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.

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.

• 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…