Benefits & Leave 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 Specialist
• Job Status: Full Time 
• Location: Canton, OH (Hybrid)
• Compensation: Salaried (Exempt)
• Position Type: Direct Hire, note, this is not a contract role
• Pay Range: $62,000 - $75,000 based on experience
• Schedule: 9:00am - 5:00pm EST, Monday through Friday.

What You’ll Be Doing: 

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.

Benefits Administration: 30–40%

• 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: 30–40%

• 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

General People Ops Support: 20-40%

• 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. 

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 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 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
• Familiarity with state-specific paid family and medical leave programs (CA, NY, WA, MA, NJ, CT, OR, CO, etc.)

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

Location & Commitments:

Direct Hire Hybrid role.  This position is not eligible for relocation benefits, and applicants must be willing to work in the Canton, OH headquarters 1-2 days per week. 

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, core working hours are typically between 9:00am - 5:00pm EST, Monday through Friday. Due to the nature of our businesses, we have busy seasons and “right-nows” that occasionally require working outside of core hours.

Patriot is an equal opportunity employer. We do not discriminate against any employee or job applicant on the basis of race, color, gender, national origin, age, religion, creed, disability or sex.

Equal Opportunity

Patriot is an equal opportunity employer. We do not discriminate against any employee or job applicant on the basis of race, color, gender, national origin, age, religion, creed, disability or sex.

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 that help our team thrive inside and outside of work. Learn more about our opportunities and benefits on our Careers page.

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

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Ready to take the next step in your career? We’d love to meet you.

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.