Founding Head of Engineering
Please mention DailyRemote when applying
AI Summary
Architect and build the core intelligence layer for a federal arbitration platform, focusing on data normalization and LLM-powered reasoning. Lead the engineering organization by recruiting a high-caliber team and establishing security and compliance postures.
Founding Head of Engineering
Build the intelligence layer for a multi-billion-dollar federal arbitration market.
Location: San Francisco or Remote | Full Time
Why This Exists
A federal arbitration system now determines billions of dollars in healthcare payments each year. Providers win the vast majority of disputes — yet most eligible claims are never filed because the process is manual, fragmented, and resource-intensive.
The No Surprises Act created the framework. The market already exists. Today, it runs on spreadsheets, consultants, and static playbooks. We’re building the first intelligent system designed to operate inside this market.
Our platform will:
- Ingest and normalize messy claims data from disparate RCM systems
- Identify disputes with positive expected value
- Model win probability and award size across payers and geographies
- Generate structured arbitration submissions using LLMs
- Track outcomes and continuously refine strategy
- Orchestrate thousands of disputes with auditability and compliance
This is not workflow automation. It’s a continuously learning system operating in a repeated, adversarial market. Counterparties adapt. Regulations evolve. Strategy compounds.
The architectural decisions made in the first year will shape the company for the next decade. This role is central to that.
Why This Is Hard (and Interesting)
Claims data is inconsistent, incomplete, and domain-heavy. Arbitration decisions are partially opaque. Payers change behavior over time. Regulatory guidance evolves through litigation. Every decision feeds back into future strategy.
The system must operate across distributed data infrastructure, applied machine learning, LLM-powered reasoning, optimization under uncertainty, and healthcare-grade regulatory constraints — all at once.
If you enjoy clean CRUD SaaS, this is not that. If you enjoy building systems where intelligence directly drives financial outcomes, this is a rare opportunity.
Who We Are
Recourse is being built in partnership with 25M Health, a healthtech venture firm. We have institutional backing, a shared platform team spanning engineering (full-stack, security, data science), strategy (fundraising, product, research), design (UI/UX, branding), and back-office (hiring, legal, accounting), and early access to large provider systems.
We’re actively working with health system design partners and have access to $400M+ in billable claims to inform product development from day one. This is a funded, validated opportunity with real customers and real data.
We’re small. We move quickly. We value clarity over theater.
We care deeply about clear thinking, high ownership, intellectual honesty, direct communication, and building durable systems. The early engineering decisions will define the company for years.
The Role
As Founding Head of Engineering, you will architect and build the core intelligence layer of the company. You will:
- Design the foundational data architecture across heterogeneous healthcare systems
- Define the modeling approach for expected value and win probability
- Lead production LLM integration for structured reasoning and document generation
- Build compliant, auditable workflows deeply integrated into provider systems and suitable for regulated environments
- Establish security posture — HIPAA, SOC 2 readiness, and data governance
- Recruit and lead a small, high-caliber engineering team
- Partner closely with us — including an experienced product leader with 15+ years scaling technology platforms in complex regulatory environments — on product strategy and long-term technical direction
This is a true 0→1 architecture role. You will write code, make structural decisions, and shape the engineering organization from the beginning. The output isn’t a dashboard. It’s real-world financial outcomes driven by intelligent systems.
Who You Are
You operate comfortably in ambiguity. You’ve designed systems where the data was messy, the rules evolved, and the stakes were real. You have the kind of urgency that’s quick and deliberate — not frantic. You know how to separate what must be done well now from what can be improved later, and you take initiative to make the whole team more effective.
You’re intellectually honest. When you don’t understand something, you keep digging until you do. When you’re wrong, you say so. In a domain as complex and messy as healthcare claims, that honesty is more valuable than false confidence.
You over-invest in communication — but to understand, not to convince. You translate fluently between engineering, product, and operations. You use clear language, not jargon, and you create space for others to push back on your ideas.
You’re resourceful. You see constraints as design challenges, not blockers. You leverage every resource at your disposal and take pride in doing more with less — because that’s what early-stage demands.
You put the team first. You’re reliable and fully invested. You know that sustainable intensity beats burnout, and you build a culture where people do their best work because they’re supported, not squeezed.
What You Bring
- 7+ years in software engineering, with 3–5+ years in senior technical leadership (Director, VP, or Head of Engineering)
- Experience building and scaling complex, data-intensive platforms from early stage through growth
- Strong architecture depth across workflow orchestration, ML-enabled systems, or high-volume transaction processing
- Experience deploying LLM-based features in production
- Hands-on technical depth — you still write code and review architecture while building a team
- Experience building in regulated or security-sensitive environments (HIPAA, SOC 2, financial controls, or similar)
- Experience hiring and leading small engineering teams
- Familiarity with healthcare data (claims, EDI, HL7/FHIR, clearinghouses) is a strong plus
Experience designing systems where correctness, auditability, and financial impact were tightly coupled is highly valued.
Sound judgment, technical depth, and ownership mindset are required.
Why This Role
This is a ground-floor opportunity to define the technical foundation of a new infrastructure layer in healthcare payments. You’ll apply AI to a real, high-stakes financial system. You’ll build durable systems, not short-term arbitrage. And you’ll do it with institutional backing while maintaining early-stage ownership.
If that combination is compelling, we’d like to talk.
Compensation
Base salary range: $200,000 to $225,000, with meaningful equity. Specific offers are calibrated to experience, location, and scope of the role. We also cover standard health, dental, and vision benefits, and expect our team to take real vacation time.
Equal Opportunity
Recourse is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law. We believe the best teams are built from people with different backgrounds and perspectives, and we're committed to creating an environment where everyone can do their best work.
Automatically Apply to the Best Remote Jobs
Stop the endless job search. Our AI finds and applies to the best jobs for you.
