Inside Sales Representative
Quick Summary
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.
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…
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…
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 readWhat We Offer
~1 min readNice to Have
~1 min readTop 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 readAs 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 readMonday – 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
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
Please let skybox-capital know you found this job on Jobera.
3 other jobs at skybox-capital
View all →Explore open roles at skybox-capital.
Similar Sales Development Rep jobs
View all →Browse Similar Jobs
Stay ahead of the market
Get the latest job openings, salary trends, and hiring insights delivered to your inbox every week.
No spam. Unsubscribe at any time.