Benefits & Payroll Specialist – Remote

Support a mission-driven healthcare company by managing payroll, compliance, and benefits for a nationwide remote team.


About Pair Team
Pair Team is reimagining how Medicaid serves the most underserved populations. As a tech-enabled medical group, we deliver whole-person care—clinical, behavioral, and social—by partnering with community-rooted organizations. We’re one of the largest Enhanced Care Management providers in California and on track to build the nation’s largest clinically integrated network for high-need Medicaid members.

Our impact: 58% reduction in emergency department visits and 29% reduction in hospital admissions. We’re not just delivering care—we’re building the future of equitable healthcare.


Schedule

  • Full-time, remote position.
  • Reports to the People Operations Manager.
  • Must be authorized to work in the U.S.

Responsibilities

  • Process bi-weekly hourly payroll and semi-monthly salaried payrolls across multiple states.
  • Manage bi-weekly timecard approvals and support managers with reminders and troubleshooting.
  • Register and manage state and local payroll tax accounts in new jurisdictions.
  • Oversee U.S. benefits plans: enrollment support, billing, qualifying life events, and employee questions.
  • Partner with brokers to ensure compliance with federal and state benefit regulations.
  • Conduct audits of benefit programs, payroll deductions, and carrier data.
  • Support benefits open enrollment, audits, quarter-end, and year-end processes.
  • Drive benefit utilization through education and employee communications.
  • Maintain and improve payroll and benefit self-service resources.
  • Partner with People Operations to continuously optimize payroll and benefits processes as the organization scales.

Requirements

  • 2+ years managing multi-state payroll and benefits programs.
  • Experience supporting hourly teams with timecards and time-off tracking.
  • Knowledge of payroll tax regulations, LOA types, and employment laws.
  • Proficiency with Excel/Google Sheets, HRIS, and payroll platforms (Rippling a plus).
  • Excellent organizational, problem-solving, and communication skills.
  • Ability to handle confidential employee data with discretion.
  • Ownership mindset with the ability to thrive in a fast-paced, high-growth environment.
  • Passion for supporting vulnerable populations, including those experiencing homelessness, severe mental illness, and substance use disorder.

Compensation

  • Salary range: $90,000 – $100,000 per year.
  • Equity compensation package available.

Benefits

  • Flexible vacation policy + 12 paid holidays.
  • Comprehensive medical, dental, and vision coverage.
  • 401(k) through Guideline with company contributions.
  • 100% company-sponsored short- and long-term disability and life insurance.
  • Subsidized caregiver and backup childcare support via Wellthy.
  • $100/month work-from-home stipend + company-provided equipment.
  • Travel reimbursements for offsites/retreats.
  • Opportunities for rapid career progression.

Pair Team is an Equal Opportunity Employer. All qualified applicants will be considered without regard to race, color, religion, sex (including pregnancy, gender identity, and sexual orientation), national origin, marital status, age, disability, military service, or any other status protected by law.

Employment offers are contingent upon successful background checks. Pair Team participates in E-Verify.


Happy Hunting,
~Two Chicks…

APPLY HERE