PEO Benefits Operations Manager

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. About the role Rippling PEO co-employs tens of thousands of worksite employees, and many of our clients join Rippling PEO for its top-notch benefits offerings. As that business scales, so does the complexity of operating it—and the stakes of getting it right. This is a project management role at the center of two of PEO's highest-visibility operational programs: the annual benefits renewal and the mid-year risk management motion. You’ll own these programs end-to-end. That means defining workstreams, driving cross-functional accountability across teams you don't directly manage, surfacing risks proactively, and ensuring on-time delivery across a large, complex stakeholder map that spans Product, Engineering, Account Management, carriers, and brokers. If you're someone who thrives on building operational structure where it doesn't fully exist, managing high-stakes programs in ambiguous environments, and making a measurable impact on financial outcomes—this role is for you. What you will do Lead the end-to-end program management of our PEO Benefits Renewal, working cross-functionally with our product and customer-facing teams to define workstreams, set milestones, manage cross-functional accountability, surface risks proactively, and ensure on-time delivery Lead the mid-year risk management motion – coordinate monthly risk identification, proactive quoting, client outreach, and engagement to proactively manage risk and optimize outcomes for our 12/1 benefits renewal Develop, document and scale PEO Benefits processes and cross-functional workflows in conjunction with our product and customer-facing teams Facilitate operational rhythms: program reviews, executive readouts, retrospectives, and milestone tracking. Work directly with all Rippling PEO brokers, benefits partners, and key PEO partners to best serve our shared members Partner with our Product, Engineering, and Legal teams to improve systems and resolve issues Use data to drive fact-based decision-making to optimize our PEO benefits offering and plan performance Autonomously execute special projects related to PEO benefits and managing our book of PEO customers Serve as a Rippling PEO benefits expert to support internal and external teams What you will need A minimum of 7+ years operational experience in a fast-paced Tech, Fintech, and/or Insur-tech company Demonstrated experience leading large, cross-functional programs with multiple concurrent workstreams; a strong project management track record with an ability to drive accountability across teams you don't directly manage Strong analytical skills; proven ability to manipulate and interpret data to produce insights and recommendations across large/diverse datasets; a data-forward approach to all decision-making A resourceful self-starter with excellent organizational and time management skills; comfortable managing many concurrent workstreams and context-switching fluidly under pressure Ability to execute with conviction and good judgment with limited guidance; thrives in ambiguity and adapts quickly Exceptional writ