Benefits Specialist

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.