Entry Level Inside Sales

About Us

This is an in office position.

You must be able to commute to our office in downtown Chicago at the WILLIS TOWER!

Paid Training, Commuter benefits, Uncapped bonus potential more!

OneDigital Advanced Health, based in the heart of downtown Chicago, improves lives by providing outstanding health and wellness products and experiences for Medicare recipients.

Monthly Bonus Potential & Pay

Base Pay - $20.00 per hour to start, with room for growth based on performance incentives. The average monthly bonus ranges from $1,000-$3,000 per month based on your performance. Typical 1st year earnings are between $55,000-75,000 per year.

We are so excited to have our employees fully in office! This is not a remote position.

About the Role

Are you interested in being part of a high-growth startup organization that values you and provides direct support to achieve your sales goals and a high earning potential?

As a Licensed Benefits Advisor, you will help individuals through the important decision-making process of selecting a Medicare health insurance plan that matches their needs and assist the consumer in enrolling in the best plan. You will receive live, inbound calls from consumers that may be eligible for better Medicare options. You will be responsible for providing an outstanding customer experience while achieving monthly sales goals. We are a growing and competitive team within a fun and supportive work environment. This fast-growth provides a variety of attractive career paths and performance based incentives are available to all of our licensed agents.

Not a licensed agent? Not a problem! All training courses and required insurance licensing will be provided and paid for. We provide hands-on training, webinars, and study groups to set you up for success and pass your insurance licensing exam.

Responsibilities

• Field live, inbound calls and effectively sell health insurance plans and products to our customers.
• Outbound to potential customers to revisit their Medicare options.
• Guide consumers through the plan selection and application process.
• Quickly learn insurance product offerings and serve as a subject matter expert for health insurance plans.
• Provide an excellent customer experience for consumers.
• Comply with Federal CMS and State legal requirements and standards.
• Provide continuous feedback throughout the sales floor by raising opportunities for improvement to management.

Qualifications

• Ability to work in a fast paced, competitive, and performance-driven environment.
• Professional and motivated self-starter.
• Previous sales experience is a plus, but not required.
• Excellent communication and interpersonal skills.
• Computer proficiency with the ability to use multiple screens.
• Must be able to successfully complete all licensing and legal background requirements.
• Bachelor's degree preferred, but not required.

Benefits and Perks

• Paid Time Off
• High earning potential for bonuses
• Commuter Benefits
• Company Health Plan
• Dental and Vision
• Long Term and Short Term Disability
• Basic and Voluntary Life Insurance
• 401K Matching
• Professional growth opportunities
• Employee referral bonuses
• Competitive team within a fun and supportive work environment
• Team outings, company sponsored events and sporting activities

Work Schedule

This is a full-time position with 8-hour shifts, Monday through Friday, from January through October.

Shift assignments are performance-based and may vary over time.

Shift Availability

All candidates must be open to working any of the following shifts:

8:00 AM – 5:00 PM

8:30 AM – 5:30 PM (Mandatory during initial 4–5 week training period)

9:00 AM – 6:00 PM

9:30 AM – 6:30 PM (October–December only)

10:00 AM – 7:00 PM (October–December only)

AEP Expectations

Annual Enrollment Period (AEP) is our peak season, running from October 15 – December 7. During this time, we have heightened operational demands, and all team members are expected to be fully available.

AEP 2025 Schedule

• Mandatory Availability: All trainees and sales agents must be available throughout AEP (Oct 15 – Dec 7).
• Extended Hours: From November 1 – December 7, a Monday–Saturday schedule is required. Generous overtime opportunities are available.
• PTO Blackout Period: No time-off requests will be approved between October 15 and December 7.
• Holiday Office Closure: Offices will be closed (unpaid) from December 15 – January 1. However, performance-based incentives may qualify you for holiday pay.