People Operations Generalist

People Operations Generalist – Full Time, Hybrid, Boston, Massachusetts, United States. The annual base salary ranges from USD 100,000 to 140,000. About Robin Robin is reimagining workplace operations as a strategic function, and AI is at the core of how we get there. We help workplace teams bring order to the chaos by automating logistics, simplifying operations, and giving employees a seamless way to connect with the office. Today, our workplace operations platform is used by thousands of offices around the world. We believe the best connections and ideas come from being in the room together, so we work in person two days a week on Tuesdays and Thursdays at our Boston HQ. But we also build flexibility into every part of our product and culture, so people can do great work without burning out. About the Role Our People team is small by design, and we hire people who are energized by that. We need someone who can own benefits and leave administration independently from day one—then grow into whatever interests them most from there. You'll have real ownership over compliance, vendor relationships, and people data at a company that moves fast and doesn’t over‑segment responsibilities. If you’ve been waiting for a role where you have the chance to actually run something, this is it. What you’ll do Own day‑to‑day benefits administration across our full vendor stack—enrollments, terminations, qualifying life events, etc. across BCBS, EyeMed, Reliance Matrix, and Principal. Run open enrollment end‑to‑end: vendor coordination, employee communications, and system updates in partnership with our benefits brokers. Administer leave programs independently—FMLA, Massachusetts PFML, ADA accommodations, etc—and support employees through the full leave lifecycle. Maintain data integrity in our HRIS (Rippling) and ensure our people records are accurate and audit‑ready across systems that don’t always talk to each other. Own compliance obligations (I-9 and E‑Verify completion, MA Unemployment fact‑finding, etc). Identify and fix what’s manual and repetitive—you’ll have room to build better processes, not just execute existing ones. You’ll thrive in this role if You have 2‑4 years of HR or people operations experience with direct, hands‑on ownership of benefits and leave administration—not adjacent to it, but actually running it. You’ve administered MA PFML independently and know federal leave programs well enough to handle them without a playbook. You don’t want to be handed a to‑do list. You make the list yourself, and then want to finish everything on it. You're genuinely curious about technology and think proactively about how AI and automation can make People Ops work better. You’ve managed open enrollment end‑to‑end, including vendor relationships, and you know how to audit across disconnected systems for human error. Core Competencies for Success Learning Velocity: You learn fast, stay current on employment law and HR best practices, and apply new ideas quickly. AI Proficiency: You bridge problem‑solving and operations, using AI and automation to deliver People Ops work with more accuracy and less manual lift. Ownership: You don’t wait to be told what needs to happen and when. You track it, build the process, and execute. Collaboration: You’re the kind of person employees trust to ask a “dumb question” and you take that seriously. Benefits that have your back (and your future) Medical & Dental Insurance through Blue Cross Blue Shield covered at 80% for you and your dependents, with two plan options including a High Deductible Plan with a company‑funded HSA. Vision Insurance – EyeMed coverage to keep your future in focus. Company‑paid protection – Short & Long Term Disability, Life, and AD&D insurance. Paid Parental Leave – 100% covered so you can focus on your growing family. Incentive Stock Options – Own a piece of what you’re building. 401(k) with company match – Up to 3% match to help grow your nest egg. Flexible vacation policy – Take the time you need (and yes, we actually do!). 12 company holidays – Plus your flexible time off for the perfect work‑life balance. Professional Development & AI Tools Stipend. Referral Bonus Program. Recognition perks. In‑Office Commuter Stipend. Compensation Philosophy Base salary: $110,000 – $140,000, depending on experience. Our compensation decisions are based on an individual’s experience, skills and education in line with our internal compensation philosophy. We Celebrate Diversity Robin is committed to creating a workplace that reflects the world around us. We believe that the key to good work is empowering our people and we know that diversity and inclusion are a large part of this equation. Our realities shape our everyday experiences and it’s our responsibility to our employees, our customers and our communities to address the issues with workplace representation. Robin does not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. #J-18808-Ljbffr