Benefits & Leave Associate

About the Role:
Reporting to the HR Operations Manager, the Benefits & Leave Associate plays a key role in supporting the day-to-day execution of OppFi’s employee benefits and leave of absence programs. This role is responsible for driving accurate benefit enrollment, auditing and reconciling data, supporting compliance initiatives, and enhancing employee understanding and engagement with benefits and leave programs.

The ideal candidate brings strong analytical thinking, a high degree of intellectual curiosity, and a desire to understand and navigate the complexities of leave administration. This person thrives on details, takes initiative to solve problems, and delivers exceptional service to employees while ensuring compliance and accuracy.

What You’ll Do:

• Support the administration of OppFi’s employee benefit programs, including medical, dental, vision, life and disability insurance, 401(k), wellness, and voluntary offerings.
• Serve as a key point of contact for employee inquiries related to benefits and leave, delivering accurate, empathetic, and timely support across channels including email, Slack, and virtual meetings.
• Coordinate with third-party vendors to facilitate all aspects of the leave of absence process (e.g., FMLA, state and local leaves, ADA, parental leave), including tracking leave status, communicating timelines and expectations, and ensuring accurate pay and benefits continuation.
• Audit leave-related pay, time tracking, and benefits eligibility to ensure alignment with internal policies and legal requirements.
• Support payroll alignment for employees on leave, including paid leave calculations and coordination with finance/payroll teams.
• Drive employee engagement and awareness of benefits and leave programs through clear, consistent communications—including new hire orientation, Town Halls, intranet content, Slack posts, and wellness campaigns.
• Partner on the planning and execution of annual Open Enrollment, including testing systems, preparing communications, tracking participation, and auditing post-enrollment data.
• Conduct routine enrollment and billing audits to validate benefit elections, payroll deductions, and carrier invoices; investigate and resolve discrepancies.
• Support annual compliance activities including ACA reporting, 5500 filings, nondiscrimination testing, and audits (401k, workers' compensation, etc.).
• Ensure compliance with federal and state benefit and leave regulations (FMLA, COBRA, HIPAA, ERISA, etc.).
• Collaborate with HRIS and vendor teams to support benefit data feeds, interfaces, and integrations (e.g., UKG).
• Maintain thorough and up-to-date documentation for internal procedures, FAQs, and process guides.
  Troubleshoot and resolve benefits issues in coordination with vendors to ensure a seamless employee experience.

What you will bring to the team:

• 2–4 years of experience supporting benefits and leave of absence programs.
• Solid understanding of federal and state compliance requirements (FMLA, ADA, COBRA, ACA, ERISA, etc.).
• Intellectual curiosity and analytical thinking with a drive to understand the "why" behind complex policies and processes.
• High attention to detail and comfort working with data to identify discrepancies and trends.
• Proficiency in Excel (e.g., VLOOKUPs, pivot tables, data validation) for audits and analysis.
• Experience with HRIS systems such as UKG, Workday, or Paycor.
• Strong written and verbal communication skills, with the ability to clearly and effectively deliver information to broad audiences.
• A service-oriented mindset and ability to provide clear, empathetic support to employees at all levels.
• Organized and self-motivated with a sense of ownership over day-to-day responsibilities.

Reports to:  HR Operations Manager

Job Level:  Associate