Senior People Operations Specialist

Location: Toronto, Ontario, Canada. The role will require 3 days in the office once the Toronto hub opens, with the office expected to be fully operational by Q4 2026.

Annual base compensation: $92,500–$133,000 CAD, plus eligibility for an annual bonus or sales incentive plan and long-term equity incentives.

Company

Upwork Inc. connects businesses with global, AI-enabled talent through its marketplace and enterprise workforce solutions.

What you will do

• Support onboarding, offboarding, organizational changes, and complex employee lifecycle matters.
• Coordinate employment-based immigration cases with external vendors and maintain related records, documentation, and workflows.
• Support employment eligibility and immigration compliance requirements.
• Guide managers and employees through performance management, coaching, documentation, and next steps.
• Partner with HRBPs, managers, People teams, and external vendors across a global footprint.
• Improve People Operations workflows, documentation, tools, and employee-facing resources using technology, automation, and AI.

Requirements

• 5+ years of progressive experience in People Operations, HR Generalist, shared services, or a related field.
• Hands-on experience supporting U.S. employment-based immigration, including common visa categories, immigration processes, and employment eligibility requirements.
• Strong understanding of employee lifecycle operations and HR practices.
• Experience partnering with HRBPs, managers, and cross-functional People teams.
• Strong judgment, discretion, problem-solving, prioritization, accuracy, and follow-through.
• Experience improving workflows, documentation, tools, or employee-facing resources.

Nice to have

• Experience supporting employees and People Operations processes across multiple countries or regions.
• Exposure to immigration or employment processes in additional countries.
• Experience with performance management, manager coaching, or employee relations.

Culture & Benefits

• The role initially operates through a hiring partner while the Toronto hub is being established.
• The partner provides benefits during the initial employment period.
• There may be an opportunity to transition to direct Upwork employment and benefits after the hub is established, depending on business needs and other requirements.
• Interview recording through BrightHire is optional for candidates.