Head of Engineering

Own the platform. Own the deploys. Own the AI agent architecture. Turn HELIX from a founder-built system into production-grade infrastructure that 25 Medicare Advantage plans can run on without a single late-night page.

The mandate.

You will own full-stack development, deployment infrastructure, and AI agent architecture across HELIX. The platform is already in production at stars.nestedloop.ai. Your job is to scale it — to multi-plan tenancy, enterprise reliability, and the engineering culture that lets us ship daily without breaking trust.

Outcomes in your first year.

First 90 days

Take ownership of CI/CD, the daily smoke harness, and the deployment registry. Get to a place where production deploys happen without the founder in the loop. Define and publish engineering principles for the team you're about to build.

First 180 days

Ship the first multi-tenant deployment to a paying MA plan. Stand up SOC 2 Type I readiness. Hire your first 2 engineers. Reduce manual operational toil by 50%.

First 365 days

Run a 6–10 person engineering org. Three production MA plan deployments. SOC 2 Type II in flight. The platform is the reason customers renew.

About you.

You've shipped multi-tenant SaaS at production scale. Healthcare or another regulated, high-stakes domain is a meaningful plus.
You're hands-on with AI/agent system architecture — you've built with LLMs, retrieval, evaluation harnesses, not just integrated them.
Deep stack: TypeScript/Node, PostgreSQL, modern frontend. Comfortable owning infra (Railway, Vercel, Cloudflare) end-to-end.
You believe code review, test discipline, and on-call hygiene are non-negotiable — and you've built teams that practice them.
Bonus: prior CTO, VP Eng, or engineering lead at a healthcare or healthtech startup that reached $5M+ ARR.

Why this seat, right now.

HELIX is the AI operating system for Medicare Advantage. The first engineer after the founder owns the architectural decisions that define the next decade of the company. You'll work directly with the founder on the hardest problems and build the team that scales the system.

About HELIX

HELIX is the AI operating system for Medicare Advantage — a single intelligent surface where Stars, Risk Adjustment, and member engagement stop being silos and start being a system. The platform is built by Himanshu Arora, former Chief Data & Analytics Officer at Blue Cross Blue Shield of Massachusetts, and advised by Sandra Clarke, former EVP & COO of Blue Shield of California ($25B revenue, 4.8M members).

We are early-stage and well-funded enough to hire senior. Compensation is competitive for stage and includes meaningful equity. Specifics shared in conversation.

Want to be considered when we open this role?

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