Fair Square Medicare

The health insurance agent you wish your parents had.

GM @ Fair Square Medicare

San Diego, CA / Remote
Job Type
6+ years
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Daniel Petkevich
Daniel Petkevich

About the role

What you’ll do

You’ll lead Operations for www.fairsquaremedicare.com 's core business, which recently passed $3M ARR and is growing 30% MoM. We take a senior from knowing nothing about Medicare to feeling confident they have the best health insurance their budget allows. You’ll:

  • Own monthly revenue growth goals and the brokerage P&L
  • Manage a sales team of 20+ agents
  • Develop and track KPI's
  • Implement processes and incentives to drive the above.

Who you are

You have a track record of successful P&L ownership, developing creative operations strategies, and delivering outcomes. You are known as an all-star generalist with an ownership mentality.

Who you'll work with


Dan founded Fair Square Medicare after watching his parents struggle through the Medicare shopping process. He previously was the technical co-founder at Trim (post Series A; valued @ > $30M), Octane Lending (Growth stage, valued @ > $300M) and has held product and growth roles at Redfin, the Climate Corp, and AppDynamics. He studied Physics at Yale.


Chris is the health insurance agent Dan's parent's found after a long and painful search. They love him. He's helped thousands of seniors across the U.S. navigate the minefield of Medicare. His core value: "treat clients as if they're your family".


Tej is Fair Square Medicare's head of growth. He joined after completing a stint in Bain's Private Equity Group, running a "nothing to sneeze at" house flipping business, and studying CS at Washington University in St. Louis.


Ben is Fair Square Medicare's Head of Partnerships. He previously founded The Civic Group (a Real Estate Private Equity company with $13M AUM), and ExpertArmada (a legal-tech company with $40,000 ARR). Prior to that, he worked in product and management roles at Bridgewater Associates. He is a licensed attorney in CA, and studied Government at Dartmouth.

Our Culture

Treat our users like family

We are building for our own parents.

Be kind

We believe that your character as a person is shown by how you treat others. Especially when everything isn't hunky dory.

"The megalomaniac pleasure of creation produces a type of elation which cannot be compared with that experienced by other mortals."

You deeply love being on the ground floor and building a company.

Think clearly so that we can disagree productively.

Your mind is a function that returns a point of view given a set of data and assumptions. Understand this function's body and explain it to the team so that they can review it and help you make sure it works.

Tech is a means to a great customer experience

We love to geek out about how Graphql >>> REST. And we use it because a strongly opinionated API layer helps us iterate faster toward a product our users love.

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