Staff Software Engineer (Journeys)
Headway.co · USA
About this role
## About Headway Headway’s mission is to make mental healthcare accessible for everyone. In the US, 1 in 4 people have a treatable mental health condition, but many providers don’t accept insurance—making therapy too expensive for most people. Headway is building the next-generation mental healthcare system by solving the biggest barrier to care (insurance) and expanding into a full platform where care actually happens. ## Engineering Principles - **Focus on the mission**: Software as a means of effecting change. - **Ship small, learn fast**: Build new products and iterate quickly. - **Everything is a product**: Treat every effort as user-facing. - **Optimize for trust**: Create an environment where engineers can learn safely. ## Tech Stack (examples) - **Languages**: Python 3, TypeScript - **Frameworks/Libraries**: FastAPI, SQLAlchemy, React, Remix, Next.js - **Datastores**: Postgres, Redis - **Infrastructure**: AWS (Fargate, ECS, S3, etc.), Spark, Kafka - **Monitoring**: Datadog, PagerDuty, Sentry - **Version Control**: GitHub, PagerDuty - **Security/Vuln Mgmt**: Snyk, Semgrep - **Cloud Security**: Lacework - **Delivery/Notifications**: Knock, Iterable, Twilio, Mailgun ## About the Journey Team The **Journey** team powers how Headway reaches patients and providers at the right moment, on the right channel (email, SMS, and more). You’ll help build an **agentic communications engine** that learns which message, channel, and timing works best for each person—and improves with every send. ## Role: Staff Software Engineer (Journeys) This is a **senior IC** role and the **technical anchor** for the Journey team. You will: - Own the **architecture** for how Headway communicates at scale - Design and evolve the **decision engine**, **experimentation layer**, and **channel orchestration** - Set technical direction for a **multi-vendor communications stack** - Own the **unified message ledger** - Bring **LLM-powered personalization** from concept to production - Partner cross-functionally with **marketing, CX, product, and the patient org** to impact acquisition, retention, and health outcomes ## Who You Are You’re an experienced engineer who can thrive in ambiguity and learn new systems quickly. You likely have: - Strong systems thinking and the ability to guide architecture for complex, multi-vendor platforms - Experience shipping **high-throughput, event-driven** systems with a focus on reliability - The ability to translate technical trade-offs for non-technical stakeholders and drive alignment - Genuine excitement for the intersection of **AI and communications**, with thoughtful reliability considerations for AI-in-the-loop systems - Leadership through technical depth—leaving teams more capable than you found them ## Experience We’re Seeking - **8+ years** of software engineering experience, including meaningful time at **Staff-level (or equivalent)** - Built high-volume, event-driven communications platforms (email/SMS/push or similar) at **millions of events/month** - Fluency with **multi-vendor delivery stacks** and strong opinions on **build vs. buy** at the platform layer - Experience with **experimentation infrastructure** (A/B testing, engagement analytics, personalization/recommendations) - Exposure to **LLM-powered systems in production** (reliability, latency, and quality at scale) - Demonstrated ability to shape technical direction across teams without direct authority ## Benefits (highlights) - Medical, dental, visio
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