Global Benefits Specialist

• →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.

What Sets You Up for Success

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.

• Employee-first mindset with a strong sense of ownership and follow-through;
• Strong organizational and problem-solving skills;
• Clear communicator who can explain complex topics in a simple and approachable way;
• Collaborative team player comfortable working cross-functionally;
• Comfortable navigating ambiguity and evolving processes;
• Eager to grow — you’re curious about benefits, open to feedback, and motivated to keep improving.

• Best All-In-One Hotel Management System | HotelTechAwards (2025)
• Overall 10 Best Places to Work | HotelTechAwards (2025)
• Most Loved Workplace® Certified (2024) 
• Top 10 People’s Choice(2024)
• Deloitte Technology Fast 500 (2024)

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 (including pregnancy, childbirth, or related medical conditions), 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.

Cloudbeds is committed to the full inclusion of all qualified individuals. As part of this commitment, Cloudbeds will ensure that persons with disabilities are provided reasonable accommodations in the hiring process. We encourage deaf, hard of hearing, deaf-blind, and deaf-disabled individuals to apply. If reasonable accommodation is needed to participate in the job application or interview process or to perform essential job functions, please contact our HR team by phone at (858) 201-7832 or via email at accommodations@cloudbeds.com. Cloudbeds will provide an American Sign Language (ASL) interpreter where needed as a reasonable accommodation for the hiring processes.

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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