Global Benefits Specialist

Cloudbeds

2d • $60,000 - $85,000 • Remote

About The Position

Cloudbeds is seeking a Global Benefits Specialist to support and scale benefits operations for its globally distributed workforce. This role involves global benefits administration, leave coordination, employee support, reconciliations, compliance, and cross-functional operational work. The specialist will partner with various teams and external vendors to ensure a positive benefits experience for employees worldwide. This is an opportunity to grow in global benefits administration, retirement programs, leave management, vendor partnerships, compliance, and employee education within a fast-growing global SaaS company.

Requirements

• 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.

Nice To Haves

• 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.

Responsibilities

• Support the administration of global employee benefits programs across multiple 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.
• Assist with planning and execution of global open enrollment cycles.
• Support employee communications, timelines, and system readiness activities for open enrollment.
• 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.
• 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.
• Maintain retirement-related procedures, documentation, and employee-facing resources.
• 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.
• 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.
• 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.
• 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.
• Support well-being initiatives.
• Identify opportunities for process improvements and operational efficiencies.
• Help maintain standardized procedures and internal documentation.

Benefits

• Remote First, Remote Always
• PTO in accordance with local labor requirements
• Monthly Wellness Fridays - enjoy an extra long weekend every month
• Full 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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed