People Operations Manager

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 ensure 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 ensuring compliance is 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.

• 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 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.

• Contractors & International Employees:

  • Manage the contractor and international Employer of Record (EOR) population employment lifecycle 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, forward all other mailings to relevant departments within FreeWill.
  • Own 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.

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.