Legal Operations Manager

Caseware combines over 35 years of industry expertise with AI-powered technology to transform how audit and accounting professionals work. Serving organizations across 130 countries, we bring intelligent automation directly into audit and financial reporting workflows—helping professionals reduce manual work, navigate complexity, and focus on informed decisions. Join our global team and help build technology that strengthens trust in financial information.

Caseware is looking for a Legal Operations Manager to help scale our in-house legal function.

This is a unique opportunity for an operationally minded individual to join a 4-lawyer in-house team supporting a global company. Reporting directly to the General Counsel, you will be the operational backbone of the department, bringing structure, efficiency, and scalable processes to how the team works at a fast-paced SaaS company. You will own the systems, processes, vendor relationships, and metrics that allow the lawyers to focus on legal judgment.

You will have a wide range of responsibilities, with a focus on legal technology and systems, process design, and outside counsel and vendor management. As the first dedicated Legal Operations hire at Caseware, you will have the opportunity to shape and own legal operations processes from an early stage, with direct exposure and access to the General Counsel and senior leadership. This is a hands-on, generalist role suited to someone with strong technology and AI skills who is motivated to help others succeed.

❗This is an existing vacancy.

❗This is a full-time, permanent position.

📍This is a hybrid role, requiring the successful candidate to work three days a week at our Toronto office (351 King St E, Toronto, ON).

What you will be doing

• Administer and continuously improve the contract lifecycle management (CLM) platform, e-signature tools and matter management systems, driving adoption across the business.
• Design, document, and maintain repeatable workflows for contract intake, review routing, approvals, and escalations so the legal team can scale with the business.
• Manage relationships and budgets with outside counsel and legal vendors, including negotiating rates, tracking spend against budget, and reviewing invoices.
• Maintain the legal department budget, prepare spend and matter-volume reports, and build dashboards and metrics that demonstrate the legal team’s impact to the business.
• Support the end-to-end contract process, including templates, playbooks, clause libraries, and self-serve tools for the Sales and Procurement teams.
• Maintain corporate records for all legal entities, handle all statutory and annual filings, ensure corporate compliance in all jurisdictions, and respond to UBO and KYC requests independently.
• Design and maintain the department’s internal knowledge base, training materials, and onboarding resources for new hires and business stakeholders.
• Identify gaps and design process improvements, and where appropriate, take the lead in legal technology implementations and use of AI to achieve objectives.
• Keep legal documents and records accurate, organized, and easy to access; provide support to lawyers and other stakeholders.

What you will bring

• Bachelor’s degree in business, legal studies, or a related field; a paralegal diploma or equivalent experience is an asset. A law degree is not required for this role.
• 3–7 years of experience in legal operations, paralegal work, or a similar operational role; an in-house legal team or law firm operations background is strongly preferred.
• Hands-on experience implementing and using CLM and e-signature tools and other legal technology, including AI.
• Strong project management skills, with the ability to independently prioritize across multiple concurrent initiatives in a lean team.
• Experience managing budgets, vendor relationships, and outside counsel spend and invoicing.
• Excellent written and verbal communication skills, with the ability to work directly with lawyers and business stakeholders at all levels.
• A high degree of discretion and judgment when handling confidential and sensitive information.
• Experience building a legal operations function from the ground up in a small legal department is an asset.
• Exposure to data analytics or BI tools (e.g., Power BI, Tableau) for legal reporting is an asset.
• Strong AI aptitude, with experience applying AI tools to drive operational efficiency and process improvement.

Salary Range:

The annual base salary for this position is between $100,000 CAD and $120,000 CAD per year.

This role is also eligible for discretionary bonus and/or commission, as well as other benefits. Actual pay within the listed range will be determined based on factors such as transferable skills, relevant experience, market conditions, and primary work location. The posted range is subject to change and may be updated periodically.

What's in it for you:

Shape what’s next with AI: Help transform audit and accounting through AI-powered technology. Explore new ways to bring AI into our own workflows, rethink how work gets done, and turn ideas into meaningful improvements for our teams and customers.

Make an impact that matters: Contribute to solutions that help professionals navigate complexity, make informed decisions, and strengthen trust in financial information around the world.

Bring your voice. Expand your perspective: Collaborate with a diverse global team where your ideas are valued, knowledge is shared, and different perspectives lead to better outcomes.

Build a career that grows with you: Develop your skills, take on new challenges, and explore career opportunities as our business and technology evolve.

Thrive at work and beyond: Enjoy competitive compensation, comprehensive benefits, recognition programs, and performance bonuses, alongside flexible work options, remote opportunities, and generous time off.

Many Voices, One Team:

We’re committed to building teams as diverse as our customers through equitable and inclusive hiring. We welcome candidates of all backgrounds. If you need accommodations or have questions at any stage of the application or interview process, contact our People Operations team at [email protected].

Background Check:

All successful candidates will undergo background screening, which may include identity verification, criminal record checks, and/or reference checks, as appropriate to the role and location and in accordance with applicable law.

Security and Fraud:

All employees are expected to apply security best practices and work within secure handling guidelines to perform assigned responsibilities when accessing data and business information.

Caseware takes the security of candidates seriously. All legitimate communication from us will come from email addresses ending in @caseware.com and our open positions are always listed on reputable job boards and on our website https://jobs.lever.co/caseware. We will NEVER ask for payment or financial information from you. If you receive an unsolicited job offer, proceed with extreme caution.