Role overview

Caseware is seeking a Legal Operations Manager to build and lead operational functions within its in-house legal department. The company combines decades of industry expertise with AI-powered technology to serve audit and accounting professionals across 130 countries. As the first dedicated Legal Operations hire, you will work directly with the General Counsel to establish scalable processes and systems that enable a four-lawyer legal team to function efficiently at a growing SaaS organization.

Key responsibilities

Establish and manage legal technology platforms and systems that support the department’s workflow and decision-making.
Design and implement operational processes that create structure and efficiency across the legal function.
Oversee relationships with outside counsel and external vendors, including performance management and optimization.
Develop and track metrics and key performance indicators that measure the effectiveness of legal operations.
Serve as the operational backbone of the department, enabling lawyers to focus on substantive legal work and strategic decisions.
Work hands-on across a broad range of operational challenges in a generalist capacity.

Requirements

Strong background in legal operations, legal technology, or legal department management.
Demonstrated proficiency with legal technology platforms and systems.
Experience designing and implementing scalable business processes.
Proven ability to manage vendor and outside counsel relationships effectively.
Strong technology skills and familiarity with AI tools and applications.
Ability to work independently and take ownership of projects from inception to completion.

What makes this role worth considering

This position offers rare ground-floor opportunity to shape legal operations at an established global company during a growth phase. You will have direct access to and reporting relationship with the General Counsel and senior leadership, providing meaningful visibility and influence across the organization. The hybrid arrangement requires three days per week at the Toronto office, allowing for focused collaboration while maintaining flexibility.