Senior Software Engineer

CTO Opportunity At Clearest Health

This role reports directly to the CEO and is intended to promote to CTO. We move fast: ex-founders and operators can join us within a single day of meeting. If you're looking for that level of urgency, ownership, and trust, you'll feel at home here.

I previously built LLM systems at Amazon and wanted to find a market where I was the only, not the best (thanks PT). And I found it. I infiltrated health insurance companies to learn how they work and saw the massive inefficiency in how doctors get paid for out-of-network care. Clearest Health exists to fix that with data and automation that didn't exist before.

Healthcare payments is one of the largest, most broken markets in the world. It's a $300B+ industry that runs on outdated systems and painful manual work. Providers lose billions every year, and fixing it requires LLMs that can scale where humans can't.

I was looking for a market where we can compete at the service layer, use AI internally rather than vend it for immediate iteration loops, and generate revenue in a massive market. Well, this is it!

We've built the foundation and secured partnerships with the three largest law firms in the country. We're now preparing to deploy across 200 provider groups. The demand is here, the market is massive, and the opportunity to shape the future of healthcare payments is wide open.

This is a true ground-floor role: you'll be writing code that powers billions of dollars in cashflow for hospitals and physician groups, while shaping the product and culture of the company from day one.

Expect your friends to ask why you're working so hard — and then ask if they can join. (intentional, non-AI em dash btw)

First 30 days: Ship the LLM-first, automated dispute-tracking pipeline that our top 3 law firm partners depend on. You'll own it end-to-end: data ingestion, status updates, and the provider-facing dashboard.

First 60 days: Take over the eligibility engine and benchmark infrastructure backed by 1.8M verified IDR pricing records. Redesign the data pipeline to handle deployment across 200 provider groups.

First 90 days: Lead architecture decisions across the platform. Begin building and managing the engineering team (on/offshore). You're operating as de facto CTO.

Role requirements:

• 4+ years of professional software engineering experience
• Full-stack experience with ownership of features end-to-end

Culture-fit requirements:

• Customer-obsessed: care deeply about solving real problems for providers
• Opinionated but convincible: strong views, open to better ideas
• Great taste: in design, code, and product judgment
• Wicked fast iterations: bias toward action and rapid learning
• High trust, high loyalty: thrives in high-autonomy, high-accountability environments
• Mission-driven: passionate about changing healthcare economics

Role guidelines:

• Measure twice, cut once: design features by presenting multiple options before building
• High ownership: run independently and own features end-to-end with minimal guidance
• Comfort with speed: willing to take shortcuts when strategically directed
• Super user: cursor, Claude Code, Vercel, etc.
• Team-builder: help manage and grow an on/offshore team as we scale
• Greenfield builder: design and build products from repo creation
• Data-heavy expertise: skilled at building data-intensive applications
• Bonus: background in life sciences, UX, or product design

Technical stack:

Frontend

• React + React Router for the provider-facing platform (claims management, analytics dashboards, dispute tracking)
• Tailwind CSS + ShadCN/Mantine component library
• Real-time data visualization for revenue gap analysis and CPT code benchmarking

Backend

• Node.js + TypeScript on Hono (runs on Lambda) for APIs and business logic
• Go for high-throughput I/O: data pipelines, batch processing, RPA automation
• LLM integration (Claude, GPT-4) for AI-generated dispute documentation and eligibility engines
• RAG architectures, prompt engineering, and hallucination detection for legally significant document generation

Infrastructure

• AWS end-to-end: Lambda, ECS Fargate, S3, DynamoDB, PostgreSQL
• Cloudflare Pages for static hosting
• Auth via Clerk (migrating to Auth.js)
• CloudWatch + Metabase for observability and analytics
• HIPAA-compliant architecture: encryption at rest/in transit, PHI access controls, audit logging