Senior Workday Analyst Job Toronto area,Ontario Canada,HR/Recruitment

Upwork Inc.’s (Nasdaq: UPWK) family of companies connects businesses with global, AI-enabled talent across every contingent work type including freelance, fractional, and payrolled. This portfolio includes the Upwork Marketplace, which connects businesses with on-demand access to highly skilled talent across the globe, and Lifted, which provides a purpose-built solution for enterprise organizations to source, contract, manage, and pay talent across the full spectrum of contingent work.

From Fortune 100 enterprises to entrepreneurs, businesses rely on Upwork Inc. to find and hire expert talent, leverage AI-powered work solutions, and drive business transformation. With access to professionals spanning more than 10,000 skills across AI & machine learning, software development, sales & marketing, customer support, finance & accounting, and more, the Upwork family of companies enables businesses of all sizes to scale, innovate, and transform their workforces for the age of AI and beyond.

Since its founding, Upwork Inc. has facilitated more than $30 billion in total transactions and services as it fulfills its purpose to create opportunity in every era of work. Learn more about the Upwork Marketplace at and follow us on,,,, and; and learn more about Lifted at and follow on.

As a Senior HR Systems Analyst, you’ll lead the configuration, optimization, and continuous improvement of Upwork’s Workday Benefits, Absence, and Time Tracking modules while contributing to the broader HR technology strategy. You’ll collaborate globally across People, IT, and Finance teams to design scalable, data-driven solutions that enhance employee experience, streamline processes, and strengthen data integrity. This is a hands-on role where your Workday expertise will directly shape how our people programs operate and evolve worldwide.

Responsibilities

Serve as the primary configuration lead for Workday Benefits, Absence, and Time Tracking modules, including eligibility rules, accruals, enrollment events, and business processes.

Design, test, and implement scalable solutions that align with global compliance and improve employee experience and operational efficiency.

Partner with Total Rewards, People Operations, and IT to develop automated workflows and ensure seamless integration across systems.

Develop and maintain Workday reports, dashboards, and calculated fields that deliver actionable insights and support compliance across regions.

Lead Workday release management activities—evaluating new features, assessing global impact, and recommending adoption strategies.

Troubleshoot and resolve complex configuration and integration issues while maintaining data accuracy and system reliability.

Mentor and coach team members on Workday best practices, configuration standards, and testing methodologies.

What it takes to catch our eye

Proven, hands-on experience configuring and administering Workday Benefits, Absence, and Time Tracking modules (Core HCM and Performance experience strongly preferred).

Demonstrated success leading HR Tech projects from design through testing and deployment.

Deep understanding ofeligibility rules, accrual logic, business processes, and compliance frameworks within Workday.

Strong reporting and analytical skills with experience building custom reports and dashboards.

Clear, collaborative communicator who partners effectively with global teams across time zones and cultures.

Curiosity and a continuous improvement mindset—committed to learning, sharing, and evolving processes for scale.

Come change how the world works.

This position will initially be employed through a partner to ensure a seamless hiring process while we establish the hub. Once the hub is established, there may be opportunities to transition to employment with Upwork depending on business needs and other requirements. While employed by the partner, you’ll work as part of Upwork’s team, with access to our resources, culture, and growth opportunities.

Upwork is an Equal Opportunity Employer committed to recruiting and retaining a diverse and inclusive workforce. We do not discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, or other legally protected characteristics under federal, state, or local law.

Please note that a criminal background check may be required once a conditional job offer is made. Qualified applicants with arrest or conviction records will be considered in accordance with applicable law, including the California Fair Chance Act and local Fair Chance ordinances. The Company is committed to conducting an individualized assessment and giving all individuals a fair opportunity to provide relevant information or context before making any final employment decision.


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