Senior People Operations Specialist

About the Position

As a Senior People Operations Specialist at Upwork Inc., you will play a key role in delivering thoughtful, scalable people programs and operational support across the employee lifecycle. This role is ideal for someone who brings strong operational instincts, thrives in complexity, and enjoys moving between detailed execution, problem-solving, process improvement, and partnership.

Responsibilities

• Partner on onboarding, offboarding, organizational changes, and other employee lifecycle moments, providing guidance to employees, managers, and HRBPs on more complex People Operations matters.
• Own end-to-end coordination of immigration matters alongside our external vendor, serving as a trusted internal resource for employees and managers navigating immigration processes and requirements.
• Maintain accurate immigration records, documentation, communications, and workflows while supporting employment eligibility and related compliance requirements.
• Navigate ambiguous or sensitive situations with discretion, sound judgment, and an understanding of when to independently resolve an issue versus engage the appropriate partner.
• Provide guidance and operational support across coaching and performance processes, helping managers navigate tools, documentation, expectations, and next steps. Act as a trusted partner for employees and managers, balancing advocacy for people with business needs.
• Support People Operations processes across our growing global footprint, partnering with internal teams and external vendors to address local requirements and maintain consistent employee support.
• Identify opportunities to simplify and improve People processes, using technology, automation, and AI where they can meaningfully reduce manual work or improve the employee and manager experience.

Requirements

• 5+ years of progressive experience across People Operations, HR Generalist, shared services, or related roles, ideally in a fast-moving or evolving organization. Experience supporting employees and People Operations processes across multiple countries or regions is a plus.
• Hands-on experience supporting U.S. employment-based immigration, with working knowledge of common visa categories, immigration processes, and employment eligibility requirements. Exposure to immigration or employment processes in additional countries is a plus.
• Strong understanding of employee lifecycle operations and HR practices, with experience owning processes from intake through resolution.
• Experience partnering with HRBPs, managers, and cross-functional People teams to solve employee and operational challenges.
• Experience with performance management, manager coaching, or employee relations is valuable; demonstrated ability to quickly develop expertise in new areas is equally important.
• Strong judgment and problem-solving skills, with the ability to navigate ambiguity and determine when an issue requires escalation or additional partnership.
• Process-oriented mindset with demonstrated experience improving workflows, documentation, tools, or employee-facing resources.
• Ability to independently manage multiple priorities while maintaining a high degree of accuracy, responsiveness, and follow-through.

We Offer

• Competitive salary range: $92,500 - $133,000 CAD
• Comprehensive healthcare coverage for you and your family
• RRSP/DPSP retirement plans
• Mental health support
• Wellness reimbursement program
• Supplemental vacation
• Employee Stock Purchase Plan

About the Company

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.

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.

Application Process

To apply for this position, please submit your resume/CV through the application portal. We use BrightHire, an AI-enabled tool, to record interviews and summarize interview transcripts. The tool allows the interviewer to focus on the discussion and does not score or evaluate candidates or make recommendations. The interview transcripts are reviewed, and decisions are only made by humans. Candidates who prefer not to have their interview recorded through BrightHire can opt out when the interview is scheduled.

For more information on how Upwork processes and protects your personal information as part of the application process, please review our Global Job Applicant Privacy Notice and the Applicant Privacy Addendum (Canada).

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