People Operations Manager Payroll

About Us

Free Will is an award-winning, social-good startup that has partnered with 2,400+ nonprofits who support our mission while generating $14B in gift commitments for nonprofits since we were founded in 2017. We’ve been featured in the New York Times, Forbes, Oprah’s magazine, and our co-CEOs have even been named to Town & Country’s “Top 50 Philanthropists” list.

All of this is because we’ve figured out how to make some powerful (but complicated!) ways to donate much easier and more accessible. Our products make things easier for the donors who want to change the world and for nonprofits doing heroic work around the planet. We partner with nonprofits of all sizes to diversify fundraising across individual and institutional giving, from legacy gifts and tax-smart donations to foundation, corporate, and government grants.

In the last 9 years, we’ve grown from 5 people to 200+ (all smart, tenacious, and kind), and continue to grow. We’d love to have you be a part of this adventure. We were named a "Most Loved Workplace" by both Newsweek and Best Practice Institute and the 2025 Most Loved Workplaces® for Diversity by the Best Practice Institute. In 2026, we were named as one of Forbes' Best Startup Employers.

Curious about company culture and management at Free Will? Check out the 2025 Best Manager Ever podcast featuring Anthony Sottile, Free Will's VP of Partner Success on either Spotify or Apple.

We are looking for a People Operations Manager to own the operational and compliance backbone of the Free Will 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. It spans benefits administration, payroll, compliance and regulatory reporting, contractor and Employer of Record (EOR) management, and the full onboarding and offboarding lifecycle.

This is a high-ownership, detail-critical role for someone who takes pride in getting the numbers right and the compliance airtight. You'll own our relationship with our benefits broker and vendors, partner closely with Finance, and be the trusted go-to for employee questions about pay and benefits.

This role reports directly to our People and Culture Lead.

This is a full-time remote position. The offers for this role will be in the range of $95,000-$105,000 per year and includes full benefits and equity.

• Collaborating with other members of the People team (Recruitment, HR), Finance, and other departments on joint projects and where applicable

• Benefits Administration:

  • Serve as the first point of contact for employee benefits questions

  • Coordinate with Justworks for international benefits questions

  • Lead annual open enrollment end-to-end, from planning through post-open enrollment benefits administration

  • Partner with our insurance broker on health insurance renewals, including plan negotiations, plan cost analysis, claim spending analysis through a level-funded insurance plan

  • Manage FSA/HSA spend-account benefits, including monthly funding and invoicing

  • Facilitate qualifying life events (QLEs) enrollment

  • Partner with our third-party COBRA administrator for all employee exits

  • Own annual ACA filing and compliance, 401(k) compliance, and monthly benefits reporting

  • Keep employee-facing benefits resources current on Free Will's employee intranet

  • Collect employee feedback on benefit offerings and propose improvements to total benefits packages including perk benefits

• Payroll Administration:

  • Partnering with the finance team where applicable

  • Manage employee deductions and payroll modifications within our PEO

  • Run payroll reconciliation semi-monthly to verify accuracy

  • Pro…