Benefits Specialist

Overview

About Spot On. We’re not just building restaurant tech—we’re giving independent restaurants the tools to compete and win. From our award-winning point-of-sale to AI-powered profit tools, everything we do helps operators boost profit, work smarter, and keep their best people. And every solution is backed by real humans who actually give a sh
* t about helping restaurants succeed.

• Named the #1 Restaurant POS by G2 (Fall 2025), based on ratings from real users
• Rated the top-rated point-of-sale (POS) for restaurants, bars, retail, and small businesses by Capterra users
• Awarded Great Places to Work and Built In’s Best Workplaces for multiple years running

We move fast, care hard, and fight for independent restaurant operators to do what they love, and love doing it. If you’re looking to make an impact with heart and hustle, Spot On is the place for you.

Spot On is seeking a dedicated Benefits Specialist to support the administration of our employee benefits and leave programs. In this role, you ll play a crucial part in supporting employees during some of their most important life moments – from welcoming new team members to helping employees navigate medical leaves. Your expertise will directly impact employee satisfaction, retention, and overall well-being while ensuring Spot On maintains compliance with regulatory requirements.

The ideal candidate will be a detail-oriented problem-solver who thrives in a fast-paced environment while maintaining a providing a best in class employee experience.

This is a hybrid position. In our Chicago office 3x/week.

• Serve as primary contact for all employee inquiries regarding benefits, 401(k), and leave of absence programs
• Facilitate new hire benefits orientation sessions, guiding employees through available programs and enrollment processes
• Administer all benefit programs including life events processing and enrollment updates for medical, dental, vision, savings accounts, COBRA and other programs
• Support compliance activities including ACA reporting, ERISA notices, and data preparation for annual 5500 filings or nondiscrimination testing
• Assist with invoice reconciliations and benefit audits to ensure accurate billing and system data integrity
• Partner with benefits and leave vendors to resolve escalations, monitor service levels, and support ongoing process improvements
• Support annual U.S. open enrollment and international benefit renewal processes, including ADP system configuration, testing, and communication distribution
• Help develop employee-facing benefits materials and support wellness program campaigns through cross-functional coordination
• Process and manage benefits mail and documentation
• Identify opportunities to streamline processes and recommend program enhancements
• Coordinate leave of absence and workers compensation administration from initial employee notification through return-to-work, serving as liaison between employees, HR Business Partners, managers, and third-party administrator (Guardian)
• Monitor and track status of all leave requests and ADA accommodation cases
• Support bi-weekly pay validation by reviewing leave data and coordinating with Payroll to ensure accurate leave-related payments
• Manage LOA communication templates and resource guides to ensure clear communication on LOA processes

• 2+ years of experience in employee benefits and leave of absences administration
• Solid analytical abilities with experience in report generation, audit performance, and system/vendor discrepancy resolution
• Excellent communication skills with demonstrated ability to craft clear, empathetic messaging for diverse employee audiences
• Process improvement mindset with proven ability to identify gaps and collaborate on solutions with cross-functional teams
• Sound judgment and composure when handling sensitive situations with discretion and professionalism
• Absolute confidentiality in managing sensitive employee information
• Exceptional organizational skills with meticulous attention to detail
• Adaptability to thrive in fast-paced, agile environments
• Knowledge of federal and state employment laws including FMLA, ADA, COBRA, ERISA, and state-specific leave…