About PeopleOps Jobs We started PeopleOps Jobs (https://peopleopsjobs.io) to help companies that care about HR find the right people in the HR and People Operations world. -- About the role The position is at an insurtech company. We are seeking an organized, detail-oriented People Operations and Compliance Generalist to join our team. In this position, you will maintain the seamless operation of our people operations and compliance functions. You will serve as the primary resource for benefits and administrative inquiries while ensuring payroll compliance mandates and state reporting are completed accurately and on time. You will collaborate closely with external benefits brokers, payroll providers, insurance carriers, compliance vendors, and government agencies to optimize operational efficiency and deliver an exceptional employee experience. This role is ideal for a professional who takes pride in precision, manages sensitive data with total discretion, and proactively identifies opportunities to automate routine tasks. You will operate independently while partnering effectively with internal colleagues and external stakeholders.

Responsibilities

Be the go-to for benefits questions. Provide employees with timely, accurate guidance regarding health, dental, vision, retirement, and supplemental benefit offerings. Coordinate enrollments, qualifying life event updates, Betterment 401(k) plans, COBRA, and annual open enrollment. Act as the initial point of contact for all workforce benefits inquiries. Partner with our benefits broker. Serve as the primary liaison with Sequoia, our benefits broker. Collaborate with Sequoia to administer plan offerings and maintain full compliance with Federal, state, and local regulations, including ACA filings, non-discrimination testing, and mandatory disclosures. Keep payroll compliance and state compliance airtight. Monitor and enforce compliance with state and local employment standards, including state withholding and unemployment account registrations, account maintenance, paid leave and disability programs, workers' compensation coverage, and timely responses to agency notices. Own AbstractOps, CT Corp, and the mailroom. Manage AbstractOps (our multi-state business compliance tool), including reviewing digital notices and physical mail forwarded by Executive Assistants. Oversee incoming corporate mail, route correspondence, and handle standard inquiries. Manage the relationship with CT Corporation, our registered agent across all operating states. Run core people processes in Rippling (our HRIS). Direct HRIS record updates, benefits administration, and leave management (FMLA, parental leave, etc.), ensuring all data modifications are recorded accurately in Rippling. Keep the paper trail audit-ready. Facilitate compliance audits by compiling required documentation and maintaining well-structured records. Preserve accurate files, mandatory postings, and legal records to mitigate operational and compliance risk. Own the handbook, policies, and employee communications. Maintain and update the employee handbook and organizational policies to reflect current legal requirements. Draft and distribute internal communications regarding benefits and policy updates. Make Lattice our home for employee documentation. Oversee Lattice administration, train staff on system navigation, monitor and ensure regular 1:1 documentation between managers and direct reports, and assist in managing company-wide performance review cycles. Guide employees on maximizing tool functionality, including Slack integrations, the AI 1:1 assistant, and the Claude MCP connection. Turn people data into useful reporting. Generate accurate reports tracking real-time headcount, turnover metrics, and hiring trends. Automate the repeatable. Partner with the IT department to configure auto-responses and workflows for common inquiries regarding benefits, PTO, and policy guidelines using Console or equivalent ITSM tools. The goal is to provide immediate, reliable answers outside standard business hours while freeing up time for high-impact initiatives. Please note: This list of duties and responsibilities is not exhaustive. Ad hoc requests and additional tasks may come up as the role evolves.

Qualifications

Bachelor’s degree preferred; equivalent practical experience will be evaluated. 2–5 years of background in benefits administration and multi-state payroll tax compliance. Strong understanding of benefits administration and employment law compliance. Prior experience with Rippling (our HRIS and payroll platform) is preferred.

Benefits

Competitive Compensation: Competitive salary and equity packages for all employees Healthcare Plan: Platinum medical, dental, and vision Free life insurance: Including long-term disability & short-term disability Unlimited PTO: Uncapped vacation days & paid holidays Family Leave: Maternity & paternity 401(k) Contribution: We contribute 3% of your income, even if you don't contribute WFH Benefits: Lunch on us 2x/week, monthly phone stipend & other home office perks Health FSAs & HSAs: Pre-tax accounts for out-of-pocket medical expenses Team events & Offsites: We're remote, but we regularly get together Pay: $110k to $140k annually.