Benefits and Leave Compliance Specialist
Patriot Software · Remote
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.
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.
Summary:
- Job Title: Benefits, Leave & Compliance Specialist
- Job Status: Full-time
- Location: Remote
- Compensation: Salaried (Exempt)
- Position Type: Direct Hire; note, this is not a contract role
- Pay Range: $67,000 - $80,000 based on experience
- Core Hours: Coverage required 9:00 AM–5:00 PM ET. Your workday is scheduled around that window and typically includes a lunch break outside of it.
We’re hiring a Benefits, Leave & Compliance Specialist to own the administration of employee benefits programs and leave of absence management across our U.S. workforce. This is not a generalist benefits role; we’re looking for someone with deep, hands-on experience administering multi-state leave programs who treats regulatory research as a core part of the job, not an add-on. You should be the person who reads a new state leave law before it takes effect, flags the gap, and comes to the table with a recommendation.
You’ll partner closely with People Operations, Finance, Legal, and managers across the company. You learn systems quickly, work independently without being prompted, and are genuinely excited about applying AI and automation to make People Operations more efficient. This is a hands-on role for someone who wants to own a function — not just execute tasks — for the next 2–4 years to continue building depth in People Operations.
What this role looks like today: Our leave and benefits processes are largely manual and administered in-house. We evaluated third-party leave administrators and chose not to use one because they don't integrate with our systems. You'll do real data entry and case tracking by hand while building better processes over time. If you want to inherit a polished, automated function, this isn't that role. If you want to build one, it is.
What You’ll Be Doing:
Benefits Administration: 30%
- 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: 50%
- 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 — managers and People Ops should be able to bring you a question and get a clear, confident answer or a well-researched recommendation
- 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 state programs (e.g., NY DBL/PFL through NYSIF), disability carriers, and benefits vendors 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
General People Ops Support: 20%
- 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.
Please note this is a sample of what you’ll be doing. Your duties, responsibilities, and activities may change at any time with or without notice.
What You’ll Need
- 3-5 years of dedicated, hands-on experience in benefits administration and leave of absence management
- Demonstrated experience administering NY DBL/PFL or a comparable state statutory disability or PFML program (NJ, MA, WA, etc.), along with working knowledge of FMLA, ADA, COBRA, and state-specific leave laws across multiple jurisdictions
- A proven habit of staying current on multi-state leave law: you actively follow regulatory updates, track pending legislation, and don't wait to be told when something changes
- Proven ability to research a new leave law, assess its application to our workforce, and bring a clear recommendation — not just flag that something exists
- 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, use them accurately, and own them fully
- Sharp written and verbal communication: clear, direct, and human — including the ability to translate complex regulatory requirements into plain-language guidance for managers and employees
- Self-directed in practice: you ask clarifying questions early, bring your own questions and ideas to 1:1s without being prompted, identify your next priority when a task wraps up, and raise your hand quickly when you're stuck. You don't need someone to tell you a new PFML program passed or a leave expiration is coming; you build the systems to catch it yourself
- High integrity when handling sensitiv