Staff Engineer, Journeys — AI Messaging at Scale

Headway; United States; On-site; USD 265,000 - 331,000; Full time

Job summary

Headway is seeking a Staff Engineer to anchor the Journey team's communications stack and own the architecture for scalable, multi-channel messaging. You’ll design and evolve the decision engine, experimentation layer, and channel orchestration that define how Headway reaches patients and providers at scale.

You’ll collaborate with marketing, CX, product, and the patient org to drive patient acquisition, retention, and health outcomes while delivering reliable, high-throughput systems powered by

Qualifications

• 8+ years of software engineering experience at staff level or equivalent.
• Designed and built high-volume, event-driven communications platforms across multiple channels.
• Experience with multi-vendor delivery stacks and build-vs-buy trade-offs at the platform layer.
• Experience with experimentation infrastructure, A/B testing, analytics, personalization, or recommendations.
• Exposure to LLM-powered systems in production, focusing on reliability and latency.

Responsibilities

• Own the architecture of Headway's communications at scale and define the decision engine, experimentation layer, and channel orchestration.
• Set technical direction for a multi-vendor communications stack and the unified message ledger.
• Bring LLM-powered personalization from concept to production.
• Collaborate cross-functionally with marketing, CX, product, and the patient org to impact acquisition, retention, and health outcomes.

Skills

Systems thinker

Event-driven systems

Multi-vendor delivery stacks

Communication with stakeholders

AI in communications

Technical leadership

Staff-level experience

Reliability at scale

Tools

Python

TypeScript

FastAPI

SQLAlchemy

React

Job description

Headway is seeking a Staff Engineer to anchor the Journey team's communications stack and own the architecture for scalable, multi-channel messaging. You’ll design and evolve the decision engine, experimentation layer, and channel orchestration that define how Headway reaches patients and providers at scale.

You’ll collaborate with marketing, CX, product, and the patient org to drive patient acquisition, retention, and health outcomes while delivering reliable, high-throughput systems powered by