Senior Functional Workday Analyst - Greater Toronto Area

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 ...

Job description

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

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; and learn more about Lifted at
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As a
Senior Functional Workday 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 of
  eligibility 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.

Upwork is establishing an operational hub in Toronto, Canada. The new office is expected to be fully operational by Q This role will require 3 days in office once we have an office open.

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.

Our partner will offer competitive benefits. When Upwork's hub is established, we will be excited to offer employment and benefits directly as business needs require.

Upwork is committed to building a diverse, inclusive, and equitable workforce. Employment decisions are made without regard to race, color, religion, gender, sexual orientation, gender identity, national origin, disability, or any other status protected by applicable law.