HR Generalist

This role will establish scalable processes, create documentation, ensure compliance, improve the employee experience, and build internal expertise through training and knowledge transfer. Serve as a primary resource for employee benefits inquiries, including medical, dental, vision, life insurance, disability, retirement, COBRA, wellness, and voluntary benefit programs.

HR Generalist Benefits and Leave Administration


Job Summary

Serve as the primary HR resource for complex benefits, disability, accommodation, and leave-related matters during a period of organizational transformation and growth. This role will establish scalable processes, create documentation, ensure compliance, improve the employee experience, and build internal expertise through training and knowledge transfer.

Responsibilities

• Serve as a primary resource for employee benefits inquiries, including medical, dental, vision, life insurance, disability, retirement, COBRA, wellness, and voluntary benefit programs.
• Support qualified life events, enrollment changes, benefits escalations, and complex employee benefit issues.
• Partner with benefits vendors, carriers, and internal stakeholders to resolve issues and improve the employee experience.
• Ensure accurate benefits transactions and data integrity within HR systems.
• Assist with annual open enrollment planning, execution, and employee education.
• Manage employee leave and accommodation cases, including FMLA, ADA, STD, LTD, parental bonding leave, personal leave, military leave, and state-specific leave programs.
• Serve as the primary HR liaison for employees, managers, and vendors throughout the leave lifecycle.
• Collaborate with Legal, Payroll, and Total Rewards teams to ensure regulatory compliance and effective administration.
• Provide guidance to leaders on complex leave, accommodation, and return-to-work situations.
• Coordinate documentation, communications, and employee case management activities.
• Evaluate benefits and leave processes to identify opportunities for increased efficiency, accuracy, and employee satisfaction.
• Develop and maintain SOPs, workflows, decision trees, manager guides, employee FAQs, and process documentation.
• Establish operational metrics and reporting to improve service delivery and compliance.
• Partner with HR Technology and Operations teams to optimize system functionality and reporting.
• Serve as the internal subject matter expert for benefits administration and leave management.
• Develop training materials and reference guides.
• Mentor and train an internal HR employee to become a benefits and leave management subject matter expert.
• Lead hands-on coaching sessions using real-world employee cases and scenarios.
• Create a comprehensive transition plan to support sustainable ownership after the engagement concludes.

Requirements

• Bachelor s degree in Human Resources, Business Administration, or a related field preferred.
• At least five years of progressive HR experience.
• At least three years of dedicated benefits administration and/or leave of absence experience.
• Strong working knowledge of FMLA, ADA and the interactive accommodation process, STD/LTD administration, COBRA, ERISA, HIPAA, and multistate leave laws and regulations.
• Experience partnering with third-party leave administrators, disability carriers, and benefits vendors.
• Experience working in HRIS platforms such as Workday, Paycom, or similar systems.
• Strong communication, consultation, and problem-solving skills.
• Ability to manage sensitive employee situations with professionalism, empathy, and confidentiality.
• Experience supporting a geographically dispersed workforce preferred.
• Experience in financial services, fintech, or another highly regulated industry preferred.
• Experience creating HR process documentation, training materials, and operational procedures preferred.
• Demonstrated success in knowledge transfer, coaching, and capability-building initiatives preferred.

Skill

• Benefits administration
• Leave of absence and ADA case management
• Employee accommodations and disability administration
• HRIS systems and data integrity
• Regulatory compliance
• Process improvement and documentation
• Vendor and stakeholder management
• Training, coaching, and knowledge transfer
• Communication, consultation, and problem-solving
• Confidential case management

Summary Qualification

• Experienced HR professional with specialized expertise in benefits administration and leave management.
• Knowledgeable in federal and state leave regulations, disability programs, accommodations, and benefits compliance.
• Skilled at managing complex employee cases and partnering with vendors and internal stakeholders.
• Capable of creating scalable processes, documentation, training materials, and operational metrics.
• Effective coach and mentor who can transfer knowledge and build internal HR capabilities.
• Committed to improving efficiency, compliance, employee satisfaction, and operational continuity.

Success Measures

• Become a trusted operational leader for benefits and leave administration.
• Manage complex benefits, leave, accommodation, and disability cases with strong compliance and employee satisfaction.
• Reduce escalations through proactive case management and effective vendor partnerships.
• Create comprehensive SOPs, workflows, templates, and job aids for key benefits and leave processes.
• Deliver structured training and ongoing mentorship to HR team members.
• Enable designated employees to independently manage routine and moderately complex benefits and leave matters.
• Implement improvements that increase efficiency, enhance the employee experience, and reduce operational risk.
• Complete a transition plan that supports sustainable internal expertise and operational continuity.

 

Wollborg Michelson Recruiting is an Equal Opportunity Employer and prohibits discrimination of any kind. We ensure job offers are made based of one s employment experience, skills, and qualifications, regardless of race, gender, ethnic origin, or any other classification protected by law. All applicants must furnish proper identification to prove their legal right to work in the US upon a job offer. We participate in E-Verify to confirm one s right to work in the US. Wollborg Michelson Recruiting does not provide sponsorship for an employment-based visa status.