People Operations Generalist

Responsibilities

• Own day-to-day benefits administration across the full vendor stack, including enrollments, terminations, and qualifying life events.
• Manage the end-to-end open enrollment process, including vendor coordination, employee communications, and system updates.
• Administer leave programs independently, including FMLA, Massachusetts PFML, and ADA accommodations.
• Maintain data integrity within Rippling to ensure accurate and audit-ready people records.
• Oversee compliance obligations such as I-9/E-Verify completion and MA Unemployment fact-finding.
• Identify opportunities to automate manual processes and build more efficient People Ops workflows.

Requirements

• 2-4 years of HR or people operations experience with direct, hands-on ownership of benefits and leave administration.
• Proven experience independently administering MA PFML and a strong understanding of federal leave programs.
• Experience managing end-to-end open enrollment and managing vendor relationships.
• Proficiency with HRIS platforms, specifically Rippling.
• A proactive, ownership-driven mindset with the ability to build processes from scratch.
• Interest in using AI and automation to improve operational efficiency.

Benefits

• Medical, Dental, and Vision insurance (BCBS and EyeMed).
• 401(k) with up to 3% company match.
• Paid Parental Leave (100% covered).
• Incentive Stock Options.
• Flexible vacation policy and 12 company holidays.
• Professional Development & AI Tools Stipend.
• In-Office Commuter Stipend.

About the Company

Robin is reimagining workplace operations as a strategic function, using AI to help workplace teams automate logistics and simplify operations. Our platform is used by thousands of offices worldwide to bring order to the chaos of office management. We work in a hybrid model, meeting in person at our Boston HQ two days a week.