Leave Specialist

We’re Patriot Software - a remote‑first, product‑led tech company on a mission to make accounting and payroll fast, simple, and affordable for millions of American businesses. With 175+ team members across the U.S. and a collaborative office hub in Canton, Ohio, we’re building software that empowers the backbone of the American economy.

• Job Title: Benefits & Leave Specialist
• Job Status: Full Time
• Location: Canton, OH (Hybrid)
• Position Type: Direct Hire, not a contract role
• Pay Range: $62,000 - $75,000 based on experience
• Schedule: 9:00 am – 5:00 pm EST, Monday through Friday

We’re hiring a Benefits & Leave Specialist to own the administration of employee benefits programs and leave of absence management across our U.S. workforce. You will partner closely with People Operations, Finance, Legal, and managers across the company, bringing precision and empathy to sensitive employee situations.

• Administer employee benefits programs end‑to‑end: enrollments, life events, qualifying status changes, billing reconciliation, and employee questions
• Serve as the primary point of contact for employee benefits inquiries, resolving issues related to eligibility, claims, and carrier escalations
• Conduct benefits orientation for new hires and support open enrollment planning and execution
• Own ACA tracking, compliance reporting, and 1095‑C preparation
• Reconcile monthly benefits invoices and coordinate with Finance on discrepancies
• Maintain and audit benefits‑related records in the HRIS; ensure data accuracy at all times
• Monitor and communicate regulatory changes affecting benefits (ERISA, HIPAA, ACA, COBRA, etc.)
• Support Section 125 plan administration, including HSA and FSA accounts

• Administer all leave programs across a multi‑state U.S. workforce including FMLA, ADA accommodations, parental leave, short‑term and long‑term disability, and state‑specific leave laws
• Serve as the subject matter expert on multi‑state leave compliance, including state‑mandated paid leave programs and jurisdiction‑specific notice and documentation requirements
• Manage leave cases from initiation through return‑to‑work: issue notices, track eligibility, coordinate with employees and managers, and maintain complete documentation
• Partner with managers and on ADA interactive process, reasonable accommodation requests, and documentation
• Coordinate with third‑party leave administrators and disability carriers as applicable
• Handle workers’ compensation claim intake and coordination with timeliness and care
• Proactively monitor leave expirations and communicate next steps to employees and managers with appropriate urgency

• Lead new hire onboarding logistics end‑to‑end: coordinating schedules, new hire paperwork, I‑9 verification and E‑Verify compliance, benefits enrollment, and partnering with IT and hiring managers on system setup and first‑day readiness
• Maintain I‑9 records in compliance with federal retention requirements, including periodic I‑9 audits and re‑verification
• Assist with scheduling and coordinating performance review cycles: sending reminders, tracking completion status, and following up on outstanding reviews to ensure timely completion
• Aid in annual compliance audits, federal/state reporting (EEO‑1, etc.), and required notices
• Support offboarding, separation documentation, and final pay coordination
• Partner with the People Ops team to develop, update, and communicate HR policies and procedures related to benefits and leave
• Back up the senior recruiter as needed when multiple job postings are open

• 3–5 years of dedicated, hands‑on experience in benefits administration and leave of absence management
• Experience administering multi‑state leave programs and working knowledge of state‑specific paid leave laws, FMLA, ADA, COBRA, and state‑mandated programs across multiple U.S. jurisdictions
• Strong command of federal and state employment law as it pertains to leave and benefits: FMLA, ADA, ACA, ERISA, HIPAA, FLSA, COBRA, and a drive to stay current as laws evolve
• Experience with ACA compliance including tracking,…