Benefit & Leave Specialist

asuresoftware; Nashville (TN); Hybrid; USD 60,000 - 80,000; Full time

Benefits offered by this job

Medical, Dental, Vision, HSA, FSA effective on day 1

Company paid Life Insurance, Long-Term Disability

401K Program with 3% safe harbor contribution

Employee Stock Purchase Program

Fitness Reimbursement Program

Self-Managed PTO

Job summary

AsureSoftware seeks a Benefit & Leave Specialist for a hybrid role responsible for administering employee benefits and leave of absence programs while ensuring compliance with laws. In this position, you will assist employees with inquiries about benefits and manage leave cases while collaborating with HR and payroll teams.

The ideal candidate has a Bachelor’s degree in HR, 3–5 years of relevant experience, strong communication skills, and a solid understanding of applicable regulations. This role offers a competitive benefits package effective from day one!

Qualifications

• 3–5 years of experience in benefits and/or leave of absence administration.
• Strong knowledge of employee benefits programs and applicable regulations.
• Ability to manage confidentiality and exercise sound judgment.

Responsibilities

• Administer employee benefits programs, including enrollments and claims.
• Manage leave cases from initiation through return-to-work.
• Communicate effectively with employees regarding sensitive situations.
• Ensure compliance with federal and state laws related to benefits.

Skills

Employee benefits administration

Leave of absence management

Strong communication skills

Analytical skills

Education

Bachelor’s degree in Human Resources or related field

Tools

HRIS systems

Microsoft Office (Excel, Word, Outlook)

Job description

The Benefit & Leave Specialist is responsible for administering employee benefits and leave of absence programs, ensuring compliance with applicable federal, state, and local laws while delivering a high level of service to employees. This role serves as the primary point of contact for benefits and leave inquiries, manages leave cases from initiation through return-to-work, and partners with HR, payroll, managers, and external vendors to ensure accurate and efficient program administration. The position plays a key role in supporting a positive employee experience while maintaining compliance and operational effectiveness.

This is a hybrid position and can be based at any of Asure's office locations including: Austin, TX; Santa Ana, CA; Nashville, TN; Tampa, FL; Rochester, NY; or Cherry Hill, NJ.

Responsibilities

• Administer day-to-day employee benefits programs, including enrollments, changes, life events, and terminations; coordinate with benefits vendors, brokers, and third-party administrators to resolve eligibility, claims, and coverage issues
• Maintain accurate employee benefits and leave data within HRIS, internal trackers, and related systems; manage leave cases from initiation through return-to-work, ensuring timely documentation, communication, and compliance
• Track leave usage and maintain accurate records; communicate effectively and empathetically with employees regarding benefits and leave matters, including sensitive situations
• Maintain accurate, confidential employee records and documentation; partner with Payroll to ensure accurate benefits deductions, leave pay, and premium processing
• Identify opportunities for process improvement and support implementation of enhancements
• Assist in developing and updating policies, procedures, and employee-facing materials
• Collaborate with HR team members on escalated employee matters related to benefits and leave
• Assist with audits, reporting, and compliance-related activities
• Ensure compliance with federal, state, and local laws, including FMLA, ADA, ERISA, COBRA, ACA, PDA, PFL and HIPAA
• Partner with managers and HR to support return-to-work planning and workplace accommodations
• Provide required notices and documentation in accordance with regulatory requirements
• Administer leave of absence programs, including FMLA, ADA accommodations, and applicable state and local leave laws
• Support open enrollment processes, including system setup, employee communications, and education
• Serve as the primary point of contact for employee inquiries related to benefits and leave, providing clear and accurate guidance

Qualifications

• Bachelor’s degree in Human Resources, Business Administration, or related field (or equivalent experience)
• 3–5 years of experience in benefits and/or leave of absence administration; multi-state experience preferred
• Strong knowledge of employee benefits programs (medical, dental, vision, life, disability) and applicable regulations, including FMLA, ADA, ERISA, COBRA, ACA, and HIPAA
• Understanding of payroll impacts related to benefits and leave administration
• Excellent written and verbal communication skills with a strong customer service orientation
• Strong analytical and problem‑solving skills, with the ability to interpret and apply policies, laws, and regulations
• Ability to meet deadlines in a fast‑paced environment and identify process improvements
• Ability to maintain confidentiality, exercise sound judgment, and work both independently and collaboratively
• High attention to detail with demonstrated accuracy in data management and documentation
• Proven ability to manage multiple priorities through strong organizational and case‑management skills
• Experience working with HRIS systems, benefits platforms, leave tracking tools, and Microsoft Office (Excel, Word, Outlook)

Benefits

• Medical, Dental, Vision, HSA, FSA – All effective on day 1!
• Company paid Basic Life Insurance, A+D, Long-Term Disability, and Short-Term Disability
• 401K Program with 3% safe harbor contribution
• Employee Stock Purchase Program
• Fitness Reimbursement Program
• Self-Managed PTO

We are an equal opportunity employer. All candidates must be legally authorized to work in the US, as we are unable to sponsor or transfer Visas at this time.