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 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 Information
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. To request a reasonable accommodation, please email accommodations@rippling.com
Rippling highly values having employees working in-office to foster a collaborative work environment and company culture. For office-based employees (employees who live within a defined radius of a Rippling office), Rippling considers working in the office, at least three days a week under current policy, to be an essential function of the employee's role.
This 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
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.