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

TL;DR - Our core business is about to double off of a base of $XM revenue, and I need a GM for it. Likely former founder.

The Company

Our parents are subject to a health insurance shopping experience straight out of a Kafka novel. And we're fixing it.

Fair Square Medicare is building software to help seniors (our parents) make better healthcare decisions. Our first product is a customer obsessed (read: commission agnostic) health insurance brokerage for seniors. Incumbent brokers recommend plans that pay them the most commission, resulting in an industry-average NPS of 13 and 40% YoY churn. We recommend plans without regard for commission. Our NPS 95 and we keep 94% of our clients YoY. We’ve raised $19M from top VC’s including Define Ventures, Slow Ventures, and YC.

The Role

You will be the P&L owner for our brokerage.

The Outcomes You’ll Own

  • Brokerage Revenue - You’ll set revenue goals and deliver them. You’ll manage our brokerage operation and own the rate at which the brokerage converts calls from customers into revenue. You’ll work with our Head of Growth to understand and forecast demand.
  • Customer Experience - You’ll make sure our customers get the best Medicare shopping experience in the country. Quantitatively, you’ll own:
    • NPS - Keeping it at a sky-high 95.
    • YoY Retention - Keeping it above 90%
    • Results of quarterly customer satisfaction surveys
  • Compliance - We work with our existing compliance vendors to ensure all our brokers are properly licensed and appointed. You’ll manage them to ensure we are always 100% compliant.

Your Resources to Produce Outcomes

  • Our 15-person team of Medicare brokers. These are some of the most effective and empathetic brokers in the country.
  • Our eng team. You’ll work with eng to build internal tools for agents that drive the brokerage’s conversion rate.
  • Our analytics team. You’ll work with analytics to deeply understand the drivers of brokerage performance.
  • Our operations team. You’ll design processes for our ops team that drive the brokerage’s conversion rate.
  • Recruiters. You’ll systematize hiring/onboarding so that we can seamlessly scale our brokerage to meet future demand.
  • Bizops. We have a team of brilliant generalists from Bain, Goldman, and Deloitte to help with any of the above.

Your Skills

  • People Management - You need to manage and motivate a team of Medicare brokers, continuously recruit great people to it, and continuously remove those who aren’t performing and aren’t growing.
  • Quantitative Fluency - You want to reduce the brokerage to a few dashboards in a BI tool. Everyday, these dashboards will tell you if we’re on track for the month’s revenue goals and if we’re not, you can ask the questions - or maybe even write the SQL  - to figure out why.
  • Creating Systems Using SaaS - You can automate manual processes using the right SaaS tool.
  • You can work with engineers - Your bug reports are detailed instead of “it doesn’t work.”
  • Maturity - When you set a revenue goal, you hit it. If you’re going to miss, you let everyone know well in advance and know what we need to do differently for next month.
  • You’re fun. You’re nice. And you’re stoked to be here.

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