Staff Software Engineer (Journeys)

We’re looking for a Staff Engineer to be the technical anchor of the Journey team. This is a senior IC role — the person who owns the architecture of how Headway communicates at scale. You’ll design and evolve the decision engine, experimentation layer, and channel orchestration that will define how Headway reaches patients and providers for years to come. You’ll set the technical direction for a multi-vendor communications stack, own the unified message ledger, and bring LLM-powered personalization from concept to production. This role is high-leverage and cross-functional. You’ll work closely with marketing, CX, product, and the patient org — and your work will directly impact patient acquisition, retention, and health outcomes.

Responsibilities

Be the technical anchor of the Journey team; Own the architecture of how Headway communicates at scale; Design and evolve the decision engine, experimentation layer, and channel orchestration; Set the technical direction for a multi-vendor communications stack; Own the unified message ledger; Bring LLM-powered personalization from concept to production; Work closely with marketing, CX, product, and the patient org; Directly impact patient acquisition, retention, and health outcomes

Requirements

Ability to deal with ambiguity and learn new technologies and systems; 8+ years of software engineering experience, with meaningful time at Staff-level or equivalent; Designed and built high-volume, event-driven communications platforms (email, SMS, push, or equivalent) at millions of events per month; Fluency with multi-vendor delivery stacks, strong opinions about build-vs-buy trade-offs at the platform layer; Experience building or working closely with experimentation infrastructure (A/B testing, engagement analytics, personalization, or recommendation systems); Exposure to LLM-powered systems in production, not just API consumption, but thinking about reliability, latency, and quality at scale; Demonstrated ability to shape technical direction across teams without direct authority; Systems thinker who holds the architecture of a complex multi-vendor platform and guides the team through it; Engineer who has shipped high-throughput, event-driven systems in production and knows what reliability requires; Communicator who translates technical trade-offs for non-technical stakeholders and drives alignment across marketing, product, and engineering; Genuinely excited about the intersection of AI and communications, and thoughtful about what makes AI-in-the-loop systems reliable at scale; Leader who earns influence through technical depth and leaves teams more capable than they found them