Demo

Entry Level Inside Sales Role

OneDigital Advanced Health
Chicago, IL Remote Full Time
POSTED ON 3/25/2026
AVAILABLE BEFORE 9/21/2026

$20/hr base uncapped monthly bonus potential

Full-Time | In Office | Paid Licensing | Paid Training


OneDigital Advanced Health is growing rapidly, and we’re looking for driven, motivated individuals to join our inside sales team. As an Entry-Level Licensed Benefits Advisor, you’ll take live inbound calls from individuals exploring their Medicare options, guide them through a needs-based assessment, and help them enroll in the plan that best fits their needs.


No insurance license? We pay for your training, licensing, and exam prep.

This is an in-office role located in downtown Chicago at the Willis Tower.


Responsibilities:


  • Take live, inbound consumer calls and recommend Medicare plan options
  • Conduct outbound follow-ups to our book of business
  • Meet monthly sales goals with strong support and coaching
  • Guide consumers through enrollment with a focus on world-class service
  • Learn and master our insurance product offerings
  • Adhere to all CMS and state compliance standards
  • Share feedback with leadership to improve processes


Qualifications:


  • Motivated, goal-oriented, and ready to grow in a fast-paced environment
  • Strong communicator with solid interpersonal skills
  • Sales experience is a plus—but not required
  • Comfortable using computers and multiple screens
  • Ability to complete licensing and background requirements
  • Bachelor’s degree preferred but not required


Compensation and Benefits:


  • $20.00/hr base pay
  • Uncapped monthly bonuses
  • Overtime incentives available during Annual Enrollment Period (Oct 15–Dec 7)


Benefits:

  • Paid Time Off
  • Medical, Dental, Vision
  • Short- & Long-Term Disability
  • Life Insurance
  • 401(k) Company Match
  • Commuter Benefits
  • Professional development & internal growth paths
  • Fun, competitive, supportive team environment
  • Team outings & company-sponsored events


Schedule:


Full-Time | Monday–Friday | In Person

Shifts vary by performance and business needs.

Training shift: 8:30 AM – 5:30 PM (first 4–5 weeks)

Possible shifts after training:

  • 8:00 AM – 5:00 PM
  • 8:30 AM – 5:30 PM
  • 9:00 AM – 6:00 PM
  • 9:30 AM – 6:30 PM (Oct–Dec only)
  • 10:00 AM – 7:00 PM (Oct–Dec only)


You can also apply directly through my link!

https://onedigital.wd5.myworkdayjobs.com/OneDigital/job/Entry-Level-Inside-Sales-Representative_R8308

Salary : $20

If your compensation planning software is too rigid to deploy winning incentive strategies, it’s time to find an adaptable solution. Compensation Planning
Enhance your organization's compensation strategy with salary data sets that HR and team managers can use to pay your staff right. Surveys & Data Sets
Employees: Get a Salary Increase
View Core, Job Family, and Industry Job Skills and Competency Data for more than 15,000 Job Titles Skills Library

Not the job you're looking for? Here are some other Entry Level Inside Sales Role jobs in the Chicago, IL area that may be a better fit.

  • Circle Logistics - Chicago/Orlando Chicago, IL
  • Job Description Entry Level Inside Sales Rep - Chicago, IL Circle Logistics is a 3rd party logistics firm focused on delivering our three core promises to ... more
  • 25 Days Ago

  • American Marketing & Publishing, LLC Schaumburg, IL
  • Build a career with unlimited earning potential as you get paid to call, connect with, educate, and close sales to local business owners. Develop your sale... more
  • 7 Days Ago

AI Assistant is available now!

Feel free to start your new journey!