Sr Manager, Legal Operations

Upwork; Toronto; On-site; CAD 120,000 - 180,000; Full time

Benefits offered by this job

Healthcare coverage for you and your f

RRSP/DPSP retirement plans

Mental health support

Wellness reimbursement program

Supplemental vacation

Employee Stock Purchase Plan

Job summary

Upwork Inc. in Toronto is seeking a Senior Leader for Legal Operations to partner with the Chief Legal Officer and manage day-to-day operations across the Legal team.

You will drive efficiency, scale resources, and support strategic goals while maintaining strict confidentiality. You will oversee budgeting, vendor management, AI-enabled initiatives, and cross-functional collaboration with partners and outside counsel to deliver programs that align with Upwork’s business priorities.

Qualifications

• 5+ years in Legal operations or related fields with progression into strategic scope
• Strong financial acumen with experience managing a department budget
• Experience using AI and automation tools to improve efficiency; evaluating and implementing AI tools is a plus
• Exceptional communication and organizational skills, with attention to detail
• Ability to influence across all levels of the organization and scale operations

Responsibilities

• Oversee the Legal team's operations and budgets with FP&A and Accounting
• Manage law firm/vendor billing, POs, invoices, and spend
• Drive AI initiatives and adopt the Legal tech stack across the team
• Identify resource gaps, streamline workflows, and improve processes
• Lead team events, run in-person offsites, and manage team meetings
• Prepare monthly/quarterly reports and executive presentations
• Manage cross-functional projects to support strategic initiatives

Skills

Legal operations

Budget management

AI tools

Communication

Collaboration

Education

Bachelor's degree in a relevant field

Tools

BrightHire

AI software

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.

Benefits:

• healthcare coverage for you and your family
• RRSP/DPSP retirement plans
• mental health support
• wellness reimbursement program
• supplemental vacation
• 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.

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.

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