# People Operations Manager (Benefits & Payroll) at Freewill

- Company: Freewill
- What the company does: FreeWill lets you make your last will and testament quick, easy, and completely free. It is a simple online legal will maker that helps you compile will forms to print and sign, or to take as a basic will template to an estate planning lawyer. FreeWill is... Backed by Pear VC and ICONIQ.
- Company website: https://www.freewill.com/
- Type: Startups
- Level: Senior
- Location: United States (Excluding AL, CO, LA)
- Work setup: Remote
- Pay: $95K to $105K base salary per year (USD)
- Posted: 2026-09-21
- Apply by: 2026-11-05
- Apply: https://jobs.ashbyhq.com/freewill/4d9d5d3f-bb67-4123-841d-90818829cb6d
- Page: https://www.1752.vc/careers/jobs/freewill-people-operations-manager-benefits-and-payroll/

## About the role

We are looking for a People Operations Manager to own the operational and compliance backbone of the FreeWill employee experience. This role is responsible for the programs and processes that make sure our people are paid accurately, enrolled in benefits, and supported through every change in their employment — from their first day to their last.

## What they're looking for

- 6+ years of benefits and payroll administration experience, including ownership of programs end to end
- Experience in a fast-paced, dynamic environment in an organization with under 500 employees
- Deep working knowledge of benefits compliance, including ACA, COBRA, ERISA/401(k), HIPAA, FMLA, and qualifying life events (QLEs)
- Experience leading annual open enrollment from planning through post-enrollment payroll reconciliation
- Strong payroll administration and reconciliation skills, with comfort handling complex, largely manual adjustments and multi-cycle changes
- Working knowledge of multistate wage & hour law and regulatory reporting, including EEO-1, plus if you’ve worked in a global working environment

Tags: People