People Operations Manager (Benefits & Payroll)

At FreeWill, a Most Loved Workplace® certified employer in the Internet/E-Commerce space.

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 Benefits In addition to the immense personal and professional satisfaction you’ll gain from helping to raise $1T for high impact nonprofits in a kind and joyful work environment, full time employees at FreeWill are eligible for the following benefits: Work from home Flexible Paid Time Off policy. We trust staff to manage their own schedules and take the time off you need to be your best, as long as your work is on track. We recommend staff take a minimum of three weeks annually Flexible hours Competitive salary Commuter benefits FreeWill stock options 401k Medical/Dental/Vision (some single coverage medical plans are 100% employer paid, subsidized rates for spousal, parent-child, and family coverage) Short-term and long-term disability insurance Life and AD&D insurance Free One Medical membership Paid parental leave for all parents Perks Regular (virtual) team events $250 monthly co-working budget which can be used for local co-working spaces and your home wifi bill $300 annual budget to outfit your home office or cover utility bills $1,000 referral bonuses for growing our FreeWill community $800 annual professional development budget Claude (AI Assistant) company/team account 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 FreeWill 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, evaluation, or fraud detection. Human oversight and decision making is maintained throughout the hiring process and for all final hiring decisions. This processing is conducted in compliance with applicable Data Protection, AI Governance, and Labor Laws. EEOC & Diversity Statement FreeWill is an equal opportunity employer and we value diversity. We are committed to finding talent that is not determined on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by law. We are a remote-first company with employees in the US, Brazil, Canada, and Pakistan. In the US, we are able to hire in 47 states and D.C. Unfortunately, we are unable to hire in Colorado, Alabama, or Louisiana at this time. We also can’t sponsor working visas, so all applicants will need to have work authorization in their respective country. Don’t check off every box in the requirements listed above? Please apply anyway! Studies have shown that marginalized communities - such as women, LGBTQ+ and people of color - are less likely to apply to jobs unless they meet every single qualification. FreeWill is dedicated to building an inclusive, diverse, equitable, and accessible workplace that fosters a sense of belonging – so if you’re excited about this role but your past experience doesn’t align perfectly with every qualification in the job description, we encourage you to still consider submitting an application. You may be just the right candidate for this role or another one of our openings!

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