Benefits Specialist

Step Up For Students empowers families to pursue the most appropriate learning options for their children. We unite communities to provide scholarships that open doors to a stronger future. With this support, students can choose the right learning environment and access resources to reach their full potential.

 

Our culture is rooted in two core values:

• Everyone is an asset
• Every event is an improvement opportunity

 

These values guide how we work together and continuously improve. We expect every team member to bring these principles to life in their daily work.

 

The Benefits Specialist is responsible for the day-to-day administration of employee benefits programs, including health insurance, retirement plans, wellness initiatives, leave programs, and other ancillary benefits. This role ensures compliance with applicable laws and policies, serves as a key point of contact for employee inquiries, and works closely with vendors and internal stakeholders to ensure a smooth and positive benefits experience.

 

Location: Remote (United States)

 

Key Responsibilities:

• Demonstrated success and a proven track record in professional/life experience in specific job functions, projects, or industries. Military service can substitute for professional experience and/or formal education requirements.
• Administer day-to-day operations of employee benefits programs, including medical, dental, vision, life insurance, disability, FSA/HSA, and retirement plans.
•  Process benefit enrollments for new hires, manage life event changes, and coordinate benefit terminations.
• Lead the annual open enrollment process, including preparing communications, updating systems, assisting employees, and submitting data to vendors.
• Serve as the primary contact for employee questions related to benefits eligibility, coverage, claims, and plan details.
• Provide clear and timely communication to employees to support understanding and utilization of benefits.
• Work directly with insurance carriers and third-party vendors to ensure timely processing and issue resolution.
• Ensure compliance with applicable laws and regulations such as ERISA, COBRA, HIPAA, and the ACA.
• Maintain accurate documentation and records for all benefit plans and assist in the preparation of government filings (e.g., Form 5500).
• Reconcile monthly benefits invoices and resolve discrepancies with vendors or carriers.
• Identify opportunities for process improvements and assist with implementation of enhancements to the employee benefits experience.
• Prepare and analyze reports on benefits utilization, costs, and trends to support HR and leadership decisions.
• Participate in benefits-related projects, policy updates, and cross-functional HR initiatives as needed.

 

Qualifications:

• 2–5 years of experience in employee benefits administration or a similar HR function.
•  Experience with HRIS and benefits administration systems (e.g., Workday, Dayforce)
• Demonstrated success and a proven track record in professional/life experience in specific job functions, projects, or industries, and military service can substitute for the formal education requirements.

 

Key Competencies:

• Attention to detail; accurately processes benefits data, reconciles invoices, and ensures compliance with regulations without errors
• Communication skills; clearly explains complex benefits information to employees and stakeholders across various levels of the organization
• Customer service orientation; responds promptly and empathetically to employee inquiries, demonstrating patience and professionalism
• Analytical thinking; interprets benefits data and trends, identifies discrepancies, and recommends effective solutions
• Confidentiality and integrity; handles sensitive employee information with discretion and maintains a high level of trustworthiness
• Regulatory knowledge; maintains up-to-date understanding of benefits-related laws and ensures organizational compliance (e.g., ERISA, COBRA, ACA, HIPAA)
• Problem-solving; resolves issues with vendors, claims, and employee concerns efficiently and diplomatically
• Technology proficiency; uses HRIS and benefits administration systems effectively and is comfortable with tools like Excel for reporting and analysis
• Organizational skills; manages multiple tasks, deadlines, and annual processes (e.g., open enrollment) in a timely and structured way
• Collaboration; works well with HR team members, managers, finance, and external vendors to deliver seamless benefits support
• Process improvement mindset; continuously looks for ways to streamline benefits processes and enhance employee experience

 

Interview Process:

• Veriff Identity Verification
• Recruiter Video Interview
• Hiring Manager Video Interview

 

Why you’ll love working here:

• Award-Winning Culture:
  We’ve been named one of the Best Companies to Work For four years in a row by Florida Trend and Workforce Research Group and honored as one of the Healthiest Companies by Florida’s First Coast Worksite Wellness Council. Fast Company recognized us as one of the Best Workplaces for Innovators—proof that we foster an environment where big ideas and bold thinking are encouraged.
• Comprehensive Benefits:
  Enjoy medical, dental, and vision coverage, plus HSA, FSA, and Lifestyle Spending Accounts. We also offer a competitive 401(k) with company match to help you plan for the future.
• Flexibility & Work-Life Harmony:
  Remote work options and unique time-off programs—including 14 paid holidays, Care and Parental Leave, and our Flexible Leave policy.
• Growth & Development:
  From mentorship programs to management training and professional development opportunities, we invest in your career journey every step of the way.
• Supportive Professional Environment:
  Our dedicated coaching team is here to help you succeed, and employee-led committees give you a voice in shaping our workplace. Collaboration isn’t just encouraged, it’s how we work.

 

Working Conditions and Equipment Use:

• Work is performed indoors in a typical office environment - not substantially exposed to adverse environmental conditions.
• Valid driver license with proof of insurance.
• Must be able to lift up to fifteen (15) pounds.
• Frequent use of office machines to include telephone, computer, and printer.