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Inside Sales Representative

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Skybox Capital

Chicago, IL (In Person)

$34,155 Salary, Full-Time

Posted 8 weeks ago (Updated 7 weeks ago) • Actively hiring

Expires 5/27/2026

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Job Description

Inside Sales Representative Chicago, IL Job Details Full-time 3 hours ago Benefits Paid training Commuter assistance Disability insurance Health insurance Dental insurance Paid time off Vision insurance 401(k) matching Opportunities for advancement Life insurance Referral program Qualifications Medicare Customer service Regulatory compliance CMS regulatory compliance Bachelor's degree Centers for Medicare and Medicaid Services (CMS) Health insurance sales Computer skills Outbound calling Communication skills Conducting sales calls Entry level Full Job Description 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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