Two Chicks With A Side Hustle

Support OppFi employees by ensuring smooth administration of benefits and leave programs while helping drive compliance, engagement, and employee well-being.

About OppFi
OppFi is a tech-enabled digital finance platform partnering with banks to deliver transparent and responsible financial products to everyday Americans. With a mission rooted in financial inclusion and customer care, OppFi helps consumers often overlooked by traditional lenders build stronger financial health. Recognized as a 2025 Crain’s Fast 50™ company, and named on Built In’s 2025 Best Places to Work in Chicago, OppFi continues to earn top consumer ratings with a 4.5/5.0 Trustpilot score.

Schedule

  • Full-time, remote role
  • Reports to the HR Operations Manager

What You’ll Do

  • Administer benefits programs, including medical, dental, vision, life, disability, 401(k), wellness, and voluntary offerings
  • Serve as a key point of contact for employee questions related to benefits and leave with empathetic, accurate, and timely support
  • Coordinate with vendors on leave processes (FMLA, ADA, parental, state/local leaves), including pay, benefits continuation, and communications
  • Audit leave-related pay, time tracking, and benefits eligibility for compliance
  • Align payroll and finance for employees on leave
  • Drive employee awareness of benefits through orientations, Town Halls, intranet posts, and campaigns
  • Support annual Open Enrollment, from system testing to communication and auditing
  • Conduct audits to validate enrollments, deductions, and invoices; resolve discrepancies
  • Assist with compliance reporting (ACA, COBRA, ERISA, 5500 filings, nondiscrimination tests, etc.)
  • Partner with HRIS and vendors to support benefit data feeds and integrations
  • Maintain updated process documentation and FAQs

What You Need

  • 2–4 years of experience supporting benefits and leave programs
  • Strong understanding of compliance requirements (FMLA, ADA, COBRA, ACA, ERISA, etc.)
  • Analytical thinker with strong attention to detail and intellectual curiosity
  • Proficiency in Excel (VLOOKUPs, pivot tables, audits, data analysis)
  • Experience with HRIS systems such as UKG, Workday, or Paycor
  • Excellent written and verbal communication skills
  • Organized, self-motivated, and service-oriented mindset with empathy for employees

Benefits

  • Compensation range: $59,200 – $88,800 annually, plus performance-based bonuses and equity eligibility
  • Remote-first flexibility with generous paid time off
  • 401(k) matching program
  • Health coverage: medical, dental, and vision
  • Tuition reimbursement
  • Lifestyle perks including DoorDash DashPass, Figo pet insurance, Rocket Lawyer, LinkedIn Learning, and Fringe platform for lifestyle rewards

Join a team committed to equity, employee well-being, and continuous improvement—helping employees thrive at work and beyond.

Your HR career in benefits and leave starts here.


Happy Hunting,
~Two Chicks…

APPLY HERE