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Inside Sales Representative

SkyBox Capital, Chicago, IL, United States


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

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