skybox-capital
New

Inside Sales Representative

ChicagoFull timemid
SalesSales Development Rep
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Quick Summary

Overview

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.

Key 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…

Requirements Summary

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…

Technical Tools
SalesSales Development Rep

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.

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

What We Offer

~1 min read
Paid training and licensing
Commuter benefits
Uncapped bonus potential
Career advancement opportunities

What We Offer

~1 min read

Nice to Have

~1 min read

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

~1 min read

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.

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

Responsibilities

~1 min read
  • 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

Requirements

~1 min read
  • 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

What We Offer

~1 min read
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

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

Location & Eligibility

Where is the job
Chicago
On-site at the office
Who can apply
Same as job location

Listing Details

First seen
May 6, 2026
Last seen
May 7, 2026

Posting Health

Days active
0
Repost count
0
Trust Level
42%
Scored at
May 6, 2026

Signal breakdown

freshnesssource trustcontent trustemployer trust
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skybox-capitalInside Sales Representative