PEO Benefits Operations Specialist

4 Months ago • 5 Years + • Operations • $90,000 PA - $104,500 PA

Job Summary

Job Description

Rippling is seeking a PEO Benefits Operations Specialist to join their foundational Benefit Ops team. This role involves assisting with the execution of operations and analytics for Rippling PEO benefits programs, including liaising with benefits partners, developing scalable processes, supporting annual benefits renewal, and executing data analysis. The specialist will work with external partners and internal teams to scale the benefits program and will have a significant impact on Rippling's financial performance. Key responsibilities include leading billing and enrollment reconciliations for medical, dental, and vision carriers, handling escalated benefit cases, developing and scaling PEO Benefits processes, supporting annual renewals, and using data to optimize the benefits offering.
Must have:
  • 5+ years operational experience in fast-paced Tech/Fintech/Insur-tech
  • Experience developing and supporting scalable processes
  • Strong analytical skills and data interpretation
  • Resourceful self-starter with excellent organization and time management
  • Ability to execute with conviction and good judgment with limited guidance
  • Excellent written and verbal communication skills
  • Collaborative and cross-functional mindset

Job Details

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.

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. This is an exciting opportunity to be a foundational member of the Rippling PEO Benefit Ops team. As a PEO Benefits Operations Specialist on the Rippling PEO team, you will assist with the execution of operations and analytics of the Rippling PEO benefits programs. This includes liaising with benefits partners, developing and implementing scalable processes, supporting the annual benefits renewal process, and executing data analysis for our modern, product-centric PEO. You’ll work directly with external partners and internal teams to scale a viable benefits program for the Rippling PEO. It’s a highly cross-functional role with a meaningful impact on Rippling’s financial performance.

What you will do

  • Lead billing and enrollment reconciliations across our medical, dental and vision carriers; perform periodic reporting, audits, and adjustments in collaboration with cross-functional teams, as needed
  • Support the handling of escalated or complex cases involving the administration of benefits; resolve complex benefit inquiries/issues generated by internal cross-functional teams
  • Develop, document and scale PEO Benefits processes and cross-functional workflows in conjunction with our product and customer-facing teams
  • Support the annual renewal process, working cross-functionally with Product, Engineering and client-facing teams
  • 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 5+ years operational experience in a fast-paced Tech, Fintech, and/or Insur-tech company
  • Demonstrated experience developing and supporting scalable processes
  • Strong analytical skills; proven ability to manipulate and interpret data to produce insights and recommendations across large/diverse datasets
  • A resourceful self-starter with excellent organizational and time management skills
  • Ability to execute with conviction and good judgment with limited guidance; require minimal direction in an ambiguous context to take action and then adapt quickly
  • Excellent written and verbal communication skills; ability to easily distill complex topics into concise points  
  • A collaborative and cross-functional mindset with a great sense of humor
  • Strong alignment with our leadership principles: in particular Go and See, and Are Right, a Lot.

Even if you don’t meet all of the requirements listed here, we still encourage you to apply. Skills can be used in lots of different ways and your life and professional experience may be relevant beyond what a list of requirements will capture.


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 accomodations@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.

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