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PEO Benefits Advisor

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Rippling
Full Time position
Listed on 2026-07-24
Job specializations:
  • Sales
    Insurance Sales
Salary/Wage Range or Industry Benchmark: 85000 - 110000 USD Yearly USD 85000.00 110000.00 YEAR
Job Description & How to Apply Below

About this position

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.

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 and rates, and present to prospective and existing Rippling customers. This role is cross‑functional, directly impacting financial performance, and involves designing scalable processes to expand the team, minimize operational burden through software automation, and maintaining high service quality for customers.

What

you will do
  • Interface with prospects and customers to collect data required 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 and rates, and enter plan selections.
  • Partner with Rippling Sales Executives and PEO Account Executives to guide clients through their insurance options.
  • Establish processes that professionalize our workflow while optimizing efficiency and accuracy.
What you will need
  • Two 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, both verbal and written.
  • Strong project management and organizational skills, with high attention to detail and excellent work product.
  • Solid Google Workspace skills, particularly Google Sheets.
  • An active Life, Accident & Health license.
Pay range for this role
  • US Tier 1: 100,000 – 110,000 USD per year
  • US Tier 2: 90,000 – 100,000 USD per year
  • US Tier 3: 85,000 – 95,000 USD per year

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

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