Chief of Staff

American healthcare providers spend hundreds of billions a year creating and optimizing health insurance claims. Payers spend a similar amount adjudicating them.

AI was supposed to fix this, but really it's making things worse. Providers use AI to improve claims; payers deploy AI to deny them. Both sides spend more; neither gains. So we're collapsing the middle of this negative-sum system and building the infrastructure that makes healthcare billing deterministic.

We're converting payer policies and medical notes into computable contracts grounded in formal logic - exposed via API and MCP, evaluated at the point of care, optimized for token efficiency, latency, and accuracy. We're replacing the adversarial back-and-forth between providers and payers with transparent, auditable, pre-agreed rules.

When we succeed, we'll materially reduce the cost of care for the American patient.

About us

On September 18 we announced a $100 million commitment led by our new partners at Thoreau, alongside our existing investors Bertelsmann Healthcare Investments, Twine Ventures, and Seedcamp.

Ten months ago this company was two people and a question: will my insurance cover this procedure? Now we are hiring across New York and London to become the intelligence platform both sides of American healthcare build upon.

The role

Chief of Staff to the CEO. An operating role with direct ownership across revenue, operations, strategy, and product.

You’ll work directly with Sohum (CEO, MD) and sit at whatever is the company’s binding constraint that month: a payer pilot, a pricing decision, a hiring sprint, an investor deliverable.

The split we’re envisioning (it will flex as we scale):

Operations (~40%). The operating system of a company growing from a founding team into a trans-Atlantic organization: investor and board materials, hiring loops, finance.

Commercial (~40%). Oversee the back half of every deal: pricing and packaging, proposals and order forms, contract negotiation alongside our counsel, and the close plan from verbal yes to signature.

Strategy (~20%). Analysis that changes what we do next: pricing, which side of the market to lean into next, which buyer segment we enter.

Real work from our last 90 days that this seat would have owned: onboarding a vendor’s pilot end to end; a pre-send adversarial review of a client contract; a competitive teardown that changed our positioning; our regular investor updates and board meeting prep.

What success looks like at 12 months

The company’s operating rhythm (planning, reporting, hiring) exists because you built it.

You own a P&L-shaped piece of the business, and we’re discussing which leadership seat you take.

Where it goes

Treat it as a tour of duty: do this brilliantly for 18-24 months and the natural next seat is a Head of Operations role. Or you leave to start your own company with our full support.

About you

You're an ex-founder or have worked in high performance industries (IB, VC, consulting, startups)

You have 5+ years of professional experience, ideally with some experience of healthcare or life sciences

You have a consistent track record of delivery

You reason from first principles

You are an excellent communicator - at Penelope, we think in writing and favor memos over slides.

You are AI-native - when you face hard problems repeatedly, your first instinct is to ask how you can automate the solution.

You love unpredictability - no day is the same at Penelope

Not a fit if

You need defined lanes to feel grounded.

You want to advise on the work rather than do it.

You’re looking for a 9-to-5.

What we offer

$200k-300k + meaningful early equity

New York, in-office, with some flexibility

Company laptop and a generous software budget

Learning and development budget

We also offer a $10k referral bonus (after the referred hire finishes a 3 month probation period). Penelope Health is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, national origin, sex, sexual orientation, gender identity, age, disability, veteran status, or any other characteristic protected by law.