[Hiring] Benefits and Leave Compliance Specialist @Patriot Software

Role Description

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.

Qualifications

• 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.
• 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.

Requirements

• HR certification: PHR, SPHR, SHRM-CP, or CLMS (Certified Leave Management Specialist) - Nice to Have.
• Life, Accident & Health Insurance License - Nice to Have.
• Experience with Greenhouse ATS or Patriot Software Payroll & Accounting - Nice to Have.

Benefits

• 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.