Lead Counsel, HR Products, Insurance & Benefits

About Rippling 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. Take onboarding, for example. With Rippling, you can hire a new employee anywhere in the world and set up their payroll, corporate card, computer, benefits, and even third-party apps like Slack and Microsoft 365—all within 90 seconds. Based in San Francisco, CA, Rippling has raised $1.4B+ from the world’s top investors—including Kleiner Perkins, Founders Fund, Sequoia, Greenoaks, and Bedrock—and was named one of America's best startup employers by Forbes. We prioritize candidate safety. Please be aware that all official communication will only be sent from @ Rippling.com addresses. 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 will report to our Deputy General Counsel, Products Legal. You will provide key legal guidance to our business team on a wide range of insurance and benefits related initiatives. This will include providing product counseling for our Insurance, Benefits, PEO, and EOR teams, with a focus on insurance and benefits regulatory issues. You are a self-starter and are excited to learn about new products and new areas of law. You are a strategic thinker and want to build a world-class, highly efficient product counsel function at a rapidly growing company. You have a passion for providing creative, proactive, and pragmatic legal guidance. 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 our operations as our company grows. Advise and assist with Rippling’s 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 ready 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. We are committed to building a diverse and inclusive workforce and do not discriminate based on race, religion, color, national origin, anc