Benefits and Leave Compliance Specialist

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 sensitive, confidential, and legally complex employee matters
• Proven ability to manage a high volume of concurrent cases without dropping the ball
• Clear, proactive communication with your team, including early notice of schedule changes or absences
• High School Diploma or GED required
• Consistent, reliable high-speed internet access and a dedicated, quiet workspace free from distractions

Nice to Have

• 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

Your First 90 Days

In your first 30 days, you'll learn our systems, policies, and active leave caseload, and we expect lots of questions. By day 60, you'll be managing live leave cases and benefit questions independently and bringing recommendations on new or complex situations. By day 90, you’ll be owning benefit and leave items and be the go-to resource for managers and People Operations.

Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

Location & Commitments:

• This position is open to all candidates who legally reside and are eligible to work in the United States. This position is currently not open to applicants in the following locations: Alaska, California, Hawaii, Washington D.C.
• Working hours are established by each team and department based on business needs. For this role, coverage is required 9:00 AM–5:00 PM ET. Your workday is scheduled around that window and typically includes a lunch break outside of it. Due to the nature of our business, we have busy seasons and “right-nows” that occasionally require working outside of core hours.

Equal Opportunity

Patriot Software is an equal opportunity employer. We make employment decisions based on qualifications, merit, and business needs. We do not discriminate against any employee or applicant on the basis of race, color, religion, creed, sex (including pregnancy, childbirth, and related medical conditions), sexual orientation, gender identity or expression, national origin, ancestry, age, disability, genetic information, military or veteran status, or any other characteristic protected by federal, state, or local law.

We are committed to providing reasonable accommodations to qualified individuals with disabilities and to applicants and employees with pregnancy-related limitations. If you need an accommodation during the application or interview process, please contact People Operations.

More Reasons to Love Patriot

Great products start with great people—which is why we invest in our team so they can do their best work. In addition to a culture that encourages innovation and ownership, our full-time employees enjoy a comprehensive suite of benefits designed to help our team thrive inside and outside of work.

• Paid time off, inclusive of vacation and sick time
• Paid holidays
• Medical, dental, and vision insurance
• Section 125 HSA and FSA accounts
• Benefits beginning the first of the month following hire
• Company-paid life, short-term, and long-term disability insurance
• 401(k) with company match
• Up-to-date hardware and equipment provided
• Flexible scheduling and opportunities for advancement
• Engaging and collaborative company culture
• Education reimbursement
• Home office setup stipend after introductory period

Are you ready to take the next step in your career?

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Privacy Notice To protect the privacy of our customers and employees, please do not include sensitive Personally Identifiable Information (PII)—such as Social Security Numbers, Dates of Birth, or W-2s—when submitting your application.

Use of AI in the Hiring Process Thank you for your interest in Patriot Software! To support a fair and efficient hiring process, we use AI-powered tools to assist with resume screening, note-taking, and interview insights. These tools help us evaluate candidates consistently and in compliance with EEOC and all applicable laws.

AI tools do not make hiring decisions—all decisions are made by our human hiring team. All applicants are evaluated based on their qualifications, skills, and experience.

By submitting your application, you acknowledge the following:

AI Usage

• AI may analyze an applicant's video, including facial expressions, as part of assessing position fit.
• AI tools may be used during interviews for note-taking, evaluating responses, and generating interview summaries.

On-Camera Video Interviews

• All interviews are conducted via video with cameras on to maintain compliance and security standards.
• Patriot is a camera-on company for all video interactions.

Photo Capture for Security

• If selected to interview, you may be asked to provide or have a photo captured.
• This photo is used only to verify that the same candidate is present throughout all interview stages.
• Photos are not shared externally, used for any other purpose, or stored after the interview process. They are securely disposed of once the process is complete.

Privacy & Data Use

• Any photos are used solely for candidate verification.
• Geolocation tools may be used only to verify your location and ensure interview integrity.
• All geolocation use is limited to security and compliance needs and follows all applicable privacy laws.