Senior People Operations Specialist

Upwork; Toronto; Hybrid; CAD 90,000 - 130,000; Full time

Benefits offered by this job

Competitive benefits

Hybrid work model

Job summary

Upwork is establishing an operational hub in Toronto, Canada. We seek a Senior People Operations Specialist to deliver scalable programs across the employee lifecycle, with a focus on immigration, global mobility, performance management, and HRBP enablement.

The role partners with HRBPs, managers, and vendors across multiple regions. You will own end-to-end immigration coordination, maintain records, and help drive process improvements while supporting a growing global footprint.

Qualifications

• 5+ years of progressive experience across People Operations, HR Generalist, shared services, or related roles.
• 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 knowledge of visa categories and employment eligibility requirements.

Responsibilities

• Partner on onboarding, offboarding, organizational changes, and other lifecycle moments, guiding employees, managers, and HRBPs on complex People Operations matters.
• Own end-to-end coordination of immigration matters with external vendors, serving as a trusted internal resource for employees and managers.
• Maintain immigration records, documentation, communications, and workflows, supporting eligibility and compliance.
• Navigate ambiguous or sensitive situations with discretion and sound judgment.
• Provide guidance across coaching and performance processes, helping managers and employees with tools, documentation, expectations, and next steps.
• Support People Operations processes across our global footprint, collaborating with internal teams and vendors to meet local requirements.
• Identify opportunities to simplify and improve People processes using technology, automation, and AI.

Skills

People Operations

HR Generalist

Immigration

Global mobility

Program management

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 Upwork.com and follow us on LinkedIn, Facebook, Instagram, TikTok, and X; and learn more about Lifted at Go-Lifted and follow on LinkedIn.

As a Senior People Operations Specialist, you will play a key role in delivering thoughtful, scalable people programs and operational support across the employee lifecycle. As part of our People Operations team, you’ll combine strong operational expertise with the judgment and partnership skills needed to support HR Business Partners, managers, and employees through both day-to-day needs and more complex people matters.

You’ll own and continuously improve key people programs and processes, with a particular focus on employee lifecycle operations, immigration and global mobility, performance management, and HRBP enablement. You’ll serve as a subject matter resource in areas of expertise while building breadth across the broader People Operations portfolio.

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.

What it takes to catch our eye

• 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.

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 Q4 2026. 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.

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The annual base salary range for this position is displayed below. The range displayed reflects the minimum and maximum salary for this position, and individual base pay will depend on your skills, qualifications, experience, and location. Additionally, this position is eligible for the annual bonus plan or sales incentive plan and eligibility to participate in our long term equity incentive program.