About the Role
We’re hiring for a full-time, in-office Sales position at our vibrant downtown Chicago office, located in Willis Tower. You’ll need to be able to commute to the office daily.
This opportunity comes with paid training, commuter perks, and unlimited bonus potential—plus plenty of other benefits.
We’re a fast-growing health and wellness company dedicated to improving the lives of Medicare recipients by helping them find the right insurance plans and services. Situated in the heart of the city, we value a lively, collaborative in-person culture.
Earnings & Growth
Monthly bonus potential: Average $1,000–$3,000
First-year total compensation: Typically $55,000–$70,000
Starting hourly rate: $20.00/hour
What You’ll Be Doing
As a Licensed Benefits Advisor, you’ll be the voice that helps individuals find Medicare coverage that fits their needs. No prior license is required—we’ll cover the training and licensing support to set you up for success.
This is a fast-paced, high-volume sales role where you’ll handle 50–100 calls per day—most of which are live inbound calls from individuals exploring their Medicare options.
Day-to-day responsibilities include:
Taking inbound sales calls to guide individuals through Medicare plan options and enrollments.
Making follow-up outreach calls to help clients review or update their coverage.
Educating customers on plan benefits so they can make confident decisions.
Staying compliant with all CMS and state regulations.
Collaborating with teammates and sharing feedback to improve processes.
What We’re Looking For
Comfortable in a goal-driven, performance-based environment with high daily call volume
Excellent communication and people skills
Enthusiastic, motivated, and a team player
Tech-savvy and able to multitask across multiple systems while on calls
Sales experience is helpful but not required
Must be able to complete licensing requirements and a background check
Bachelor’s degree preferred but not required
Benefits & Perks
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 growth and development opportunities
Employee referral incentives
Fun, energetic team culture with outings and events
Schedule
This is a full-time, 40-hour/week role (Monday–Friday). Flexibility is important, especially during peak Medicare season (Oct–Dec). Shift options include:
8:00 AM – 5:00 PM
8:30 AM – 5:30 PM
9:00 AM – 6:00 PM
9:30 AM – 6:30 PM
10:00 AM – 7:00 PM
Requirements
Valid driver’s license