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About the Role

This role is central to two of PEO's highest-visibility operational programs: the annual benefits renewal and the mid-year risk management motion. You will own these programs end-to-end, defining workstreams, driving cross-functional accountability, surfacing risks, and ensuring on-time delivery across a complex stakeholder map. This is an opportunity for someone who thrives on building operational structure, managing high-stakes programs in ambiguous environments, and making a measurable impact on financial outcomes.

Responsibilities

Lead end-to-end program management of PEO Benefits Renewal, defining workstreams, setting milestones, managing cross-functional accountability, surfacing risks, and ensuring on-time delivery.
Lead, coach, and develop a team of Benefits Operations Specialists, fostering a high-performance culture.
Lead the mid-year risk management motion, coordinating risk identification, quoting, client outreach, and engagement.
Develop, document, and scale PEO Benefits processes and cross-functional workflows.
Facilitate operational rhythms, including program reviews, executive readouts, retrospectives, and milestone tracking.
Work directly with PEO brokers, benefits partners, and key PEO partners.
Partner with Product, Engineering, and Legal teams to improve systems and resolve issues.
Use data to drive decision-making and optimize PEO benefits offering and plan performance.
Execute special projects related to PEO benefits and managing the book of PEO customers.
Serve as a Rippling PEO benefits expert to support internal and external teams.

Requirements

A minimum of 7+ years operational experience in a fast-paced Tech, Fintech, and/or Insur-tech company.
2+ years of people leadership experience, including direct management of high-performing individual contributors.
Demonstrated experience leading large, cross-functional programs with multiple concurrent workstreams.
Strong project management track record with an ability to drive accountability across teams without direct management.
Strong analytical skills and a data-forward approach to decision-making.
Resourceful self-starter with excellent organizational and time management skills.
Ability to execute with conviction and good judgment with limited guidance.
Exceptional written and verbal communication skills, with the ability to distill complex topics and communicate program status clearly to senior leadership.
Collaborative, cross-functional mindset and 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.

Skills

Program Management
People Leadership
Coaching
Talent Development
Accountability
Risk Management
Process Development
Workflow Management
Data Analysis
Decision-Making
Organizational Skills
Time Management
Communication Skills
Influencing Skills
Cross-functional Collaboration

Location

US-based

Work Type

Hybrid
Office-based

Experience Level

7+ years operational experience
2+ years people leadership experience

Salary/Compensations

Competitive salary + benefits + equity

Benefits

Top-notch benefits offerings

About the Company

Rippling PEO co-employs tens of thousands of worksite employees.
Rippling highly values having employees working in-office to foster a collaborative work environment and company culture.

Equal Opportunity

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, ancestry, physical disability, mental disability, medical condition, genetic information, marital status, sex, gender, gender identity, gender expression, age, sexual orientation, veteran or military status, or any other legally protected characteristics.
Rippling is committed to providing reasonable accommodations for candidates with disabilities who need assistance during the hiring process.