People Operations and Compliance Generalist

Assured is on a mission to modernize insurance. Claims processing (i.e. should we pay this claim?), while often overlooked, is the foundation of the entire industry. It’s currently highly manual, involving phone calls, faxes, and gut instinct, costing tens of billions of dollars a year. We can do better. At Assured, we provide large insurers with the software solutions they need to win in a modern, technology-driven world. From self-service claim-filing software to backend fraud detection, we’re the engine that powers claims processing for some of the largest insurers in the world. The challenges we face are deep and diverse, from creating digital experiences that provide comfort and clarity to claimants at their most stressed and vulnerable to orchestrating large-scale ML-driven decision-making on billions of dollars of claims payments, life at Assured is dynamic, collaborative, and rewarding. We're looking for an organized, detail-oriented People Operations and Compliance Generalist to join our team. In this role, you'll keep the administration and compliance of our people operations function running smoothly. You'll be the go-to person for benefits and administrative questions, and you'll make sure payroll compliance requirements and state filings are completed accurately and on time. You'll work closely with our external benefits broker, payroll provider, insurance companies, payroll compliance vendors, and government agencies to keep operations efficient and give every teammate a great employee experience. This is a role for someone who takes pride in getting the details right, handles sensitive information with discretion, and looks for ways to automate the repetitive parts of the job. You'll work independently while partnering with teammates and outside partners across the business. SOME OF THE WORK YOU'LL OWN: 💬 Be the go-to for benefits questions. Give employees timely, accurate answers on health, dental, vision, retirement, and other benefit programs. Coordinate enrollments, life event changes, 401(k) plans through Betterment, COBRA, and annual open enrollment. Be the starting point for all benefits questions from employees. 🤝 Partner with our benefits broker. Serve as the primary point of contact for Sequoia, our benefits broker. Work with Sequoia to administer benefit plans and ensure Assured is compliant with all Federal, state and local benefits-related regulations including ACA filings, non-discrimination testing and any required notices. 🏛️ Keep payroll compliance and state compliance airtight. Monitor and maintain compliance with state and local employment requirements including state withholding and unemployment registrations, state and local account maintenance, paid family leave and disability programs, keeping our workers compensation up to date, and responding to all notices from states and local jurisdictions. 📬 Own AbstractOps, CT Corp, and the mailroom. Own AbstractOps (our multi-state business compliance tool) including reviewing mail received in AbstractOps and mail forwarded from our Executive Assistant(s). Manage incoming company mail, distribute correspondence, and respond to routine inquiries. Own relationship with CT Corporation, our registered agent in all the states where we operate. 🗂️ Run core people processes in Rippling (Assured’s HRIS). Own HRIS updates, benefits administration, and leave coordination (FMLA, parental etc.), and enter all changes in Rippling. 🧾 Keep the paper trail audit-ready. Support audits by gathering requested documentation and keeping records organized. Maintain proper documentation, required notices, and records for legal purposes to reduce compliance and operational risk. 📘 Own the handbook, policies, and employee communications. Manage and update the employee handbook and company policies, keeping them current and compliant. Distribute employee communications on benefits and policy updates. 🌱 Make Lattice our home for employee documentation. Administer lattice, train employees on using it, check and follow-up with managers that regular 1:1s are happening and documented across the org, and help administer annual reviews (once an all-company review cycle is in place). Show employees how to get the most out of the tool, including the Slack integration, the AI agent in 1:1s, and the MCP connection with Claude. 📊 Turn people data into useful reporting. Produce up-to-date headcount, turnover, and hiring reports. ⚙️ Automate the repeatable. Work with the IT department to set up auto-replies and playbooks to answer common employee questions on benefits, PTO, and other employee handbook topics (using Console or another ITSM vendor). The goal is for employees to get a fast, correct answer, even outside business hours, and for you to get time back for higher-value work. Please note: This list of duties and responsibilities is not exhaustive. Ad hoc requests and additional tasks may come up as the role evolves. HOW YOU'LL MAKE AN IMPACT: 🛡️ Keep Assured compliant and audit-ready. Accurate filings, current notices, and well-organized records reduce risk and make audits straightforward. ⚡ Use automation and AI to move faster. Set up auto-replies for common questions and help the team get more out of Lattice's AI features, so repetitive work doesn't take over the week. 📈 Build a foundation that scales. Documented processes, clean systems of record, and reliable reporting give People Ops a base that holds up as Assured grows. 😊 Give every teammate a great employee experience. Clear, accurate, and timely answers on benefits and policies mean people can spend their energy on their work instead of chasing down HR questions. WHAT YOU'LL BRING: 🎓 Bachelor’s degree preferred; equivalent work experience will be considered. 🗓️ 2–5 years of experience in benefits administration and multi-state payroll tax compliance. 📋 Knowledge of benefits administration and employment compliance. 💻 Experience with Rippling (Assured’s HRIS and payroll systems) is preferred. YOU'LL PROBABLY THRIVE HERE IF YOU: 🔍 Have an exceptional eye for detail. You're strongly organized, and you catch the small stuff before it becomes a filing error or an audit finding. ⏱️ Juggle priorities and meet deadlines. You can keep several workstreams moving at once and hit the deadlines that payroll and compliance don't move. ✍️ Communicate clearly. You have excellent verbal and written communication skills and can explain benefits and policy updates in plain language. 🙋 Lead with service. You bring a strong customer service orientation and interpersonal skills, and you treat every teammate question as worth a real answer. 🔒 Handle sensitive information with discretion. Confidentiality is second nature to you. 🧭 Work independently and collaborate well. You can run with your own work while partnering effectively with internal teams and external partners. 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: Assured contributes 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 **We have been made aware of individuals falsely posing as recruiters from Assured Insurance Technologies Inc. Please note that we only contact candidates from official @assured.claims http://assured.claims email addresses and all interviews are conducted through verified company channels. If you are unsure whether a message is legitimate, please contact us directly at recruiting-ops@assured.claims before sharing any personal information** Our Commitment: We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, sex, gender, gender expression, sexual orientation, age, marital status, veteran status, or disability status. We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, perform essential job functions, and receive other benefits and privileges of employment. Please contact us to request accommodation.