Fair Square Medicare

The health insurance agent you wish your parents had.

Content Marketing Lead

San Diego, CA / Remote
Job Type
Any (new grads ok)
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Daniel Petkevich
Daniel Petkevich

About the role

What you’ll do

You’ll lead content creation for www.fairsquaremedicare.com, the fastest growing and highest NPS health navigator for seniors. Our industry incumbents peddle misinformation and confusing content as a predatory sales practice. We are on a mission to fix that. In this role, you'll be responsible for:

  • Writing, editing, and designing engaging editorial, email, social media, and video content
  • Optimizing content on our website for organic search
  • Analyzing the performance of published content to identify high leverage opportunities
  • Collaborating with Growth, Partnerships, Engineering, Sales, Product, Ops, and more, to produce the most original and engaging content possible

Who you are

You're passionate about healthcare/health systems and improving the lives of senior citizens. You're excited about joining a fast-growing, mission-driven technology company. You have:

  • World class written and verbal communication skills. You know how to communicate both empathetically and professionally
  • A deep passion for producing high quality, zero defect pieces of content.
  • A reputation for making deadlines and effectively managing your time.
  • A growth mentality. You're looking for an opportunity to grow your skills in both content creation and content marketing strategy


Competitive compensation/equity, remote working opportunities, and access to Medical, HSA and 401k plans. Unlimited paid time off.

Suggested Qualifications

  • At least one year of marketing or editorial copywriting experience
  • A basic understanding of social media content creation
  • A basic understanding of video editing software, or a willingness to learn
  • A basic understanding of SEO best practices
  • Bachelor’s degree in Communication, Marketing, Business Management, or related field

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