HR Generalist

Gaggle is seeking an experienced HR Generalist to oversee key areas of our people operations, including benefits administration, payroll accuracy, HR systems, and multi-state compliance across both employees and contractors. This is a role with real ownership for someone who works independently, takes initiative, and enjoys solving problems. The ideal candidate is comfortable balancing day-to-day HR administration with process improvement and is eager to identify opportunities to make our HR operations more effective and scalable. You will have a hand in shaping how HR operates at Gaggle, while supporting a positive employee experience.

Key Responsibilities

Benefits Administration

• Own new-hire benefits enrollment and annual open enrollment administration, serving as the point of contact with our benefits broker.
• Reconcile benefit enrollment and carrier billing and resolve discrepancies with brokers, carriers, employees, and Finance.
• Troubleshoot benefit questions and exceptions as they come up, and catch discrepancies before they become employee-facing problems.
• Manage COBRA notices and continuation coverage enrollment for departing employees, coordinating with our broker and carriers.
• Manage supplemental employee engagement and perks programs.

Payroll

• Maintain a complete, audit-ready log of every payroll-impacting change (hires, terminations, compensation, benefits, leave pay, etc.) and provide it to Finance ahead of each payroll cycle (Finance owns payroll processing, funding, reconciliation, and GL booking).
• Partner with Finance to verify data accuracy before each payroll run and troubleshoot discrepancies as they come up.
• Support Finance in opening new payroll tax accounts when hiring into 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 and procedures to provide reliable backup payroll support as needed.

HR Systems & Administrative Support

• Maintain 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, and look for 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 as needed to maintain continuity across the team.

Compliance

• Manage employment compliance filings (ACA, EEO-1, Form 5500, etc.), reviewing and validating vendor-prepared filings before submission.
• Lead the annual handbook review process and Gaggle Compliance Month.
• Build and maintain our multi-state contractor classification framework, keeping an eye on higher-risk states.
• Take point on responding to any contractor classification challenges.

Employee Relations

• Serve as the primary point of contact for employee relations concerns, coaching managers through routine performance and conduct conversations and looping in HR leadership on anything complex or sensitive.
• Support workplace investigations in partnership with HR leadership, documenting findings thoroughly.
• Help managers understand and apply HR policy consistently as people issues come up.

Qualifications

Required

• 4+ years in an HR generalist or HR operations role that included benefits administration and payroll data management.
• PHR (HRCI) or SHRM-CP certification.
• Bachelor's degree in HR, business, or a related field, or equivalent practical experience.
• Hands-on experience with a full-service payroll/HRIS platform, and experience with Paychex Flex.
• Working knowledge of multi-state compliance for employee and contractor workforces.
• Comfortable building and pulling custom reports from a complex HRIS platform.

Preferred

• Experience with Flock, Breezy, or a similar HRIS/ATS platform.
• Prior experience supporting a remote or distributed team.
• Notary Public commission, or willingness to obtain one.

Core Competencies

• You work independently and take full ownership of your tasks without needing close supervision.
• You're detail-oriented, taking a “measure twice, hammer once” approach to ensure accuracy.
• You look for what needs to get done or could be improved rather than waiting to be told.
• You work through tasks quickly and consistently, rather than letting things pile up.
• You're a self-directed learner who enjoys figuring out new systems and processes.
• You care about people even when they never know what you did for them.

Salary Range and Benefits

Please apply to this posting in order to learn more about the starting salary range and benefit options. Some benefits highlights:

• We're a remote-first company; our team works together across all 50 US states
• PPO and HDHP health insurance plans through BCBS of Illinois; coverage includes treatment for fertility (including IVF) as well as offering 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 with each paycheck
• Employee Assistance Program through Paychex and Guardian (includes financial and legal assistance)
• Flexible PTO
• Generous, 100% to 70% paid leave plans, up to 90 days
• Pet Insurance Discount Program
• Fun perks such as team recognition programs, holiday gifts and bonuses, raffles, and fantasy football leagues

Our Team Commitment

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Gaggle ( is proud to be recognized as a 2023 Top Workplace ( and also a proud recipient of the 2024 Top Workplaces USA Today ( award. We are committed to equal opportunity without regard to age, race, creed, color, national origin, ancestry, marital status, affectional or sexual orientation, gender identity or expression, disability, nationality, or sex.