About the roleRippling 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 people leader and 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, coach, and develop a team of Benefits Operations Specialists, fostering a high-performance culture focused on operational excellence, customer outcomes, and continuous improvement.
- 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
- 2+ years of people leadership experience, including direct management of high-performing individual contributors with a track record of coaching, developing talent, and driving accountability.
- 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 written and verbal communication skills; ability to easily distill complex topics into concise points and a specific ability to communicate program status, risks, and complex trade-offs clearly and concisely to senior leadership
- A collaborative,cross-functional mindset and a proven ability to influence and motivate teams across organizational boundaries without direct authority
- Strong alignment with our leadership principles: in particular Go and See, and Are Right, a Lot.
Additional InformationThis role will receive a competitive salary + benefits + equity. The salary for US-based employees will be aligned with one of the ranges below based on location; see which tier applies to your location here.
A variety of factors are considered when determining someone's compensation-including a candidate's professional background, experience, and location. Final offer amounts may vary from the amounts listed below.
#li-hybrid
The pay range for this role is:
120,000 - 200,000 USD per year (US Tier 1)
108,000 - 180,000 USD per year (US Tier 2)
102,000 - 170,000 USD per year (US Tier 3)
