Global Benefits Specialist

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Global Benefits Specialist based in Canada.

We are seeking a detail-oriented, analytical, and technology-savvy Global Benefits Specialist to support employee benefits and payroll operations across multiple countries and employment models. In this role, you will help ensure accurate benefits administration, reliable data, and a positive employee experience by coordinating processes across HR, Finance, Payroll, and external providers. You will investigate discrepancies, manage employee requests, and turn complex benefits information into clear, accessible resources. The position is ideal for someone with a strong operations background who enjoys solving problems, working with data, and exploring AI and automation tools. You will also have opportunities to develop expertise in global benefits, retirement programs, and employee well-being initiatives while collaborating with a fully remote, international team.

Accountabilities

Support benefits administration processes, including enrollments, qualifying life events, employee status changes, and terminations across HRIS, payroll, and vendor platforms.

• Reconcile payroll deductions, eligibility files, enrollment records, and insurance carrier invoices, investigating discrepancies and coordinating resolutions with Payroll, HR, Finance, and vendors.

• Serve as a reliable point of contact for employee benefits questions, managing requests from beginning to resolution and providing clear updates.

• Create and maintain employee-facing resources, including benefits guides, FAQs, knowledge-base articles, presentations, and short videos.

• Support virtual new-hire benefits orientations and employee education sessions.

• Test and help implement new technology, AI tools, automated workflows, and process improvements to reduce repetitive tasks and increase efficiency.

• Coordinate with brokers, insurance carriers, payroll providers, and Employer of Record (EOR) partners to ensure smooth benefits operations.

• Contribute to broader global benefits initiatives, including open enrollment, benefits renewals, retirement programs, leave coordination, billing audits, and country-specific benefits projects.

• Support employee well-being initiatives and help simplify complex benefits processes across regions.

Requirements:

• At least 3 years of experience in Customer Success, Customer Support, Finance, Sales Operations, HR, or another operational role.

• Previous benefits experience is an advantage but is not required; training and guidance will be provided.

• Strong Excel and analytical skills, with the ability to independently work with spreadsheets and data from multiple systems.

• Experience reconciling information, investigating discrepancies, validating results, and identifying data inconsistencies.

• Hands-on experience using AI tools to improve productivity, analyze information, or simplify workflows.

• Curiosity about automation, emerging technologies, and opportunities to improve operational processes.

• Excellent written and verbal communication skills, with the ability to explain complex information clearly.

• Experience creating presentations, guides, training materials, or other employee-facing resources.

• Confidence presenting to groups and facilitating virtual sessions.

• Strong ownership, organization, and problem-solving skills, including the ability to manage competing priorities and follow through independently.

• A people-first mindset, sound judgment, and discretion when handling confidential information.

• Ability to collaborate effectively with cross-functional teams and colleagues across different countries and time zones.

Nice to have:

• Experience with Workday or another Human Resources Information System (HRIS).

• Exposure to benefits administration or payroll operations.

• Experience supporting globally distributed teams or international benefits programs.

• Familiarity with U.S. benefits programs and Canadian retirement plans, including 401(k), RRSP, TFSA, or DPSP.

• Experience creating short videos or other engaging employee education content.

• Experience building, testing, or implementing AI agents and automated workflows.

Benefits:

• Remote-first work environment: Work remotely, with flexibility across eligible locations.

• Paid time off: Vacation and time off in accordance with local labor requirements.

• Fully paid parental leave: Support for new parents.

• Home office stipend: Financial support for setting up your home workspace, based on country of residency.

• Professional development: Access to learning courses through an internal development platform.

• Career growth opportunities: Manager training, skills development, knowledge-sharing initiatives, and continuous learning.

• Global collaboration: Opportunities to work with HR, Payroll, Finance, Legal, and external partners across multiple countries.

• AI and automation exposure: Opportunities to introduce creative ideas and use emerging technologies in practical projects.

• Global team environment: Collaborate with colleagues across more than 40 countries in a fully distributed organization.

How Jobgether works:

We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

Why Apply Through Jobgether?

Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.

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