Clio is the global leader in legal AI technology, empowering legal professionals and law firms of every size to work smarter, faster, and more securely.

We are currently seeking a Senior Global Benefits & Leaves Specialist to join our Total Rewards team If you are passionate about building people-centric leave programs that empower Clions to take the time they need in order to do their best work, this is the role for you. We are looking for someone who thrives in a builder environment, where you can shape infrastructure from the ground up.

Reporting to the Senior Manager, Global Benefits, you will lead the design of our global leave philosophy and build and implement leave programs across approximately ten+ countries, ensuring seamless integration with Workday and payroll. With a high degree of autonomy, you will translate regulatory complexity and organizational values into programs Clions can actually use.

What Your Team Does

The Total Rewards team is responsible for designing and building the competitive, scalable reward programs that enable Clio’s human and high-performing culture. As part of the Total Rewards team, the benefits team’s goal is to standardize and enhance our global programs, ensuring our benefits are scalable and impactful. Through close partnerships across the business and deep market insights, we translate global strategy into meaningful benefit experiences that support Clio’s long-term goals and help our people thrive.

What You’ll Work On

Global Leave Philosophy

Design and document a globally consistent leave philosophy aligned with Clio’s values and total rewards strategy

Present the philosophy framework to senior leadership for approval and align stakeholders on implementation approach





Define guiding principles for equity, compliance, and employee experience across geographies

Benchmark leave programs against market comparators across all operating countries

Program Design & Implementation

Benchmark leave entitlements and program design against market comparators across 10+ countries, ensuring Clio's programs are competitive and aligned with local norms

Design, build, or restructure the following leave types across all operating countries, ensuring compliance with local laws and regulatory requirements:

Short-Term Disability (STD) and Long-Term Disability (LTD)

Parental leave, maternity/paternity leave, and adoption leave

Flexible and unlimited vacation policies

Sick leave and medical accommodation programs

Bereavement, jury duty, and other statutory leave obligations

Partner with Legal, People Business Partners, and Payroll to validate compliance across jurisdictions including Canada, US, UK, Ireland, Australia, Spain, and LATAM

Manage vendor and insurer relationships relevant to leave and disability programs

Systems Integration & Operations

Partner with the HRIS team to integrate leave programs with Workday and payroll, ensuring accurate leave tracking, accruals, and reporting

Develop employee-facing resources, manager toolkits, and leave intake processes





Train People Business Partners and managers on leave administration across regions

Build audit and compliance monitoring mechanisms to ensure programs remain current with legislative changes

Act as the senior escalation point for complex leave and accommodation cases, providing a high-touch experience for Clions

This is a builder role. You will be creating infrastructure where little or none currently exists. The right candidate thrives on ownership, moves comfortably in ambiguity, and can operate from a high-level vision through to operational detail.

What You May Have

5+ years of directly relevant experience in global leaves, absence management, or disability programs, ideally with exposure to North America, Europe, and LATAM

Deep knowledge of leave-related regulatory requirements across multiple jurisdictions, including US and Canada

Proven ability to plan, lead, and own major projects end to end with minimal oversight, building clarity and structure from a high-level vision

Experience designing or significantly restructuring leave programs, not just administering existing ones

Excellent stakeholder management and communication skills, with demonstrated ability to influence across functions and seniority levels

CEBS, GBA, or equivalent designation is considered an asset

Experience in a fast-paced tech or high-growth environment; comfort operating in a builder environment with ambiguity and constant change

This is a current role.

What you will find here:

Compensation is one of the main components of Clio’s Total Rewards Program. We have developed a series of programs and processes to ensure we are creating fair and competitive pay practices that form the foundation of our human and hig

📌 Senior Global Benefits (Toronto)
🏢 Clio
📍 Toronto