Redefine Healthcare With Us.

Define Ventures Partners

Senior Medicare Advocate

Fair Square Medicare

Fair Square Medicare

United States
Posted on Thursday, August 17, 2023
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. 94% 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 Medicare

Medicare is a government health insurance program - passed into law in 1965 - that almost every senior enrolls in when they turn 65. Back then, it was all the coverage a senior needed, but 55 years later, healthcare costs are sky-high, and folks need to purchase secondary insurance from a private carrier or face the risk of bankruptcy.

And here's the problem: the average senior has 50 options of secondary Medicare coverage, each of which can lead to drastically different health outcomes. Concretely speaking, if you choose the wrong plan, you could die a lot sooner than if you chose the optimal one.

About You

We’re looking for empathetic, driven, and mission-oriented people who are excited to join our team and guide American seniors through selecting the right health plan when they become eligible for Medicare.

Though we welcome experienced hires, no Medicare experience is necessary. Our training process (details below) will guide you through everything.

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.
  • Want to work in a fast-paced environment. We’re on our way to building a $100B company. We want people who are excited by this mission.
  • 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. A day in the life at Fair Square Medicare looks like this:
  • You answer calls from people who our marketing team has reached out to. There is no cold-calling. If it’s the first time you’re talking to them, you explain how Medicare works, how to decide between a Medicare Supplement and a Medicare Advantage plan and narrow in on a plan.
  • If it’s your second call with a client, you enroll them in a plan.
  • You follow up with clients you had a first call with.

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 interview Invitation via Hireflix

Prompt: Select a seemingly complex topic or concept that you know well. Explain or demonstrate it, in a simplified manner, for someone who is learning about it for the first time. (Time Limit: 3 minutes)
  • Round 3: Interviews with Hiring Manager & Team
  • Round 4: You’ll do a final interview with the company’s senior leaders. 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 all 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.


We compensate our agents with the following:

  • $35,000 base
  • $70 apiece for each of the first 30 closes in a month
  • $80 apiece for each of the next ten closes in a month
  • $130 apiece for any subsequent closes

Benefits & Perks
  • Aetna PPO. Full coverage of Silver-level premium
  • Dental & Vision Insurance
  • Fair Square University Training Program (paid)
  • Full Workstation (We provide your laptop, monitor, and peripheral devices)

  • You’ll receive incentive stock options in a growing tech company, backed by the same investors as DoorDash, Coinbase, Airbnb, and more

Our top agents enroll 50-60 clients a month and earn close to six figures. Agents who consistently perform and want to lead a team can earn six figures.