{"id":1256677,"url":"https://alion.io/job/freewill-people-operations-manager-benefits-payroll","title":"People Operations Manager (Benefits & Payroll)","company":{"id":1753239,"name":"FreeWill","domain":"freewill.com","url":"https://alion.io/company/freewill-com","size_band":"51-200","is_staffing_agency":false,"employer_type":"direct","is_intermediary":false,"listed_via":null,"ats_vendor":"Ashby","truth_index":null},"role":"Management","role_family":"Management","seniority":null,"employment_type":"full_time","work_mode":"remote","remote_scope":"stated_countries","remote_scope_basis":"board_field","remote_working_hours":null,"hiring_geo_confidence":"structured","locations":[],"countries":[],"hiring_countries":["US"],"hiring_countries_total":1,"salary":{"min":95000,"max":105000,"currency":"USD","period":"year","gross":null,"usd_annual":105000},"salary_estimate":null,"experience_years_min":null,"visa_sponsorship":false,"relocation_package":false,"has_equity":true,"technologies":[{"name":"ChatGPT","optional":false},{"name":"Claude","optional":false},{"name":"HIPAA","optional":false},{"name":"Wi-Fi","optional":false}],"status":"closed","first_seen_at":"2026-09-21T22:20:04Z","employer_posted_date":"2026-09-21","last_verified_at":"2026-10-14T19:43:48Z","board_verified":false,"closed_at":"2026-10-14T19:43:48Z","days_open":22,"trust":{"level":"not_scored","repost_count":null,"flags":[],"days_open":22},"description":"About Us\nFreeWill 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.\nAll 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.\nIn 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 the2025 Most Loved Workplaces® for Diversity by the Best Practice Institute. In 2026, we were named as one of Forbes' Best Startup Employers.\nCurious 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.\nAbout the role\nWe 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.\nThis 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.\nThis role reports directly to our People and Culture Lead.\nThis 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.\nResponsibilities\nCollaborating with other members of the People team (Recruitment, HR), Finance, and other departments on joint projects and where applicable\n\nBenefits Administration:\nServe as the first point of contact for employee benefits questions\n\nCoordinate with Justworks for international benefits questions\n\nLead annual open enrollment end-to-end, from planning through post-open enrollment benefits administration\n\nPartner with our insurance broker on health insurance renewals, including plan negotiations, plan cost analysis, claim spending analysis through a level-funded insurance plan\n\nManage FSA/HSA spend-account benefits, including monthly funding and invoicing\n\nFacilitate qualifying life events (QLEs) enrollment\n\nPartner with our third-party COBRA administrator for all employee exits\n\nOwn annual ACA filing and compliance, 401(k) compliance, and monthly benefits reporting\n\nKeep employee-facing benefits resources current on FreeWill's employee intranet\n\nCollect employee feedback on benefit offerings and propose improvements to total benefits packages including perk benefits\n\nPayroll Administration:\nPartnering with the finance team where applicable\n\nManage employee deductions and payroll modifications within our PEO\n\nRun payroll reconciliation semi-monthly to verify accuracy\n\nProcess leave and PTO-related payment adjustments\n\nProcess off cycle payments, including retroactive pay/pay corrections and bonuses\n\nHRIS Management & Employee Lifecycle:\nOwn 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\n\nAudit the HRIS system regularly to ensure data accuracy\n\nManage I-9 and E-Verify completion and background checks (Checkr) for new hires\n\nRespond to requests for employment verifications\n\nManagement of our onboarding system (Ashby) + new hire checklists. Assist with scheduling company required training for employees for the first few weeks.\n\nManage the full offboarding process for voluntary and involuntary exits, including documentation and final-pay tasks\n\nManage and track severance agreements and payouts with discretion and compliance\n\nCompliance & Regulatory Reporting:\nOwn EEO-1 and other regulatory filings\n\nManage wage & hour compliance and employment verification requests\n\nManage required annual trainings such as anti-harassment and anti-discrimination as required by state law\n\nTrack 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\n\nContractors & International Employees:\nManage the contractor and international Employer of Record (EOR) population employment life cycle end to end\n\nFacilitate new contractor hires and track contract renewal reminders, maintaining a contractor roster\n\nManage the employee lifecycle for international staff, including work through Deel and Justworks EOR, ensuring compliance\n\nOther Tasks and Special Projects:\nMonitor company’s digital mailbox (which contains mostly state and labor related mailings), forward all other mailings to relevant departments within FreeWill\n\nOwning documentation and updating of HR processes, training coverage and backup as needed\n\nTake 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)\n\nRequired Skills and Experience\n6+ years of benefits and payroll administration experience, including ownership of programs end to end\n\nExperience in a fast-paced, dynamic environment in an organization with under 500 employees\n\nDeep working knowledge of benefits compliance, including ACA, COBRA, ERISA/401(k), HIPAA, FMLA, and qualifying life events (QLEs)\n\nExperience leading annual open enrollment from planning through post-enrollment payroll reconciliation\n\nStrong payroll administration and reconciliation skills, with comfort handling complex, largely manual adjustments and multi-cycle changes\n\nWorking knowledge of multistate wage & hour law and regulatory reporting, including EEO-1, plus if you’ve worked in a global working environment\n\nVendor and broker management experience, including plan negotiations and analysis\n\nExperience administering involuntary exits and severance with discretion and compliance\n\nExperience working in an HRIS and/or PEO, ensuring data and systems are accurate and up to date\n\nStrong project management and execution skills, with the ability to run multiple recurring processes at once\n\nLaser-focused attention to detail and a high bar for data accuracy\n\nA highly adaptable, empathetic individual who enjoys working in a fast-moving, ever-changing environment\n\nAlignment with FreeWill values of kindness, focus, joy, and courage\n\nBenefits\nIn 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:\nWork from home\n\nFlexible 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\n\nFlexible hours\n\nCompetitive salary\n\nCommuter benefits\n\nCompany stock options\n\n401k\n\nMedical/Dental/Vision (some single coverage medical plans are 100% employer paid, subsidized rates for spousal, parent-child, and family coverage)\n\nShort-term and long-term disability insurance\n\nLife and AD&D insurance\n\nFree One Medical membership\n\nPaid parental leave for all parents\n\nPerks\nRegular (virtual) team events\n\n$250 monthly co-working budget which can be used for local co-working spaces and your home wifi bill\n\n$300 annual budget to outfit your home office or cover utility bills\n\n$1,000 referral bonuses for growing our FreeWill community\n\n$800 annual professional development budget\n\nClaude (AI Assistant) company/team account\n\nHiring Process\nHiring Manager Interview (30 minutes)\n\nTake Home Assignment (1 hour; on your own time)\n\nPanel interview (30 minutes)\n\nFinal interview with leadership\n\nOffer (contingent on positive references)\n\nPlease 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.\nAI Policy\nWe 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.\nFor 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.\nThe 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.\nAI 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.\nEEOC & Diversity Statement\nFreeWill 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.\nWe 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.\nDon’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. 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