Lead Counsel, HR Products, Insurance & Benefits

Lead Counsel, HR Products, Insurance & Benefits Rippling gives businesses one place to run HR, IT, and Finance. It brings together all of the workforce systems that are normally scattered across a company, like payroll, expenses, benefits, and computers. For the first time ever, you can manage and automate every part of the employee lifecycle in a single system. About This Position We are looking for a highly‑motivated, business‑minded attorney to join as Lead Counsel, HR Products, Benefits & Insurance on the Legal & Compliance team. In this role you will partner closely with Product, Sales and Compliance and report to the Deputy General Counsel, Products Legal. Your primary responsibility will be to provide key legal guidance on a wide range of insurance and benefits initiatives, including product counseling for our Insurance, Benefits, PEO, and EOR teams and regulatory matters such as ERISA, COBRA and Section 125 cafeteria plan rules. You will build a world‑class product counsel function at a rapidly growing company and use AI tools to automate legal workflows and enable self‑service resources for our cross‑functional partners. You Will Serve as the primary legal advisor for Rippling’s Benefits Administration, Insurance, PEO, and EOR product teams on U.S. and international insurance and benefits regulatory matters, including ERISA, COBRA, and Section 125 cafeteria plan rules. Guide Rippling’s insurance licensing program. Review and advise on vendor and partnership arrangements involving insurance or benefits products. Manage Rippling’s corporate insurance program. Partner with our Product, Operations, Business Development, Sales and Client Services teams to build and manage Rippling’s product counseling function. Navigate complex regulatory frameworks in the U.S. and abroad to create scalable and innovative solutions for our products and services. Drive the compliance culture at Rippling and embed integrity and compliance in all of the company’s operations as it grows. Advise and assist with general legal needs as they arise. Build and deploy AI‑powered tools to automate legal workflows, scale the team’s output, and enable self‑service resources for Legal’s cross‑functional partners. You Have 5+ years of legal experience in a regulated space, with strong preference for experience with ERISA‑governed employee benefits, COBRA and insurance regulatory law. 2+ years in an in‑house product counseling role. Strong interest in and experience advising on legal issues in highly regulated industries. Experience leading and advising teams across different global regions. Passion for navigating complex regulatory frameworks and finding solutions. Law degree (e.g., JD or equivalent). Entrepreneurial mindset, solution‑oriented ethos, and readiness to roll up your sleeves. Comfort experimenting with and building on top of AI tools. Strong project management and organizational skills. Excellent drafting and written and verbal communication skills with the ability to break down complex legal jargon into easy‑to‑understand and practical advice. Strong analytical and problem‑solving skills. Sense of humor. Additional Information Rippling is an equal opportunity employer and is committed to building a diverse and inclusive workforce. We do not discriminate based on race, religion, color, national origin, ancestry, physical disability, mental disability, medical condition, gender identity or expression, age, sexual orientation, veteran or military status, or any other legally protected characteristic. Rippling provides reasonable accommodations for candidates with disabilities who need assistance during the hiring process; please email View email address on click.appcast.io to request an accommodation. Rippling highly values employees working in‑office to foster collaboration and company culture. For office‑based employees who live within the defined radius of a Rippling office, working in the office at least three days a week is considered an essential function of the role. This role will receive a competitive salary, benefits, and equity. Pay range: 177,000 – 295,000 USD per year for US‑based employees. #J-18808-Ljbffr Rippling