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Upwork

Sr Manager, Legal Operations

Toronto, ON, Canada

Pay: $135,500 - $169,500 CAD
Posting language: English
Posted: Sep 30, 2026

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Original job description

Upwork Inc.'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.

Since its founding, Upwork Inc. has facilitated more than $30 billion in total transactions and services as it fulfills its purpose to create opportunity in every era of work. Learn more about the Upwork Marketplace at Upwork.com and follow us on LinkedIn, Facebook, Instagram, TikTok, and X; and learn more about Lifted at Go-Lifted and follow on LinkedIn.

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 innovative 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.

Because you have a holistic view of how we operate, you are the culture carrier and the glue that holds our team together. You foster a collaborative environment where team members feel supported, valued, and connected.

Responsibilities:

Budget Management: Oversee the department budget by partnering with FP&A and Accounting on monthly accruals, forecasts, and annual planning. Identify vendor savings opportunities to self-fund incremental resources.
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.
Team Leadership & Culture: Promote team culture through events, recognition, and operating cadences that keep the Legal team connected and engaged. Plan and coordinate in-person team offsites. Manage agendas for team meetings.
Reporting & Analytics: Collect and analyze team metrics, compiling them into monthly and quarterly business reports. Prepare executive presentations, reports, and documentation.
Strategic Initiatives: Manage team-wide and cross-functional projects to support strategic initiatives, ensuring successful execution.

What it takes to catch our eye:

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
Experience using AI and automation tools to improve efficiency; experience with evaluating and implementing AI tools is a plus
Exceptional communication skills, organizational skills, and attention to detail
Ability to influence across all levels of the organization
Ability to scale operations as the department grows
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
A self-starter with the ability to work autonomously
Ability to build strong partnerships across Legal, and with cross-functional partners and outside counsel
Handle highly confidential and sensitive information with professionalism, discretion, and sound judgment
Comfortable learning new systems and tools quickly

Come change how the world works.

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.

Upwork is presently inviting candidates to apply for this existing vacancy. Applying to this posting allows you to express your interest in this current opportunity with Upwork. Qualified applicants may be contacted to review their resume in more detail.

We use BrightHire, an AI-enabled tool, to record interviews and summarize interview transcripts. The tool allows the interviewer to focus on the discussion and does not score or evaluate candidates or make recommendations. The interview transcripts are reviewed, and decisions are only made by humans. Candidates who prefer not to have their interview recorded through BrightHire can opt out when the interview is scheduled.

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).

The annual base salary range for this position is displayed below. The range displayed reflects the minimum and maximum salary for this position, and individual base pay will depend on your skills, qualifications, experience, and location. Additionally, this position is eligible for the annual bonus plan or sales incentive plan and eligibility to participate in our long term equity incentive program.

Annual Base Compensation

$135,500 - $169,500 CAD

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

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More about this job

Responsibilities

The Senior Manager of Legal Operations oversees department budgets, vendor billing, and technology implementation while driving process improvements. They also lead team culture initiatives, manage cross-functional projects, and provide analytical reporting to support strategic goals.

Requirements

Candidates must have 5+ years of experience in legal or business operations with a strong background in financial management and project execution. Proficiency in AI tools, exceptional communication skills, and the ability to scale operations in a fast-paced environment are essential.

Skills

Legal operations
Budget management
Vendor management
Technology implementation
Process improvement
Strategic project management
Financial acumen
AI tools
Automation
Communication skills
Organizational skills
Data analysis
Executive reporting
Stakeholder management
Change management

Benefits

Healthcare coverage
RRSP/DPSP retirement plans
Mental health support
Supplemental vacation
Employee stock purchase plan
Annual bonus plan
Long term equity incentive program

Visa sponsorship

Not detected in the job text

Keywords

Legal Operations
Budgeting
FP&A
Accounting
Vendor Management
AI Initiatives
Legal Tech Stack
Process Development
Operational Efficiency
Project Management
Strategic Planning
Data Analytics
Executive Presentations
Automation
Cross-functional Collaboration
Compliance
Reporting
Resource Management
Workflow Optimization
Stakeholder Engagement

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