. From Fortune 100 enterprises to entrepreneurs, businesses rely on Upwork Inc. to find and hire expert talent, leverage AI-powered work solutions, and drive business transformation.

With access to professionals spanning more than 10,000 skills across AI & machine learning, software development, sales & marketing, customer support, finance & accounting, and more, the Upwork family of companies enables businesses of all sizes to scale, innovate, and transform their workforces for the age of AI and beyond. com and follow us on LinkedIn, Facebook, Instagram, TikTok, and X; You will be joining the award-winning Legal & Policy team. We support every business unit and function in the company to unlock opportunity and win with integrity. We enable, accelerate, and protect Upwork’s business in a collaborative and cutting-edge manner at a world-class level.

In this role, you serve as a strategic partner to the Chief Legal Officer and work closely with the entire Legal team, as well as cross-functional stakeholders, to ensure Legal programs run smoothly. You oversee all facets of the Legal team’s operations, play a key role in day-to-day support, and make an impact by driving efficiency, optimizing processes, scaling resources, and supporting strategic goals.

Budget Management: Oversee the department budget by partnering with FP&A; and Accounting on monthly accruals, forecasts, and annual planning.

Vendor Management: Oversee law firm and other vendor billing. Manage POs and invoices, and track vendor spend and alternative fee arrangements.

Technology Implementation:



Play a key role in driving AI initiatives and pushing adoption across the team. Evaluate and manage the Legal tech stack.

Process Development & Improvement: Identify resource gaps, streamline workflows, and drive operational efficiencies across the Legal team. Promote team culture through events, recognition, and operating cadences that keep the Legal team connected and engaged. Manage agendas for team meetings.

Collect and analyze team metrics, compiling them into monthly and quarterly business reports. Manage team-wide and cross-functional projects to support strategic initiatives, ensuring successful execution. You have 5+ years of experience in Legal operations, business operations, strategic project/program management, or related fields with progression into increasing responsibility and strategic scope, preferably with an in-house Legal team.

Strong financial acumen with experience managing a department budget Proven record of deploying systems end-to-end, and developing solutions to reduce routine escalations to senior team members Demonstrated success managing complex initiatives in a fast-paced environment Ability to build strong partnerships across Legal, and with cross-functional partners and outside counsel Upwork is establishing its first international operational hub in Toronto, Canada, and this role will require 3 days per week in office. We’re proud to offer benefits that go beyond the basics, including healthcare coverage for you and your family, RRSP/DPSP retirement plans, mental health support, wellness reimbursement program, supplemental vacation, and an Employee Stock Purchase Plan. Upwork is committed to building a diverse, inclusive, and equitable workforce.

Employment decisions are made without regard to race, color, religion, gender, sexual orientation, gender identity, national origin, disability, or any other status protected by applicable law. To learn more about how Upwork processes and protects your personal information as part of the application process, please review our Global Job Applicant Privacy Notice and the Applicant Privacy Addendum (Canada). #

📌 Sr Manager, Legal Operations (Toronto)
🏢 HR Tech Job
📍 Toronto