Fair Square Medicare

The health insurance agent you wish your parents had.

Head of People

Anywhere / Remote
Job Type
3+ years
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Daniel Petkevich
Daniel Petkevich

About the role

Fair Square Medicare is one of the fastest growing technology companies in the country. We are a tech-enabled Medicare brokerage, just raised our Series A, and hiring a full-time Head of People. 

About Us

Fair Square Medicare is the health insurance shopping experience you wish your parents had. We:

  • Always recommend the right plan for our clients, even if it means we earn less commission 

  • Guide people through the entire Medicare process, from signing up for Parts A & B to enrolling in additional coverage.

  • Re-shop coverage for our customers every year to make sure they always have the plan that fits them best.

About the Role

We just raised our Series A, and are growing headcount rapidly. We are hiring full-stack engineers, business operations, and of course, the top 1% of licensed Medicare agents around the country.

This person will be responsible for managing the entire recruiting pipeline end to end, building a meaningful remote-first culture, and thinking strategically about our talent needs through time.

About You

You will succeed in this role if you have:

  • A friendly and personable demeanor

  • Proven track record building talent pipelines and hiring across a variety of roles

  • Ability to use or learn multiple technology platforms

  • Critical thinking and strategic thinking

Compensation & Benefits

  • Best-In-Class Pay

  • PPO Health Insurance

  • Flexibility to work remotely

  • 401K

Why you should join Fair Square Medicare

Your parents are subject to a health insurance shopping experience straight out of a Kafka novel.

And we're fixing it. We routinely save people from spending thousands in unnecessary premium, choosing plans that don't cover their doctors and prescriptions, and from going without insurance for a year. We're growing quickly in a $20B market, we've raised over $2M, and our revenue recurs for 15 years.

Fair Square Medicare
Team Size:20
Location:San Francisco
Daniel Petkevich
Daniel Petkevich