Fortuna Health
TurboTax for Medicaid
Chief of Staff/Head of Business Development
About the role
What you'll do
We’re at an inflection point: more pipeline than bandwidth, more opportunity than capacity.
We’re hiring a Chief of Staff — the right-hand person and force-multiplier to the CEO. You’ll manage priorities, oversee internal operations, and spearhead the projects that move the company forward. The role will evolve as the company does, but the constant is this: you make the CEO more effective and Fortuna faster.
As an early hire at Fortuna, you’ll play a critical role in shaping how our service is delivered - and how our company scales. You will work directly on solving the most foundational problems for our clients and partners. We work fully in-person 5 days a week out of our NYC office, and believe deeply in the value of a focused, supportive, and tight-knit team.
What you'll own
- Executive Representation & Priority Management - Attend and lead meetings on the CEO’s behalf; track metrics and manage priority initiatives; ensure nothing falls through the cracks.
- BD & Partnerships - Develop frameworks for assessing opportunities and own new partnerships across healthcare, technology, and government. Where relevant, coordinate proposals, pilots, and compliance submissions.
- Internal Operations - Prepare agendas, decks, and meeting materials; manage All Hands programming; own the board meeting process.
- Policy & Thought Leadership - Own internal and external communication from the CEO. Track healthcare policy and partner with regulatory firms on changes. Operate Quorum (Fortuna’s convening of current and former state Medicaid directors) and steward advocacy with CMS, Medicaid agencies, and policy organizations.
- Special Projects - Collaborate with the CEO and cofounders on high-judgment work that doesn’t fit neatly elsewhere: strategic pricing, legal matters, managing consultant/advisor network, market and competitive research, and whatever the company needs most right now.
What we're looking for
Product Mindset
Our philosophy is that everyone should be product-oriented. We’re fundamentally building a consumer product for the masses. As such, we’re looking for an operations lead who’s motivated by delivering a seamless, user-centered experience. You care more about outcomes than org charts.
Ownership
There's plenty of greenfield, exploratory work to be done. We need someone to be able to take an ambiguous problem and run with it. As we gain traction with specific workflows, we would want you to own that end-to-end.
High Velocity
We are looking for a rockstar operator, someone who is energetic, motivated, and who brings serious focus and passion to everything they do. We need someone who can handle a high-output environment with both speed and detail-orientation.
Respectful Disagreement
We believe it's crucial to be able to openly disagree with anyone on the team. We are looking for someone who doesn't shy away from conflict, but is respectful and empathetic in their approach and always open to different ideas.
Humility
It's important to be able to admit when you're wrong. We are looking for a low-ego teammate who is able to take failures in stride and grow from them.
Requirements
- 4+ years in consulting, banking, or a high-growth startup. MBAs and former founders welcome!
- Ruthless at prioritization and timeliness
- Can seamless move between a spreadsheet and a stakeholder call
- Confident representing an organization externally — you can hold a room
- Genuine interest in healthcare, technology, and government/public policy
- Ability to work 5 days per week in-person in NYC
What we offer
- Competitive salary and equity ownership in the company
- Platinum health insurance plans
- Free lunch every day
- All commuter expenses covered
- $100/month wellness benefit
- Unlimited PTO
- 401k plan with company match
About Fortuna Health
What we do
Fortuna Health is redefining the consumer experience for Medicaid. We’re helping millions navigate Medicaid end-to-end from eligibility and enrollment to renewing coverage. We're backed by a16z, BoxGroup, YC, and top healthcare angels.
Our product is TurboTax for Medicaid. Today, ~90M Medicaid consumers navigate glitchy websites and long paper forms. The experience is so poor that procedural reasons (e.g., form errors, missing a notice in the mail) account for a staggering 75% of dis-enrollments. We believe this can only be solved with a modern and simple UX that is fundamentally consumer-centric.
Creating Value
The problem at the consumer level produces huge downstream consequences: There's over $50B of administrative waste and lost revenue suffered by Medicaid health plans, providers, and states. By making products that consumers want to use, we unlock immense value for these players. Our vision is to become the consumer-facing digital infrastructure that powers the $800B+ Medicaid ecosystem.
Who we are
We each have multiple years of experience in healthtech — Nikita started her career at Oscar and built pharmacy solutions at Truepill (YC S17), Cydney helped scale Halo Dx from seed to series C on the ops side, and Ben was the first engineer at Juniper (YC W21) where he helped scale the engineering team to 12. We have all had direct experience with Medicaid throughout our careers and have seen firsthand the challenges that affect the population.
We started Fortuna because we care about impact — the abysmal state of the Medicaid consumer journey means that the most underserved people in America can't access the benefits that they need and are entitled to. We believe this is a once in a lifetime opportunity to dramatically improve the human condition for 90M people, and we need the help of high-throughput, growth-minded builders to make it happen.
