Benefit & Leave Specialist

Who we are

Over 600 employees strong, Asure sees Human Capital Management (HCM) through the lens of entrepreneurs and executives with an owner’s mentality. We help businesses develop their “Human Capital” to get to the next level, stay compliant, and allocate their time, money and technology toward growth. Our HCM platform empowers more than 100,000 clients to build great teams and better manage their people while staying compliant in an ever-changing HR legislative landscape. Asure’s HCM offering includes Payroll & Tax, HR, and Time & Attendance software and HR Services ranging from online compliance tools to a fully outsourced HR department.

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.

How you will contribute

• 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)
• 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)
• 3–5 years of experience in benefits and/or leave of absence administration; multi-state experience preferred.
  
  

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
  
  

Our Mission

To provide Human Capital Management (HCM) software and services that help companies grow, while nurturing a culture of growth around us.

• Helping customers grow by getting the most from their human capital.
• Helping our employees grow personally and professionally.
• Growing relationships in our communities that inspire goodness.
• Grow shareholder value
  
  

Our Vision

Be the most trusted Human Capital Management resource to entrepreneurs everywhere.

Our Values

Reflect who we are and what we stand for as a company.

• Embrace Change
• Lead with Integrity
• Own the Outcome
• Deliver Awesome
• Be a Good Human
  
  

We are an equal opportunity employer.

NO AGENCIES PLEASE:

Any unsolicited resumes sent to Asure Software from a third party, such as an Agency, including unsolicited resumes sent to Asure’s mailing address, fax machine or email address, directly to employees or hiring managers will be considered Asure property. Asure will not pay a fee for any placement resulting from the receipt of an unsolicited resume.