×
Register Here to Apply for Jobs or Post Jobs. X

Inside Sales Representative

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: SkyBox Capital
Full Time position
Listed on 2026-03-13
Job specializations:
  • Sales
    Insurance Sales, Inside Sales
Salary/Wage Range or Industry Benchmark: 55000 - 75000 USD Yearly USD 55000.00 75000.00 YEAR
Job Description & How to Apply Below

Are you ready to take your career to the next level with a sales position that offers uncapped earning potential and significant growth opportunities
?

Join a fast-growing organization that values your contributions and provides the training and resources you need to succeed. In this high-energy sales role, you’ll have the opportunity to earn strong performance bonuses while being supported by a team dedicated to your success.

If you’re motivated, competitive, and eager to build a long-term career with a company that promotes from within
, we want to hear from you.

Position Overview

This is an in-office position located in downtown Chicago and requires the ability to commute to the office daily.

What We Offer
  • Paid training and licensing
  • Commuter benefits
  • Uncapped bonus potential
  • Career advancement opportunities
Compensation Monthly Bonus Potential

Top performers earn $1,000–$3,000+ per month in bonuses depending on performance.

Typical first-year earnings range from $55,000–$75,000 including bonuses.

About

The Role

As a Licensed Benefits Advisor
, you will help individuals navigate the process of selecting a Medicare health insurance plan that best fits their needs and assist them in completing enrollment.

You will handle live inbound calls from consumers interested in reviewing their Medicare options and guide them through plan selection while delivering an exceptional customer experience.

You’ll be joining a high-growth sales team in a competitive but supportive environment
, where strong performance leads to advancement opportunities.

Not currently licensed? No problem.

We provide paid training, study support, and licensing preparation to help you pass your insurance exam and start your career in the industry.

Responsibilities
  • Handle live inbound calls and present appropriate health insurance plans to prospective customers
  • Conduct follow-up outbound calls to individuals reviewing Medicare options
  • Guide consumers through plan comparison and enrollment
  • Quickly learn insurance products and become a subject matter expert
  • Deliver a high-quality customer experience on every interaction
  • Maintain compliance with CMS and state regulatory requirements
  • Provide feedback to leadership on opportunities to improve the sales process
Qualifications
  • Ability to thrive in a fast-paced, performance-driven sales environment
  • Strong communication and interpersonal skills
  • Self-motivated and results-oriented
  • Previous sales experience is a plus but not required
  • Comfortable working with multiple computer screens and systems
  • Ability to pass insurance licensing and background requirements
  • Bachelor’s degree preferred but not required
Benefits & Perks
  • Paid Time Off
  • High performance bonus potential
  • Commuter benefits
  • Health, dental, and vision insurance
  • Short- and long-term disability coverage
  • Life insurance options
  • 401(k) with company match
  • Career growth opportunities
  • Employee referral bonuses
  • Team outings and company-sponsored events
  • Supportive, competitive sales culture
Schedule

Monday – Friday (8‑hour shifts)

Schedules are assigned based on performance. Candidates must be open to working one of the following shifts:

  • 8:00 AM – 5:00 PM
  • 8:30 AM – 5:30 PM (mandatory training schedule)
  • 9:00 AM – 6:00 PM
  • 9:30 AM – 6:30 PM
#J-18808-Ljbffr
To View & Apply for jobs on this site that accept applications from your location or country, tap the button below to make a Search.
(If this job is in fact in your jurisdiction, then you may be using a Proxy or VPN to access this site, and to progress further, you should change your connectivity to another mobile device or PC).
 
 
 
Search for further Jobs Here:
(Try combinations for better Results! Or enter less keywords for broader Results)
Location
Increase/decrease your Search Radius (miles)

Job Posting Language
Employment Category
Education (minimum level)
Filters
Education Level
Experience Level (years)
Posted in last:
Salary