Senior Human Resources Generalist – Benefits & Leave Administration

Confidential search. This role is run discreetly through our retained executive search partnerships. The hiring organization, leadership structure and interview process are shared with qualified candidates as they progress through the search.

Confidential retained search. A leading financial services organization is seeking an experienced Senior Human Resources Generalist – Benefits & Leave Administration to provide leadership across benefits administration, leave management, HR operations, compliance, and employee support. This is a hands-on and leadership-focused HR opportunity for a professional who understands the complexity of employee benefits and leave programs and can translate regulatory requirements and HR policies into clear, effective processes for employees, managers, and leadership. Compensation: $95,000–$125,000+ base + performance bonus + comprehensive benefits.

What you'll do

• Lead and oversee benefits administration programs across the organization
• Manage benefits-related processes, workflows, enrollment activities, and employee support
• Identify opportunities to improve benefits utilization, employee satisfaction, and operational efficiency
• Partner with internal teams and external benefits providers to ensure accurate and timely service delivery
• Support leadership with benefits-related analysis, recommendations, and strategic decisions
• Monitor benefits processes and ensure appropriate documentation and controls are maintained
• Lead and administer complex leave-of-absence programs across the employee lifecycle
• Manage leave programs including FMLA, CFRA, PFL, PDL, PWEA, Military, Personal, Bereavement, Jury, Victim, Organ Donor, PTO, LTD, and STD
• Ensure leave administration is handled accurately, consistently, and in accordance with applicable policies and requirements
• Coordinate leave-related communication with employees, managers, HR leadership, and relevant external parties
• Track leave activity, documentation, deadlines, and return-to-work requirements
• Support compliance across benefits and leave administration programs
• Apply knowledge of ADA/ADAA, ERISA, HIPAA, COBRA, and other relevant HR regulatory frameworks
• Translate complex policies and regulatory requirements into practical guidance for employees and managers
• Maintain accurate records and documentation related to benefits and leave programs
• Build and improve systems, processes, and workflows supporting benefits and leave administration
• Identify operational inefficiencies and implement practical improvements
• Standardize processes to improve accuracy, consistency, and employee service
• Own reporting and performance metrics related to benefits and leave administration
• Monitor benefits costs, leave activity, compliance metrics, service levels, and operational performance
• Develop meaningful reporting for HR leadership and senior stakeholders
• Partner with the Director of Human Resources and senior leadership on benefits and leave strategy
• Provide clear guidance and support to employees and managers navigating complex benefits or leave matters
• Develop and mentor HR team members supporting benefits and leave administration

What we're looking for

• Strong professional experience in benefits administration and leave-of-absence management
• Demonstrated experience managing complex employee leave programs
• Working knowledge of FMLA, CFRA, PFL, PDL, PWEA, ADA/ADAA, ERISA, HIPAA, and COBRA
• Experience with benefits enrollment, employee support, HR processes, and benefits operations
• Proven ability to lead HR programs and deliver measurable operational outcomes
• Strong understanding of HR compliance and risk management
• Experience developing or improving HR processes, systems, and workflows
• Strong analytical and reporting capabilities
• Experience managing stakeholders and cross-functional HR initiatives
• Strong written and verbal communication skills
• Ability to translate complex HR policies and requirements into clear, actionable guidance
• Strong judgment, organization, attention to detail, and problem-solving skills
• Ability to operate effectively in a dynamic and evolving financial services environment

Nice to have

• SHRM-SCP, SPHR, or CEBS certification
• Experience with HRIS and benefits administration platforms
• Prior exposure to confidential or retained executive search processes
• Track record of building KPI dashboards and HR analytics for leadership