Legal Operations Manager

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.