Senior Payroll & Benefits Partner — Remote-First

First Stop Health; Chicago (IL); On-site; USD 90,000 - 120,000; Full time

Benefits offered by this job

Remote-first

Flexible paid time off

401k with employer match

Monthly phone stipend

Membership benefit

Job summary

First Stop Health is seeking a Senior Payroll & Benefits Partner to own payroll, benefits, and leave programs across our rapidly growing organization. You will partner with Finance, IT, Compliance, and external vendors to ensure accuracy, compliance, and efficiency in People Operations.

The role emphasizes independent judgment, operational excellence, and strategic process improvements while maintaining trust and confidentiality in a remote-first environment.

Qualifications

• Demonstrated ability to own payroll and benefits operations with independent impact.
• Strong cross-functional collaboration with Finance, IT, Compliance, and vendors.
• Excellent communication and customer-focused mindset.
• Experience implementing automation to improve processes.
• Experience managing payroll/benefits in multi-state organizations.

Responsibilities

• Own end-to-end payroll administration and processing.
• Oversee benefits, leave programs, and related People Ops processes.
• Partner with Finance for budgeting, audits, and reporting.
• Manage relationships with payroll providers, carriers, and vendors.
• Drive process improvements and standardize SOPs across workflows.
• Collaborate with Legal, Security, Data & Analytics on key initiatives.
• Produce payroll, benefits, compliance, and workforce reporting.

Skills

Operational excellence

Cross-functional partnership

Communication

Project management

Analytical capabilities

Confidential information handling

Job description

First Stop Health is seeking a Senior Payroll & Benefits Partner to own payroll, benefits, and leave programs across our rapidly growing organization. You will partner with Finance, IT, Compliance, and external vendors to ensure accuracy, compliance, and efficiency in People Operations.

The role emphasizes independent judgment, operational excellence, and strategic process improvements while maintaining trust and confidentiality in a remote-first environment.