Fair Square Medicare

The health insurance agent you wish your parents had.

BizOps @ Fair Square Medicare

San Diego, CA
Job Type
1+ years
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Daniel Petkevich
Daniel Petkevich

About the role

What you’ll do

You’ll lead Business Operations for www.fairsquaremedicare.com, the fastest growing and highest NPS health navigator for seniors. In this role, you'll be responsible for:

  • Owning direct strategy pieces and the key metrics that feed them
  • Tackling a variety of problem solving challenges across core business functions, from problem identification to solution implementation
  • Acting as a culture carrier. We're a team of growth minded, first principles thinkers building healthcare solutions for our parents. We love working together and want you to feel the same!
  • Collaborating with Engineering, Growth, Partnerships, Product, Sales, Ops, and more

Who you are

You use data to solve problems and love executing at every level. Or, you are known as an all-star generalist with an ownership mentality.

  • Proficiency in data analytics (SQL, R, or Python), or an ability and willingness to learn these tools.
  • Excellent written and verbal communication.
  • Experience in growth/ops at fast-pace startups or at a top management consulting firm is a plus.

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