Benefits Specialist

• 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

SpotOn 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 SpotOn 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.

About the Role

• 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

About You

• 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 legislation

Benefits

At SpotOn, we put people above everything else. We’re known for our innovative software and technology solutions, but we stand out because of the hard-working humans behind the tech. We can’t take care of our clients without taking care of our employees first, and that’s why we invest in you with a competitive benefits package which includes:

• Medical, Dental and Vision Insurance 
• 401k with company match
• RSUs
• Paid vacation, 10 company holidays, sick time, and volunteer time off
• Employee Resource Groups to build community and inclusion at work
• Monthly cell phone and internet stipend
• Tuition reimbursement for up to $2,000 per calendar year to assist with your professional development

Compensation

• Our base pay range starts at $65,000 -$85,000 for this role
• Please note the salary range listed is just one component of a competitive compensation package which includes a company stock plan
• Offers will be reflective of the candidate’s location and experience.

We will never ask candidates to pay fees, purchase equipment, or share sensitive personal or financial information during the hiring process. All legitimate communication from our recruiting team will come from an official company email address (@spoton.com). If something seems suspicious, please contact us at careers@spoton.com. 

SpotOn is an equal employment opportunity employer. Qualified candidates are considered for employment without regard to race, religion, gender, gender identity, sexual orientation, national origin, age, military or veteran status, disability, or any other characteristic protected by applicable law.

SpotOn is an E-Verify company.