Overview
About SpotOn 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, SpotOn is the place for you.
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 atcareers@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.
#J-18808-Ljbffr
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, SpotOn is the place for you.
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 atcareers@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.
#J-18808-Ljbffr