United States Remote (Global) Contract

Gaggle is hiring a HR Generalist

Responsibilities

  • Manage new-hire benefits enrollment and annual open enrollment, acting as the primary contact with the benefits broker.
  • Reconcile benefit enrollment data and carrier billing, resolving discrepancies with brokers, carriers, employees, and Finance.
  • Address benefit questions and exceptions, catching discrepancies before they affect employees.
  • Administer COBRA notices and continuation coverage for departing employees, coordinating with the broker and carriers.
  • Oversee supplemental employee engagement and perks programs.
  • Maintain a complete, audit-ready log of all payroll-impacting changes and provide it to Finance before each payroll cycle.
  • Collaborate with Finance to verify data accuracy before payroll runs and resolve discrepancies.
  • Assist Finance in opening new payroll tax accounts when hiring in a new state.
  • Maintain compensation reporting tools to support salary and job title analysis, flagging pay equity concerns for HR leadership.
  • Cross-train in payroll processing to provide reliable backup support as needed.
  • Keep accurate, audit-ready employee and personnel data across Paychex, Flock, Breezy, and related systems.
  • Serve as the internal point of contact for employee questions on HR systems and support ATS administration.
  • Build and run custom reports in Paychex, seeking ways to optimize HR processes.
  • Keep relevant HR playbooks and documentation current.
  • Oversee annual performance reviews and workforce surveys.
  • Help transition and train new HR team members as needed.
  • Cross-train on core processes to maintain team continuity.
  • Manage employment compliance filings, reviewing and validating vendor-prepared submissions before filing.
  • Lead the annual handbook review process and Compliance Month.
  • Build and maintain a multi-state contractor classification framework, focusing on higher-risk states.
  • Take the lead on responding to contractor classification challenges.
  • Serve as the primary contact for employee relations, coaching managers on routine performance and conduct issues and escalating complex matters to HR leadership.
  • Support workplace investigations in partnership with HR leadership, documenting findings thoroughly.
  • Help managers understand and apply HR policy consistently as issues arise.

Benefits

  • PPO and HDHP health insurance plans through BCBS of Illinois, covering fertility treatment including IVF, virtual visits, and mental health resources.
  • Dental insurance including orthodontia through Guardian.
  • Vision insurance through BCBS/EyeMed.
  • HSA, FSA, LPFSA, and DCFSA available, with a $500 annual company contribution.
  • 401(k) plan with immediate vesting and a 4% company contribution per paycheck.
  • Employee Assistance Program through Paychex and Guardian, including financial and legal assistance.
  • Flexible PTO.
  • Generous paid leave plans, 100% to 70% pay, up to 90 days.
  • Pet Insurance Discount Program.
  • Fun perks such as team recognition programs, holiday gifts and bonuses, raffles, and fantasy football leagues.

Work Arrangement

Remote (Worldwide) — United States

Job Details
Location United States
Work mode Remote (Global)
Employment Contract
Department Human Resources
Category other
Posted 20 days ago
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About company
Gaggle logo

Gaggle is the premiere student safety software enabling K-12 schools to monitor student activity on school-provided devices for concerning content. Our mission is to ensure the safety and well-being of students and schools by leveraging people and technology.

We provide solutions that help K-12 districts protect student safety and mental well-being through technology and 24/7/365 U.S.-based human support. Our services include safety management, therapy, web filtering, archiving, and more.

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