Remote, sf
51 - 100 employees
11 - 25 engineers
$5m - $10m funding
Series a

Our mission is to provide access to health coverage under the Affordable Care Act. We believe that EVERYONE deserves high quality, affordable health coverage. We've enrolled over 9 Million people and process more than 1 in 3 applications.

HealthSherpa photo 1 HealthSherpa photo 2 HealthSherpa photo 3 HealthSherpa photo 4 HealthSherpa photo 5

Why join us?

  • Growth. HealthSherpa has 2x'd four years in a row, and is the dominant marketplace in our category. Our nearest competitor has <20% of our transaction volume / GMV. We are highly profitable - 2021 net profit exceeds the total amount of external funding we've taken (!)

  • Impact. HealthSherpa has enrolled over 9 million low income Americans in high quality ACA-compliant (Obamacare) health coverage. These 9 million people have received over $50b in government subsidies to pay for their health coverage, and the typical enrollee is paying <$10 a month for high quality, comprehensive health coverage that costs ~$825 a month. We have a large, direct impact on solving the problem of access to healthcare for the lowest-income, most vulnerable people in our society.

  • Commitment to Diversity, Equity and Inclusion. We believe that more representative teams do a better job of serving their customers. ACA enrollees disproportionately come from underrepresented and underserved communities, and we are committed to building a team that represents the people that we serve.

Engineering at HealthSherpa

Engineering team and processes

Team of 12 managed by a Director of Engineering who reports to the CTO. Engineers join workgroups/product teams that are dedicated teams of 4-6 people including Marketing, Design, Sales, Account Management. There's a lead engineer in each workgroup. These teams are responsible for creating their own Roadmaps and prioritizing their 2-week sprints. The goal is to give folks more ownership, encourage them to share ideas and learn from one another, and work towards the company goals as a team.

Technical Challenges

Scaling complex processes securely - HealthSherpa enrolls more than 1 in 3 enrollees, and that volume is highly seasonal. Building out new products - HealthSherpa is expanding into two new markets, so there are opportunities to build out a new product from the ground up.

Projects you might work on
  • Build out quoting and enrollment for a new market.

  • Build growth/monetization tests and productionize successful tests.

  • Scale infrastructure to handle open enrollment volumes.

Tech stack
Ruby on Rails
Elastic Search

Working at HealthSherpa

We put enrollees first. We always use data to inform our priorities and what we work on. We don't welcome egos or I players. We work together and support one another. We over-communicate and share constructive, respectful, and kind feedback. We are a diverse & inclusive team of people from different classes, education, countries, cultures, and identities. We are mindful, check our biases and always work to improve our communication & processes. Most importantly, we share a strong motivation to help people access health coverage under the ACA.

Diversity and Inclusion

HealthSherpa has signed the Founder's Commitment started by Kapor Capital. Signing this commitment means we are dedicated to building a company that bakes diversity & inclusion into our business. We firmly believe that diverse and inclusive teams are more innovative because they do a better job of incorporating valuable perspectives into their products’ DNA. They also do a better job of serving all of their customers by better understanding their wants and needs and communicating more effectively with them. Ultimately, diverse teams build better products and better serve their customers.

We strongly believe in diversity and inclusion of all people, of all genders, races, ethnicities, sexual orientations, shapes, sizes, educational backgrounds, religions, abilities, socioeconomic backgrounds, immigration statuses, and more.

Perks & benefits
  • Free Food

    Lunches, coffee / tea, and snacks are provided by HealthSherpa.

  • Flexible Hours

    We care most about getting things done at a high-bar of quality. We understand that life comes first and we are accommodating to work hours for our team members.

  • Health Insurance

    Health, Dental, and vision coverage for you, your spouse or domestic partner, and any/all dependents.

  • 401(k) Contribution

    Company matching 100% of first 3% and 50% of next 2% of your salary in contributions.

  • Maternal/Paternal Leave

    2 months of 100% paid parental leave to the eligible parent serving as the primary or secondary caregiver following the birth or adoption of a child.

  • Work from Home


  • Team Activities

    Dinners, Diversity & Inclusion events, Conferences, etc.

  • Pet Friendly
  • Transportation
  • Other

    Employee Assistance Program

  • Philanthropic Contributions
  • Prioritizes diversity in hiring
  • Serves underrepresented populations
  • Social impact driven
  • Women-led company
  • LGBTQ+ friendly
  • Minority-led company
Our Team by the Numbers

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