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 help American seniors select the right health plan when they become eligible for Medicare. We’ve found those with a track record of exceeding sales quotas excel in this role.

You will be the first person at FSM welcoming prospective, inbound clients and serving as their “Medicare concierge.”

No Medicare experience is necessary, though we welcome experienced hires. Our training process (details below) will guide you through everything you need to succeed and grow at FSM.

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 worked in insurance sales for too long (if at all). 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’ll answer inbound calls from people responding to our marketing. There is no cold-calling.

• You’ll qualify the inbound callers, provide answers to commonly asked Medicare questions, and schedule time with those qualified leads and one of our licensed Medicare Advocates.

• You’ll also handle calls from existing clients, and help our Medicare Advocates reschedule appointments as necessary.

Career Advancement

For those who exceed performance expectations, this role can provide an expedited path to becoming one of our licensed Medicare Advocates.

Our Interview Process

The typical timeline for our interview process is 7 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:

• Well versed in the basics of Medicare, and our company’s approach to helping seniors navigate their options

• Equipped with the tools and skills required to answer prospective clients’ frequently asked Medicare questions.

• Partner with other SDR colleagues throughout your onboarding process and have touch-points with other FSM team members. You’ll be trained alongside peers like you.

Completing FSU typically takes new hires about one week.

Compensation

We compensate our agents with the following:

• Cash

  • $30,000 base + commission

  • Total compensation - average: $55,000 OTE; exceptional $70,000 OTE

• Benefits & Perks

  • Aetna PPO. Full coverage of Silver-level premium

  • Dental & Vision Insurance

  • 401(k)

  • Fair Square University Training Program (paid)

  • Full Workstation (We provide your laptop and headset)

Excelling in this position can lead to promotion to Senior Medicare Advocate at FSM. Our top advocates 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.