Job description
About Us
We’re Fair Square Medicare, one of the fastest growing technology startups in the country. 95% of our clients would recommend us to a friend. 90% of our clients stay with us year over year.
Backed by some of Silicon Valley’s leading VCs, Forbes recently announced our $15M Series A to build upon our success and achieve our mission of helping every American senior successfully navigate one of the most daunting and byzantine systems ever known to man: Medicare.
About You
We’re looking for empathetic, driven, and mission-oriented people who are excited to join our team and help our clients navigate the Annual Enrollment Period, during which Medicare beneficiaries can choose to shop and enroll in new health coverage.
We’re looking for applicants who are currently licensed to sell Life and Health in their resident state . Our training process (details below) will guide you through everything Medicare-related. Bonus points if you have previous experience with a) medicare sales, b) teaching or c) customer support.
Our most successful team members:
Deeply care about our clients. Many of them entered the Medicare business after watching an older loved one struggle with the healthcare system.
Typically haven’t been in insurance sales for too long. We’ve found that too much time working at incumbents in this industry can be bad for a person’s spirit.
Tech literate. You don’t need people to help you with software and computers. You figure it out.
About the Role
This is a full-time remote position. Your day to day will involve helping our amazing clients decide whether to keep their existing coverage, or switch to a plan that’s a better fit. Most of these conversations will be via scheduled appointments. You will not be doing any cold calling or hard selling.
Success in this role requires enthusiasm for helping seniors with their healthcare, a strong grasp of our internal tooling used to quote and enroll different health plans, and a patient demeanor. Some other details:
Start Date: August 4th, 2025 (flexible based what’s best for you)
Training period: from start date to October 14, 2025
Contract end: Dec 8, 2025
- Medicare’s Annual Enrollment Period (AEP) runs from October 15th to December 7th.
Minimum hours
During the training period from August 4th to October 14th, you’ll be expected to work up to 40 hours per week.
During the AEP period, from October 15th to December 7th, you’ll be expected to work 40 hours per week.
Our Interview Process
The typical timeline for our interview process is 14 days. Here’s how our interview process works:
Round 1: Complete this application; we’ll contact you to confirm your resume
Round 2: Video submission displaying clear and concise communication
Round 3: Interviews with Team Leads
Round 4: Final interview with the company’s CEO. The next day you’ll either get an offer or not.
Our Training Process
Every new hire is paid to go through Fair Square University (FSU), our proprietary online training and certification program. As part of FSU you will become:
Licensed to sell health insurance in 25-50 states (we will cover all costs).
An expert in Medicare, and our company’s approach to helping seniors navigate their options.
Contracted and certified to sell health plans from every major insurance carrier in the country.
Partnered with other Medicare Advocate buddies throughout your program and have touchpoints with the leadership team and other FSM team members. You aren’t going through this alone.
Completing FSU typically takes new hires three to four weeks. Expenses are fully covered. When finished, you will not only acquire a new license and skillset, but you will also join an elite group and community: the country’s top 1% of Medicare experts.
Compensation
During the training phase, from your start date to October 14th, you will be paid an hourly rate of $30 per hour.
During AEP, from October 15th to December 7th, you will be paid an hourly rate of $35 per hour.
