Benefits & Leave Specialist

Patriot Software•Canton, OH

1d•$62,000 - $75,000•Hybrid

About The Position

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. 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. Our team lives by six core values that guide how we work, build, and serve: Be Customer Obsessed: We start with our customers and work backward to deliver exceptional value. Lead With Speed: We move fast, take smart risks, and stay ahead by acting boldly. Don’t Cut Corners: We own our technologies and operations to deliver a high-quality, end-to-end experience. Create a Better Us: We simplify, automate, spend wisely, and continuously improve. Follow The Golden Rule: We treat others with respect, invite feedback, and commit even when we disagree. Grow, Be a Leader: We expect leadership at all levels and pursue excellence as a high-accountability, high-trust team. If this sounds like a place where you’d thrive, keep reading—your next opportunity might be here. 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. We are looking for a team member with deep, hands-on experience in benefits administration and multi-state leave compliance who can prioritize time-sensitive issues, manage complexity with confidence, and bring both precision and empathy to sensitive employee situations. You'll partner closely with People Operations, Finance, Legal, and managers across the company. You are someone who learns tools quickly, is highly collaborative, and is genuinely excited about applying AI and automation to make People Operations work better for our team across the US. This is a hands-on role for someone who wants to stay in a true HR generalist path for the next 2–4 years and continue building depth in People Operations.

Requirements

3–5 years of dedicated, hands-on experience in benefits administration and leave of absence management.
Demonstrated experience administering multi-state leave programs, including 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 genuine drive to stay current as laws evolve
Experience with ACA compliance including tracking, reporting, and 1095-C coordination
Comfortable with HRIS and benefits administration platforms; specific tools matter less than your ability to learn them quickly and use them accurately
Sharp written and verbal communication: clear, direct, and human — especially when communicating with employees navigating difficult situations
High integrity when handling sensitive, confidential, and legally complex employee matters
Proven ability to manage a high volume of concurrent cases without dropping the ball
Experience in a fast-paced SaaS, tech, or high-growth environment preferred
A 2- or 4-year degree in HR, Business, or a related field, or equivalent demonstrated experience
High School Diploma or GED required
Consistent, reliable high-speed internet access and a dedicated, quiet workspace free from distractions

Nice To Haves

HR certification: PHR, SPHR, SHRM-CP, or CLMS (Certified Leave Management Specialist)
Life, Accident & Health Insurance License
Experience with Greenhouse ATS or Patriot Software Payroll & Accounting
Familiarity with state-specific paid family and medical leave programs (CA, NY, WA, MA, NJ, CT, OR, CO, etc.)

Responsibilities

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 (e.g., state PFL, PFML, sick leave laws) 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.