Global Benefits Specialist

About the role

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

• 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;
• Career Growth: Gain exposure to benefits administration, retirement programs, leave management, vendor partnerships, compliance, and employee education across multiple countries and employment models within a fast-growing global SaaS company.

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.

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.

Pay

Depending on your skills and experience, you can expect your annual compensation to be between $60,000 – $85,000 USD.

Schedule

Remote First, Remote Always