Senior Benefits Analyst in New York at Jobgether

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Senior Benefits Analyst based in United States.

This role serves as a key operational owner for employee benefits across the United States and Canada.
You will oversee day-to-day administration of health, welfare, retirement, leave, disability, and related programs.
The position combines employee support, benefits systems administration, vendor management, compliance, and process improvement.
You will work closely with employees, managers, HR, payroll, HRIS, carriers, and third-party administrators.
Your work will help ensure accurate benefits delivery, regulatory compliance, reliable data, and a positive employee experience.
The role offers significant ownership in a fast-paced environment where priorities evolve and operational excellence is highly valued.
You will also contribute to projects, automation, reporting, and continuous improvements across the broader benefits function.

• Administer U.S. and Canadian employee benefit programs, including medical, dental, vision, HSA, FSA, retirement plans, life insurance, disability, AD&D, critical illness, accident, and other voluntary benefits.

• Manage enrollment, eligibility, life events, terminations, and related benefit transactions accurately and within established timelines.

• Audit and reconcile benefit data across Workday, payroll, insurance carriers, third-party vendors, and other systems, resolving discrepancies and data-quality issues.

• Support annual open enrollment, including planning, communications, system testing, execution, and post-enrollment reconciliation.

• Coordinate the implementation of new benefit programs, plan changes, vendor implementations, renewals, and operational transitions.

• Serve as a primary resource for employee and manager questions, providing clear, timely, professional, and empathetic guidance on benefits and leave programs.

• Research and resolve complex benefits issues in collaboration with vendors, carriers, payroll, HR Business Partners, and internal stakeholders.

• Develop and maintain benefits knowledge articles, FAQs, policies, procedures, employee resources, and operational documentation.

• Coordinate U.S. leave administration with third-party administrators, including leave tracking, return-to-work activities, timelines, status changes, and payroll coordination.

• Administer Canadian statutory leave programs in accordance with applicable provincial requirements.

• Coordinate disability administration and employee communications throughout the leave lifecycle, partnering with HR Business Partners on complex cases.

• Support benefits-related business processes, eligibility rules, event processing, security, and system configuration.

• Partner with HRIS and Payroll to troubleshoot system issues, conduct testing, improve processes, and maintain data integrity.

• Coordinate carrier file testing and ongoing eligibility file management.

• Support workers' compensation administration, including claim tracking, reporting requirements, payroll impacts, return-to-work activities, and documentation.

• Support benefits reporting, audits, annual compliance activities, plan documentation, required notices, and employee communications.

• Analyze employee inquiries, leave utilization, operational metrics, and other trends to identify root causes and recommend process improvements or automation opportunities.

• Participate in benefits projects and cross-functional initiatives that improve operational efficiency and the overall employee experience.

• Bachelor’s degree in Human Resources, Business Administration, or a related field; a master’s degree is preferred.

• 3–5 years of progressive HR experience, including hands-on benefits or people operations experience.

• Demonstrated experience administering employee benefits across both the United States and Canada.

• Strong understanding of health and welfare benefits, with knowledge of retirement plan administration, leave of absence, and disability processes.

• Working knowledge of benefits compliance requirements applicable in the U.S. and Canada.

• Experience administering HRIS platforms, preferably Workday, along with the ability to work across multiple systems and vendor platforms.

• Strong analytical and problem-solving skills, including the ability to reconcile data across systems, identify discrepancies, investigate root causes, and develop practical solutions.

• Exceptional attention to detail, data accuracy, organization, and documentation.

• Excellent interpersonal and customer-service skills, with the ability to build trust and communicate effectively with employees, managers, vendors, and stakeholders at all levels.

• Ability to explain complex benefits concepts clearly and handle sensitive employee matters with professionalism, discretion, and empathy.

• Strong written and verbal communication skills.

• Ability to influence cross-functional stakeholders, take ownership of challenges, and drive issues through to resolution.

• Highly organized and able to manage multiple priorities, systems, projects, and deadlines in a changing environment.

• Process-oriented mindset with an interest in continuous improvement, automation, and operational efficiency.

• Ability to adapt quickly to shifting business priorities while maintaining composure and high service standards.

• HR certification such as SPHR, SHRM-SCP, CHRP, or CHRL is preferred.

• Base salary of $90,000–$103,000 USD annually.

• Full-time, remote position.

• Opportunity to work across U.S. and Canadian benefits operations.

• Inclusive workplace focused on diversity of thought, experience, and background.

• Exposure to benefits, HRIS, payroll, leave, compliance, vendor management, and cross-functional HR initiatives.

• Opportunities to contribute to process improvement, automation, and employee-experience initiatives.

• Collaboration with HR, payroll, HRIS, vendors, carriers, and business stakeholders across the organization.