Senior Benefits Analyst Americas

Job Description Summary

Cloud Software Group is seeking an experienced Benefits Analyst to support the day-to-day administration of employee benefits, Leave of Absence (LOA), and the global workplace accommodations process. Reporting to the Global Director, Benefits, this role is responsible for administering benefit programs, coordinating leave and accommodation cases, ensuring compliance with applicable regulations, and delivering an exceptional employee experience.

The ideal candidate is detail-oriented, customer-focused, and thrives in a fast-paced environment. This role partners closely with HR, Payroll, HRIS, Finance, Legal, external vendors, managers, and employees to ensure benefits, leave, and accommodation programs are administered accurately, efficiently, and in compliance with applicable laws and company policies.

Leave of Absence Administration

• Administer day-to-day Leave of Absence (LOA) programs across the Americas, with primary responsibility for the United States and Canada and support for regional leave programs as applicable.

• Coordinate employee leave requests, including FMLA, state and provincial leave programs, Short-Term Disability, Long-Term Disability, Parental Leave, Military Leave, Personal Leave, and other statutory and company-sponsored leave programs.

• Serve as the primary point of contact for employees, managers, HR Business Partners, Payroll, and third-party leave administrators regarding leave processes and requirements.

• Review leave documentation for completeness and coordinate with employees and vendors to obtain additional information when needed.

• Monitor leave status, return-to-work dates, benefit continuation, and payroll impacts.

• Maintain accurate leave records in Workday and vendor systems.

• Ensure compliance with applicable leave laws and company policies.

• Support the interactive accommodation process as appropriate.

Global Accommodations Administration

• Administer the company's global workplace accommodations process in accordance with company policy and applicable local laws.

• Coordinate accommodation requests submitted through Workday and ensure requests are processed accurately, timely, and confidentially.

• Review accommodation requests and supporting documentation for completeness and obtain additional information when necessary.

• Partner with People Business Partners, managers, Legal, and other stakeholders throughout the interactive accommodation process.

• Coordinate implementation of approved accommodations and communicate with appropriate stakeholders.

• Maintain confidential accommodation records in Workday.

• Track accommodation requests, approvals, denials, renewals, and periodic reviews.

• Respond to employee and manager questions regarding the accommodation process.

• Support administration of ergonomic, return-to-work, and other medically supported workplace accommodations.

• Assist with maintaining accommodation procedures, communications, forms, and documentation.

• Ensure accommodation administration complies with applicable laws and company policies.

Benefits Administration

• Administer day-to-day health and welfare benefit programs across the Americas.

• Process enrollments, qualifying life events, new hires, terminations, and status changes.

• Audit benefit transactions and reconcile eligibility files.

• Partner with Payroll, HRIS, and vendors to resolve discrepancies.

• Assist with benefits invoice reconciliation and billing reviews.

• Support annual Open Enrollment activities.

• Maintain accurate benefit records in HRIS and vendor systems.

Employee Support

• Serve as a primary point of contact for employee questions regarding benefits, leave, and accommodations.

• Provide accurate, timely, and professional customer service while maintaining confidentiality.

• Educate employees on benefit plans, leave programs, and accommodations.

• Resolve issues by coordinating with internal partners and external vendors.

• Develop and maintain employee-facing documentation, FAQs, and knowledge articles.

Compliance & Operational Excellence

• Ensure benefits, leave, and accommodation administration complies with applicable regulations.

• Maintain documentation supporting audits and compliance activities.

• Assist with annual compliance reporting.

• Follow established procedures and internal controls.

• Identify opportunities to improve efficiency and employee experience.

• Participate in system testing, documentation, and operational enhancements.

Cross-Functional Collaboration

• Partner with HR Business Partners, Payroll, HRIS, Finance, Legal, and external vendors.

• Coordinate with third-party administrators to resolve issues.

• Participate in operational projects, system updates, and process improvements.

• Maintain strong working relationships with stakeholders and vendors.

Qualifications - Required

• Bachelor's degree or equivalent combination of education and experience.

• Minimum of 5 years of experience administering employee benefits and Leave of Absence programs.

• Experience administering workplace accommodations and participating in the interactive accommodation process, preferably within a global organization.

• Strong knowledge of U.S. employee benefits, FMLA, ADA, state leave programs, disability administration, and related regulations.

• Experience working with third-party leave administrators and insurance carriers.

• Experience using Workday or another HRIS platform.

• Strong organizational, analytical, customer service, and communication skills.

• Ability to manage multiple priorities while meeting deadlines.

• Proficiency with Microsoft Office or Google Workspace, particularly Excel/Sheets.

Qualifications - Preferred

• Experience supporting employee benefits in Canada, Costa Rica, or Brazil.

• Experience supporting Open Enrollment.

• Knowledge of retirement and wellness programs.

• CEBS, PHR, SHRM-CP, or related certification.

• Spanish and/or Portuguese language skills are a plus.

Success Profile

The successful candidate is a dependable benefits professional who consistently delivers accurate, timely, and compliant benefits, leave, and accommodations administration. They provide exceptional customer service, maintain strong attention to detail, effectively manage competing priorities, and build collaborative relationships with employees, HR partners, Payroll, and external vendors. They are committed to operational excellence, continuous improvement, and creating a positive employee experience.

About Us:

Cloud Software Group is one of the world’s largest cloud solution providers, serving more than 100 million users around the globe. When you join Cloud Software Group, you are making a difference for real people, each of whom count on our suite of cloud-based products to get work done — from anywhere. Members of our team will tell you that we value passion for technology and the courage to take risks.  Everyone is empowered to learn, dream, and build the future of work. We are on the brink of another Cambrian leap -- a moment of immense evolution and growth. And we need your expertise and experience to do it. Now is the perfect time to move your skills to the cloud.

Cloud Software Group is firmly committed to Equal Employment Opportunity (EEO) and to compliance with all federal, state and local laws that prohibit employment discrimination. All qualified applicants will receive consideration for employment without regard to age, race, color, creed, sex or gender, sexual orientation, gender identity, gender expression, ethnicity, national origin, ancestry, citizenship, religion, genetic carrier status, disability, pregnancy, childbirth or related medical conditions (including lactation status), marital status, military service, protected veteran status, political activity or affiliation, taking or requesting statutorily protected leave and other protected classifications.

If you need a reasonable accommodation due to a disability during any part of the application process, please contact us via the Bridge portal for assistance.