Fair Square

Bringing delight, health, and financial security to people over 65

Head of Product

United States / New York, NY, US
Job Type
6+ years
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Daniel Petkevich
Daniel Petkevich

About the role

The Role

You will own technology driven outcomes at Fair Square Medicare. Including:

  • Monthly engagement

  • Annual client retention

  • Growth

  • New product development - you'll talk to users daily and run experiments to find ways our products can make their light more delightful and healthier.

To accomplish these ends, you will work with a team of six engineers. You will be a servant leader to them, continuously crunching user data to show a path for what to build next and creating delightful and pixel perfect mocks.

Your Background

You are someone who is:

  • Quantitatively fluent and especially so in the tools use to analyze product usage, like Posthog or Amplitude. You can write SQL in your sleep.

  • You can create whip up pixel perfect mocks in Figma. You have a workflow for taking components from figma, to the design system in code to production.

  • You have deep empathy for our users. You understand there's an art to UX.

  • You have deep empathy for engineers. Engineers respect you. You probably were an engineer in the past.

  • You've built beautiful digital products before that have delivered value. Maybe you're a former founder or owned product at an earlier stage company. You probably didn't work at FB or Google after 2010.

  • Experienced. You have reps with all of the above bullets.

About Fair Square

The Company

In 1935 the Social Security Act set the retirement age to 65. At the time, the average life expectancy of an American was 62.

A lot has changed in the last 83 years. The average American now lives until 79. The people turning 65 today were 45 during the first dot-com boom. The fastest growing segment on Tik-Tok is seniors. It took 20 years, but the internet has finally arrived for seniors.

But most of the products that seniors use are distinctly “pre-web” - they’re cumbersome and exploitative.

When seniors buy healthcare, they have to talk to an insurance agent over the phone. These agents are exactly what you’d expect - they don’t know much about health insurance and they push Mom and Dad into the plan they get the highest commission on.

When seniors look to for liquidity, reverse mortgage brokers take advantage of their financial illiteracy.

When seniors look for companionship, they find themselves isolated in the suburbs they originally moved to to raise a family.

We are acutely aware of these problems because we see our own parents experience them.

Fair Square is fixing them.

Fair Square’s goal is to be a company seniors trust. To advise them on health insurance and financial planning. To find them a book club or an Art History lecture at a local community college. To have the customer experience of a five-star hotel and the care and respect of a relative. We started by building a customer obsessed health insurance brokerage for seniors. We’ve worked with 10,000 people across the United States. Our NPS score is 98, compared to an industry average of 13.

Join us and build the rest.

Our Values

  • Winning is really hard, takes a lot of work, and is not easy
  • We are an NBA All-Star team, not a family. This is a place for people who want to do the best work of their life and build a generational company
  • Ego is the greatest impediment for personal growth. There is immense utility in humility.
  • Be kind to your teammates
  • Treat our clients like family
  • Do the best work of your life
  • Always raise the standard
Fair Square
Team Size:20
Location:New York
Daniel Petkevich
Daniel Petkevich