People Operations Manager (Benefits & Payroll)

About Us
FreeWill 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 FreeWill? Check out the 2025 Best Manager Ever podcast featuring Anthony Sottile, FreeWill's VP of Partner Success on either Spotify or Apple.
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. 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.
Responsibilities
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 FreeWill'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
Process leave and PTO-related payment adjustments
Process off cycle payments, including retroactive pay/pay corrections and bonuses
HRIS Management & Employee Lifecycle:
Own responsibility for keeping our HRIS, Justworks, as our accurate source of truth on employee data - — including managing all changes, new hires, manager changes, wage rate and variable compensation changes, title changes, and all other employee data changes, terminations
Audit the HRIS system regularly to ensure data accuracy
Manage I-9 and E-Verify completion and background checks (Checkr) for new hires
Respond to requests for employment verifications
Management of our onboarding system (Ashby) + new hire checklists. Assist with scheduling company required training for employees for the first few weeks.
Manage the full offboarding process for voluntary and involuntary exits, including documentation and final-pay tasks
Manage and track severance agreements and payouts with discretion and compliance
Compliance & Regulatory Reporting:
Own EEO-1 and other regulatory filings
Manage wage & hour compliance and employment verification requests
Manage required annual trainings such as anti-harassment and anti-discrimination as required by state law
Track and stay current on federal, state, and local employment law changes relevant to our staff — FreeWill's team of nearly 200 is fully remote, working across 30+ states and 4 countries
Contractors & International Employees:
Manage the contractor and international Employer of Record (EOR) population employment life cycle end to end
Facilitate new contractor hires and track contract renewal reminders, maintaining a contractor roster
Manage the employee lifecycle for international staff, including work through Deel and Justworks EOR, ensuring compliance
Other Tasks and Special Projects:
Monitor company’s digital mailbox (which contains mostly state and labor related mailings), forward all other mailings to relevant departments within FreeWill
Owning documentation and updating of HR processes, training coverage and backup as needed
Take on operational, compliance, and systems initiatives across the People & Culture function as the team and company grow (e.g., task management for annual 360 and annual review processes)
Required Skills And Experience
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
Vendor and broker management experience, including plan negotiations and analysis
Experience administering involuntary exits and severance with discretion and compliance
Experience working in an HRIS and/or PEO, ensuring data and systems are accurate and up to date
Strong project management and execution skills, with the ability to run multiple recurring processes at once
Laser-focused attention to detail and a high bar for data accuracy
A highly adaptable, empathetic individual who enjoys working in a fast-moving, ever-changing environment
Alignment with FreeWill values of kindness, focus, joy, and courage
Hiring Process
Hiring Manager Interview (30 minutes)
Take Home Assignment (1 hour; on your own time)
Panel interview (30 minutes)
Final interview with leadership
Offer (contingent on positive references)
Please note that steps in the hiring process can and may change and the Recruiter will be your point of contact in sharing about any updates in terms of the process. If you are selected to move forward in this process, the Recruiter will share more details about the hiring process and interviewers. However, this is a good estimate of what you can expect. For most roles, our hiring processes take an average of 4 weeks.
AI Policy
We are excited to engage with candidates who can demonstrate their experience and skills through their own words and work, not through AI-generated content. We want to understand your genuine interest in the company and your unique perspectives, not simply AI-driven responses. We ask that you refrain from use of AI-generated content during the hiring process which includes phone screens, video interviews, tech screens, or other assessment stages except as otherwise indicated to you by the Recruiter.
For example: Using ChatGPT to generate scripted answers to application questions or during phone screens and video interviews is strongly discouraged and will result in not moving forward in the hiring process. However, the use of an AI design tool to enhance the design of a presentation deck is permitted.
The Recruiter will be able to provide additional guidance during the hiring process if needed. If hired at FreeWill, we do encourage the use of AI in your role to build upon or enhance your skill set.
AI use by FreeWill: Our hiring process may include the use of AI- assisted tools for interview transcription, eva

Work arrangement
Yes