# PEO Benefits Operations Manager

**Company:** [Rippling](https://hotfix.jobs/companies/rippling)
**Location:** San Francisco, CA, New York, NY
**Role:** Product Operations
**Salary:** $80k – $160k/yr
**Experience:** 7+ years
**Skills:** Project Management, Cross-Functional Leadership, Data Analysis, Process Development, Risk Management, Benefits Administration, Stakeholder Management, Executive Communication
**Posted:** 2026-04-30

> Lead end-to-end program management for PEO annual benefits renewal and mid-year risk management at Rippling. Requires 7+ years operational experience in tech/fintech/insurtech, strong cross-functional project leadership, analytical skills, and ability to thrive in ambiguity.

## Job Description

## 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.

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