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About the Role

Caseware is seeking a Legal Operations Manager to scale its in-house legal function. This role will serve as the operational backbone of the department, bringing structure, efficiency, and scalable processes to a fast-paced SaaS company. The position offers the opportunity to shape legal operations from an early stage with direct exposure to senior leadership.

Responsibilities

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.
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.

Requirements

Bachelor’s degree in business, legal studies, or a related field; a paralegal diploma or equivalent experience is an asset.
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.

Skills

Legal technology
AI
Contract lifecycle management (CLM)
E-signature tools
Matter management systems
Process design
Outside counsel management
Vendor management
Budget management
Project management
Data analytics
BI tools (Power BI, Tableau)

Location

Toronto, ON

Work Type

Hybrid
Full-time
Permanent

Experience Level

3-7 years

Education Level

Bachelor's degree in business, legal studies, or a related field
Paralegal diploma or equivalent experience

Salary/Compensations

$100,000 CAD - $120,000 CAD per year

Benefits

Discretionary bonus
Commission
Health insurance
Retirement plans
Flexible work options
Generous time-off policies

About the Company

Caseware is a Canadian Fintech company with over 30 years of leadership in the global audit and accounting software industry.
The company has over 500,000 users across 130 countries and offers products in 16 languages.
Caseware's cutting-edge software products are designed for accounting firms, corporations, and governments.
With a recent strategic investment from Hg Capital in 2020, Caseware is in its next major growth phase.
Caseware is committed to a collaborative culture, where ideas are valued and knowledge sharing is encouraged.

Equal Opportunity

Caseware is dedicated to building teams as diverse as its customers in an equitable and inclusive way.
We welcome and encourage candidates of all backgrounds to apply.
Should you require accommodations or have any questions at any point during the application or interview process, please e-mail our People Operations team at talent@caseware.com.