Senior Benefits & Payroll Specialist—Self-Insured Plans

Join Parachute, LLC; Austin (TX); On-site; USD 85,000 - 115,000; Full time

Job summary

Join Parachute, LLC in Austin, TX is seeking a Senior Benefits Specialist to own end-to-end benefits and payroll operations for a 1,000–2,000+ employee organization. You will oversee self-insured benefits, 401(k), and payroll processes across multiple locations, ensuring accurate invoices, reconciliations, and compliance.

As the primary benefits contact, you will educate employees, coordinate with the broker on claims trends, and collaborate with finance to deliver cost-effective plans while

Qualifications

• 5+ years of benefits experience, including self-insurance management.
• Payroll experience in multi-state, multi-location environments.
• Experience with 750+ employee population.
• Strong knowledge of federal/state payroll tax and wage & hour compliance.
• Hands-on experience with benefits reconciliation.
• Working knowledge of payroll accounting: journal entries, GL reconciliation, accruals.
• Experience serving as a benefits point of contact for employees, including plan education and open enrollment support.
• Experience working with benefits brokers/carriers on invoice reconciliation, eligibility audits, and claims issues.

Responsibilities

• Administer all aspects of our self insured benefits program, including enrollment, deductions, and reconciliation.
• Serve as the primary resource for all employees on benefits questions — medical, dental, vision, FSA/HSA, life, and disability — providing timely, accurate guidance and escalating complex issues appropriately.
• Reconcile benefits invoices monthly against the active employee census to confirm the company is billed only for active, eligible employees; resolve discrepancies directly with the broker and carriers.
• Review benefits activity to the general ledger each month to ensure premiums, employer/employee contributions, and accruals are recorded accurately.
• Partner with the broker to resolve enrollment, billing, eligibility, and claims issues as they arise.
• Track claims history and utilization trends over time; use this data to partner with the broker on renewal strategy and plan design.
• Lead employee education efforts (open enrollment communications, benefits fairs, one‑on‑one guidance) aimed at improving benefits literacy and driving down costs over time.
• Serve as the backup Payroll Admin, providing support with hourly, salaried, and contractor payroll processing, troubleshooting, and continuity of operations as needed.
• Likely opportunity to take on additional ownership of key People functions, including Workers' Compensation and/or Leave of Absence administration, based on team priorities, capacity, and business needs.

Skills

Benefits management

Payroll experience

Multi-state payroll

Wage & hour compliance

Benefits reconciliation

Payroll accounting

Broker liaison

Rippling

UMR

Pareto

Open enrollment education

Tools

Rippling

UMR

Pareto

Job description

Join Parachute, LLC in Austin, TX is seeking a Senior Benefits Specialist to own end-to-end benefits and payroll operations for a 1,000–2,000+ employee organization. You will oversee self-insured benefits, 401(k), and payroll processes across multiple locations, ensuring accurate invoices, reconciliations, and compliance.

As the primary benefits contact, you will educate employees, coordinate with the broker on claims trends, and collaborate with finance to deliver cost-effective plans while