Global Benefits Specialist

Canada; North America

About the Position

At Cloudbeds, we're transforming hospitality with our intelligently designed platform that powers properties across 150 countries, processing billions in bookings annually. We're looking for a Global Benefits Specialist to help support and scale benefits operations across a globally distributed workforce spanning multiple countries, entities, and employment models.

This role combines global benefits administration, leave coordination, employee support, reconciliations, compliance, and cross-functional operational work. You’ll partner closely with Payroll, HR, Finance, brokers, insurance carriers, payroll vendors, and Employer of Record (EOR) providers to help ensure employees around the world receive accurate, timely, and well-supported benefits experiences.

Responsibilities

Benefits Administration

• Support the administration of global employee benefits programs across the U.S., Canada, Ireland, Brazil, Spain, and other international locations.
• Process enrollments, qualifying life events, status changes, and terminations across HRIS, payroll, and vendor platforms.
• Maintain accurate benefits records and identify discrepancies across systems.
• Coordinate with brokers, carriers, payroll providers, and EOR partners on day-to-day administration and employee inquiries.

Open Enrollment & Employee Education

• Assist with planning and execution of global open enrollment cycles.
• Support employee communications, timelines, and system readiness activities.
• Facilitate virtual new hire benefits orientations and employee education sessions.
• Create and maintain employee-facing materials, including benefits guides, FAQs, presentations, and enrollment resources.
• Support renewal preparation activities and utilization reporting.

Global Retirement Programs

• Support administration of global retirement and savings programs, including U.S. 401(k), Canadian RRSP/TFSA/DPSP plans, and other country-specific retirement or pension arrangements.
• Coordinate with retirement plan providers, brokers, Payroll, and Finance on enrollments, contribution processing, employee inquiries, and vendor-related matters.
• Assist with retirement plan audits, compliance reviews, annual filings, and documentation requests from auditors and vendors.
• Maintain retirement-related procedures, documentation, and employee-facing resources.

Employee Support

• Serve as a responsive and empathetic point of contact for employee benefits inquiries.
• Help troubleshoot enrollment, billing, eligibility, and vendor-related issues.
• Escalate complex cases appropriately while ensuring a high-quality employee experience.

Reconciliation & Compliance

• Assist with benefits billing reconciliations, enrollment, and 401(k) audits, eligibility reviews, and vendor invoice validation activities.
• Review deductions, eligibility files, and enrollment data across systems.
• Investigate discrepancies and document findings for resolution.
• Coordinate with Payroll and Finance to support accurate deductions and remittances.
• Support audit readiness and compliance documentation efforts.

Leave of Absence Support

• Support the administration of leave of absence programs, including FMLA, parental leave, disability, medical leave, and country-specific statutory leaves.
• Coordinate with leave administration vendors, Payroll, HR, and managers on leave timelines and payroll impacts.
• Maintain awareness of leave and benefits compliance developments impacting global employees.

Global & EOR Support

• Coordinate with Employer of Record (EOR) providers on country-specific benefits and statutory programs.
• Support benefits processes for international employees and contractors where applicable.
• Assist with documentation and process improvement initiatives across global benefits operations.

Well-being & Continuous Improvement

• Support well-being initiatives.
• Identify opportunities for process improvements and operational efficiencies.
• Help maintain standardized procedures and internal documentation.

Requirements

Required Qualifications

• 3–5 years of experience in benefits administration, HR operations, payroll operations, or a related field.
• Foundational knowledge of U.S. employee benefits programs, including medical, dental, vision, disability, life insurance, retirement plans, and leave administration.
• Experience supporting employee-facing benefits processes and inquiries.
• Strong attention to detail, particularly in reconciliations, audits, and cross-system reviews.
• Comfortable presenting information in employee orientations or virtual education sessions.
• Strong written and verbal communication skills.
• Ability to manage confidential and sensitive information with discretion.
• Comfortable working in a fast-paced, remote, and globally distributed environment.

Preferred Qualifications

• Experience supporting benefits programs across more than one country.
• Experience supporting retirement and savings programs, such as U.S. 401(k), Canadian RRSP/TFSA/DPSP plans, pension plans, or other country-specific retirement arrangements.
• Exposure to retirement plan audits, compliance testing, annual filings, or vendor management is a plus.
• Familiarity with Employer of Record (EOR) provider environments.
• HRIS experience - Workday preferred.
• Vendor coordination experience (brokers, carriers, leave administrators).
• Experience in a high-growth or global startup environment.
• CEBS, PHR, or equivalent HR/benefits certification or coursework.

We Offer

• Competitive salary: $60,000 – $85,000 USD annually.
• Remote First, Remote Always.
• PTO in accordance with local labor requirements.
• Monthly Wellness Fridays - enjoy an extra-long weekend every month.
• Fully Paid Parental Leave.
• Home office stipend based on country of residency.
• Professional development courses in Cloudbeds University.
• Access to professional development, including manager training, upskilling, and knowledge transfer.

About the Company

Behind Cloudbeds' revolutionary technology is a team of redefining what's possible in hospitality. We're 650+ employees across 40+ countries, bringing together elite engineers, AI architects, world-class designers, and hospitality veterans to solve challenges others haven't dared to tackle. Our diverse team speaks 30+ languages, but we all share one language: a passion for innovation and travel.

Cloudbeds is proud to be an Equal Opportunity Employer that celebrates the diversity in our global team! We do not discriminate based upon race, religion, color, national origin, gender, sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics.

To all Staffing and Recruiting Agencies: Our Careers Site is only for individuals seeking a job at Cloudbeds. Staffing, recruiting agencies, and individuals being represented by an agency are not authorized to use this site or to submit applications, and any such submissions will be considered unsolicited. Cloudbeds does not accept unsolicited resumes or applications from agencies. Please do not forward resumes to our jobs alias, Cloudbeds employees, or any other company location. Cloudbeds is not responsible for any fees related to unsolicited resumes/applications.

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