Payroll & Benefits Specialist – Remote (United States)

Help shape the future of equitable healthcare while supporting a nationwide remote team.

About Pair Team
Pair Team is reimagining Medicaid to better serve underserved populations. As a tech-enabled medical group, we provide whole-person care—clinical, behavioral, and social—through community partnerships. With AI-driven tools and automation, we scale meaningful, human-centered care that’s reducing ER visits and hospital admissions, while building the nation’s largest clinically integrated Medicaid network.

Schedule

  • Full-time
  • Fully remote (U.S.-based)
  • Standard business hours with flexibility
  • Reports to the People Operations Manager

What You’ll Do

  • Process bi-weekly hourly and semi-monthly salaried payroll for a nationwide remote team.
  • Manage payroll tax accounts and ensure compliance with state and local regulations.
  • Oversee U.S. benefits operations, including enrollment, billing, and employee support.
  • Partner with benefits brokers to ensure compliance with laws and drive benefit utilization.
  • Conduct audits of payroll, benefits, and carrier data for accuracy.
  • Support annual payroll and benefits cycles, including open enrollment and year-end.
  • Improve payroll and benefits processes to scale with growth.

What You Need

  • 2+ years of experience managing multi-state payroll and benefits.
  • Experience supporting large hourly populations with time cards/time-off.
  • Strong knowledge of payroll tax regulations, LOA administration, and employment laws.
  • Proficiency with payroll/HRIS systems (Rippling a plus), Excel/Google Sheets.
  • Exceptional attention to detail, organization, and analytical skills.
  • Strong communication skills and ability to explain payroll/benefits clearly.
  • Passion for Pair Team’s mission of serving individuals with complex chronic needs.

Benefits

  • Competitive salary: $90,000–$100,000
  • Equity package
  • Flexible vacation policy
  • Comprehensive medical, dental, and vision coverage
  • 401(k) with Guideline
  • 100% company-paid life, short- and long-term disability insurance
  • Backup childcare and caregiver support
  • $100/month work-from-home stipend and provided equipment
  • Career progression opportunities in a high-growth environment
  • Travel reimbursements for retreats and project needs

Make a direct impact by supporting the people who power equitable healthcare innovation.
Join Pair Team and help build the future of community-rooted care.

Happy Hunting,
~Two Chicks…

APPLY HERE