Why This Job is Featured on The SaaS Jobs
Benefits operations is a critical but often underexamined function in SaaS, where distributed workforces and rapid product and org changes can stress compliance, systems, and vendor ecosystems. This Lead Benefits Analyst remit spans the Americas and includes self funded health plans and leave programs, signalling a role positioned close to the operational backbone that keeps a large cloud software organization running reliably.
For a SaaS career, the role builds durable capability in scaling people operations through process design, controls, analytics, and cross functional execution. Ownership of Open Enrollment, vendor implementations, and HRIS adjacent improvements develops the kind of operational program management that translates across SaaS companies, especially those standardizing global processes while balancing local regulation. The emphasis on dashboards, claims trends, and operational metrics also aligns with the data driven decision making common in subscription businesses.
This position suits someone who prefers structured problem solving and is comfortable being the escalation point for complex cases where accuracy and judgment matter. It will appeal to professionals who like working across Legal, Payroll, Finance, HRIS, and external administrators, and who want a role where influence comes from subject matter depth and operational rigor rather than people management alone.
The section above is editorial commentary from The SaaS Jobs, provided to help SaaS professionals understand the role in a broader industry context.
Job Description
Key Responsibilities
Benefits Operations Leadership
- Lead the day-to-day operations of benefits programs across the Americas, ensuring accurate administration, regulatory compliance, and operational excellence.
- Serve as the regional operational lead for Benefits, driving improvements to processes, systems, controls, and service delivery.
- Contribute to departmental goals, operational planning, and annual benefits priorities by identifying opportunities to improve efficiency, scalability, and employee experience.
- Analyze operational performance and recommend enhancements that improve quality, compliance, and operational effectiveness.
Leave of Absence Program Leadership
- Serve as the Americas subject matter expert and operational owner for all Leave of Absence (LOA) programs, including statutory and company-sponsored leaves.
- Manage complex leave cases across the United States and Canada while supporting regional leave programs in Costa Rica and Brazil.
- Partner with Legal, Payroll, HR Business Partners, and third-party administrators to ensure compliant, consistent, and employee-focused leave administration.
- Monitor legislative changes and implement process and policy updates to maintain compliance across the region.
Benefits Administration & Compliance
- Administer self-funded health plans, retirement programs, wellness, disability, and other employee benefit programs across the Americas.
- Monitor claims experience, funding requirements, and cost trends for self-funded health plans in partnership with Finance and external vendors.
- Lead annual 401(k) operational compliance activities, including audits, nondiscrimination testing, government filings, and vendor coordination.
- Manage Workers' Compensation administration and regional reporting requirements.
- Ensure compliance with applicable federal, state, provincial, and local regulations governing employee benefit programs.
Project & Program Management
- Lead major operational initiatives including Open Enrollment, vendor implementations, system enhancements, and process improvement projects.
- Develop and manage project plans, coordinate cross-functional stakeholders, mitigate risks, and ensure successful project execution.
- Drive continuous improvement initiatives by leveraging automation, technology, analytics, and best practices.
Vendor & Cross-Functional Partnership
- Manage relationships with brokers, insurance carriers, third-party administrators, and benefits technology vendors.
- Monitor vendor performance, resolve complex operational issues, and recommend service improvements.
- Partner closely with HRIS, Payroll, Finance, Legal, and People Operations to ensure seamless benefits administration and issue resolution.
Employee Experience & Subject Matter Expertise
- Serve as the escalation point for complex employee benefits and leave inquiries requiring advanced technical expertise.
- Communicate complex or sensitive benefits information clearly, professionally, and with empathy.
- Develop employee communications, knowledge resources, and training materials that improve understanding of benefit programs.
- Provide guidance, coaching, and subject matter expertise to HR colleagues and team members while promoting operational consistency and best practices.
Analytics & Continuous Improvement
- Analyze benefits utilization, claims data, operational metrics, and employee feedback to identify trends and improvement opportunities.
- Develop dashboards, reports, and recommendations for leadership to support operational decision-making.
- Lead initiatives that improve efficiency, reduce operational risk, strengthen compliance, and enhance the employee experience.
Qualifications
Required
- Bachelor's degree or equivalent combination of education and experience.
- Minimum of 8 years of progressive experience administering employee benefits, preferably within a fast-paced, global or technology organization.
- Deep expertise in U.S. self-funded medical plans, Leave of Absence administration, 401(k) compliance, and employee benefits regulations.
- Experience managing benefits programs across multiple countries within the Americas; experience supporting Canada, Costa Rica, and Brazil is strongly preferred.
- Proven experience leading complex operational projects such as Open Enrollment, vendor implementations, or systems enhancements.
- Advanced knowledge of Workday, HRIS platforms, Google Workspace, virtual desktop environments, and vendor administration systems.
- Demonstrated ability to improve operational processes, influence cross-functional stakeholders, and manage projects with minimal oversight.
- Strong analytical, organizational, project management, and problem-solving skills.
- Excellent verbal and written communication skills with the ability to communicate effectively with employees, leadership, vendors, and cross-functional partners.
Preferred
- Professional certifications such as CEBS, CBP, PHR/SPHR, or SHRM-CP/SCP.
- Experience with benefits analytics, self-funded health plan financial management, and vendor performance management.
- Spanish and/or Portuguese language proficiency.
Success Profile
The successful candidate is recognized as a trusted subject matter expert who independently manages complex operational initiatives, influences decisions across multiple business functions, and drives continuous improvement in Benefits Operations. This individual exercises sound judgment in ambiguous situations, leads major cross-functional projects with limited oversight, and plays a critical role in ensuring the organization's benefits programs remain compliant, competitive, and operationally excellent across the Americas.
Compensation may vary depending on your location, qualifications including job-related education, training, experience, licensure, and certification, that could result at a level outside of these ranges. Certain roles are eligible for additional rewards, including annual bonus, and sales incentives depending on the terms of the applicable plan and role as well as individual performance.
NY generally ranges: $1-$100,000,000
CA generally ranges: $1-$100,000,000
All other locations fall under our General State range: $1-$100,000,000
Benefits may vary depending on the nature of your employment with Cloud Software Group and the country where you work. U.S. based employees are typically offered access to healthcare, life insurance and disability benefits, 401(k) plan and company match, among others. This requisition has no specific deadline for completion.
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.
Cloud Software Group will consider qualified applicants with a criminal history and conduct the recruiting process in accordance with the California Fair Chance Act, Los Angeles County Fair Chance Ordinance for Employers and San Diego Fair Chance Ordinance. For access to the laws see the following links: California FCA and Los Angeles FCO.
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.
