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People Operations Generalist

Wayground· People & Culture – People Operations
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Hybrid (New York, NY)$90k - $120kFull-timePosted 1w ago

About the role

Hands-on, individual-contributor role focused on executing core People and Legal Operations processes including onboarding, payroll, benefits, leave, contract operations, and vendor documentation. Hybrid NYC-based with in-office four days/week.

Responsibilities

  • Own HRIS as the system of record: configuration, workflows, reporting, integrations, and data integrity across the full employee lifecycle.
  • Run onboarding and offboarding: offer letters, background checks, I-9 and E-Verify, provisioning and deprovisioning, equipment, first-week experience, exit logistics.
  • Run semi-monthly US payroll end to end, including off-cycles, corrections, and reconciliation with Finance.
  • Administer benefits: open enrollment, carrier and broker management, qualifying life events, COBRA, 401(k) administration and audit support.
  • Administer all leave types across states: FMLA, state paid family and medical leave, parental leave, disability, and accommodations, including the tracking and pay coordination behind each.
  • Own People spend management: budget tracking, invoice and reimbursement approvals, headcount and benefits cost reporting alongside Finance.
  • Serve as the first point of contact for all US employee questions on pay, benefits, policy, and systems.
  • Maintain multi-state employment compliance: registrations in new states, required postings and notices, wage and hour, classification, handbook and policy updates.
  • Run contract operations end to end: intake and routing, template management, redline coordination with outside counsel, execution, storage, and renewal tracking.
  • Manage the customer legal and security review queue: DPAs, security questionnaires, insurance certificates, and documentation requests.
  • Support compliance and certification efforts as program coordinator across internal owners and auditors.
  • Work with finance on insurance renewals for the business and benefits with people.
  • Own the vendor documentation workflow in Asana: intake, required documentation, approvals, signatures
  • Collect and maintain vendor records: W-9s, COIs, security and privacy documentation, signed agreements, renewal and expiration dates.
  • Maintain the process itself: keep the Asana project structured so anyone can see where a vendor stands without asking.

Qualifications

  • 2+ years in People Operations, ideally at a startup or in a fast-moving environment.
  • US payroll, benefits, and leave administration experience across multiple states.
  • Working knowledge of multi-state US employment compliance.
  • Hands-on Rippling experience (or a comparable HRMS) across the full employee lifecycle.
  • A process mindset: you spot what's inefficient and fix it, and you document as you go.
  • Strong organization and attention to detail, comfortable owning several workstreams at once.
  • A collaborative approach: you build trust quickly and make cross-functional partners' lives easier.

Skills

Required:HRIS (system of record) managementUS payroll processingBenefits administrationLeave administration (multi-state)
Nice to have:Contract operationsVendor documentation management

Benefits

  • Healthcare coverage for you and your dependents.
  • Competitive compensation.
  • On-site presence, flexible PTO.
  • Additional health, financial, and professional development benefits.
Last updated Oct 21, 2026. Interested? Apply on the company site.

About Wayground

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Find standards-aligned resources that engage every student. Wayground (formerly Quizizz) helps teachers differentiate instruction with AI and track student progress.

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