Let Us Introduce Ourselves
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.
What We Believe In
Creating great products starts with creating an environment where people thrive. That means connection, clarity, growth, high trust, and a culture where ideas move quickly and quality matters.
What You’ll Be Doing
Benefits Administration
- 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
Leave of Absence Administration & Compliance
- Own leave compliance across all active employee jurisdictions — including staying ahead of new and pending state legislation and translating it into actionable guidance for the team
- Proactively monitor legislative and regulatory developments across all states where Patriot employees are located; assess impact, develop recommendations, and implement policy or process changes before deadlines hit
- Serve as Patriot’s internal subject matter expert on leave compliance
- 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
- 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 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
General People Ops Support
- Assist with scheduling and coordinating performance review cycles
- 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
What You’ll Need
- 3-5 years of dedicated, hands-on experience in benefits administration and leave of absence management
- Demonstrated, multi-state leave administration experience is required — including working knowledge of state-specific paid leave laws, FMLA, ADA, COBRA, and state-mandated programs
- Strong command of federal and state employment law: FMLA, ADA, ACA, ERISA, HIPAA, FLSA, COBRA
- Experience with ACA compliance including tracking, reporting, and 1095-C coordination
- Comfortable with HRIS and benefits administration platforms
- Proven ability to manage a high volume of concurrent cases
- High School Diploma or GED required