Headway
Staff Software Engineer (Journeys)
$265K–$331K
Remote +3 · Remote · Staff · Full-time · Posted Aug 10, 2026
- Location
- Remote
San Francisco, CA
Seattle, WA
New York City - Experience
- 8+ years of software engineering experience, with meaningful time at Staff-level or equivalent.
About the job
Own the architecture and technical direction of Headway’s patient and provider communications platform, including its decision engine, experimentation layer, channel orchestration, and LLM-powered personalization.
What you'll do
- Design and evolve the communications decision engine, experimentation layer, channel orchestration, and unified message ledger.
- Set technical direction for a multi-vendor communications stack and bring LLM-powered personalization into production.
- Partner with marketing, CX, product, and patient teams to improve patient acquisition, retention, and health outcomes.
What they ask for
- 8+ years of software engineering experience, including meaningful time at Staff level or equivalent.
- Designed and built high-volume, event-driven communications platforms at millions of events per month.
- Experience with experimentation infrastructure such as A/B testing, engagement analytics, personalization, or recommendation systems.
- Exposure to LLM-powered systems in production, with attention to reliability, latency, and quality at scale.
Nice to have
- Fluency with multi-vendor delivery stacks and build-versus-buy trade-offs.
- Demonstrated ability to shape technical direction across teams without direct authority.
Pay
$265K – $331K USD base salary
Tools
Python 3, TypeScript, FastAPI, SQLAlchemy, React, Remix, Next.js, Postgres
AI focus
Build an agentic communications engine and bring LLM-powered personalization into production, with attention to reliability, latency, and quality at scale.
Model-written summary · the original posting is authoritative