PEO Benefits Operations Manager

Responsibilities

• Lead end-to-end program management of PEO Benefits Renewal, working cross-functionally with product and customer-facing teams to define workstreams, set milestones, manage accountability, surface risks, and ensure on-time delivery.
• Lead mid-year risk management motion, including monthly risk identification, proactive quoting, client outreach, and engagement to manage risk and optimize outcomes for benefits renewal.
• Develop, document, and scale PEO Benefits processes and cross-functional workflows with product and customer-facing teams.
• Facilitate operational rhythms such as program reviews, executive readouts, retrospectives, and milestone tracking.
• Work directly with Rippling PEO brokers, benefits partners, and key partners to serve shared members.
• Partner with Product, Engineering, and Legal teams to improve systems and resolve issues.
• Use data to drive fact-based decision-making to optimize PEO benefits offering and plan performance.
• Autonomously execute special projects related to PEO benefits and managing book of PEO customers.
• Serve as a Rippling PEO benefits expert to support internal and external teams.

Requirements

• Minimum 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; strong project management track record with ability to drive accountability across teams without direct management.
• Strong analytical skills; proven ability to manipulate and interpret data to produce insights and recommendations across large/diverse datasets; data-forward approach to decision-making.
• Resourceful self-starter with excellent organizational and time management skills; comfortable managing concurrent workstreams and context-switching under pressure.
• Ability to execute with conviction and good judgment with limited guidance; thrives in ambiguity and adapts quickly.
• Exceptional written and verbal communication skills; ability to distill complex topics into concise points and communicate program status, risks, and trade-offs clearly to senior leadership.
• Collaborative, cross-functional mindset with proven ability to influence and motivate teams across organizational boundaries without direct authority.
• Strong alignment with leadership principles: Go and See, and Are Right, a Lot.

Nice-to-Haves

• Experience in benefits, PEO, or insurance operations.
• Background working with brokers, carriers, and benefits partners.