About the Position
This is a full-time, in-office role based in downtown Chicago.
You must be able to commute daily to our office at Willis Tower.
We offer paid training, commuter benefits, and uncapped bonus potential, along with a range of other perks.
We're a growing health and wellness company focused on improving the lives of Medicare recipients by connecting them with high-quality insurance plans and services. Located in the heart of the city, we’re proud to foster a vibrant, in-person work culture.
Earning Potential
Our monthly bonuses average between $1,000–$3,000, depending on your performance. First-year total compensation typically ranges from $55,000 to $70,000.
What You’ll Do
If you're looking to join a fast-paced, mission-driven company that values your contributions and provides tools to help you succeed, this might be the opportunity for you.
As a Licensed Benefits Advisor, you’ll assist individuals in choosing Medicare plans that best meet their needs. You’ll handle live, inbound calls from individuals who may be eligible for improved coverage and guide them through enrollment options while delivering an exceptional customer experience.
We provide robust training, coaching, and all necessary licensing support — no prior insurance license required to start.
Your Responsibilities Will Include:
Handling inbound sales calls and assisting individuals in selecting and enrolling in Medicare health plans.
Conducting follow-up outreach to help clients revisit or update their insurance choices.
Educating customers about different plan offerings and helping them make confident decisions.
Staying compliant with federal and state regulations (CMS).
Collaborating with your team and sharing feedback to improve processes and outcomes.
What We’re Looking For
Comfortable working in a performance-based environment.
Driven, enthusiastic, and team-oriented.
Strong communication and people skills.
Sales experience is helpful, but not required.
Proficient using computers and multitasking between systems.
Ability to complete all licensing requirements and background checks.
Bachelor’s degree preferred but not required.
Benefits
Paid time off
Monthly bonuses with high earning potential
Commuter benefits
Health, dental, and vision insurance
Short- and long-term disability
Life insurance (basic and voluntary)
401(k) with employer match
Career development and growth opportunities
Employee referral incentives
Positive and energetic team culture with regular outings and company events
Schedule
This is a full-time, 40-hour/week position with an 8-hour shift schedule, Monday–Friday. Flexibility is required, especially during peak seasons (Oct–Dec). Shift options include:
8:00 AM – 5:00 PM
8:30 AM – 5:30 PM (Initial training schedule – 6 to 8 weeks)
9:00 AM – 6:00 PM
9:30 AM – 6:30 PM (October–December only)
10:00 AM – 7:00 PM (October–December only)
Compensation
Starting at $20.00 per hour
Full-time in-person role at Willis Tower, Chicago, IL 60606
Requirements
Valid driver's license
Ability to reliably commute or relocate before starting