PEO Benefits Advisor
- Location
- Chicago, IL
- Listed
- Today
About the role
The PEO Benefits Advisor will partner with Rippling Account Executives, Account Managers and PEO Account Executives to help quote, provide comparative analysis of our health insurance plans/rates, and present to prospective and existing Rippling customers. This is an exciting opportunity to be a crucial part of our fast-growing PEO.
While working directly with customers, Account Executives and Managers, PEO Account Executives and the Rippling product, you'll also help design scalable processes to expand the team as we grow, while working cross-functionally to minimize the operational burden through software automation. It's a highly cross-functional role with direct impact on our financial performance.
What you will do
- Interface with prospects/customers to assist in collecting the data needed to quote the group with our third party Underwriters.
- Provide timely and accurate comparative analysis of existing plans and plans available on the Rippling PEO.
- Leverage the Rippling product to evaluate insurance plans/rates, and enter plan selections.
- Partner with Rippling Sales Executives and PEO Account Executives to guide clients through their insurance options.
- Establish processes to both professionalize our process while optimizing efficiency and accuracy.
What you will need
- 2 or more years in a client-facing role in the health insurance industry
- Deep understanding of the health insurance market
- Excellent client-facing communication skills, in both verbal and written communication
- Strong project management and organizational skills: high attention to detail with excellent work product, time management, and execution
- Solid Google Workspace skills, particularly Google Sheets
- An active Life, Accident & Health license is preferred
Additional information
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 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 40 mile 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.
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-remote
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 $1.2B 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 official communication will only be sent from @ Rippling.com addresses.
Equal opportunity and legal notices
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.
From Rippling's careers page, first listed on Rolev.ai on November 12, 2026. Rolev.ai is not the employer.
How Rolev.ai helps with this application
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Common questions
Where is the PEO Benefits Advisor job at Rippling located?
This PEO Benefits Advisor position at Rippling is located in Chicago, IL. Always check Rippling's application page for specific state eligibility or relocation policies.
How do I apply for the PEO Benefits Advisor position at Rippling?
This listing links directly to Rippling's Rippling application page. You can apply directly on Rippling's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Rippling application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.