Staff Software Engineer (Journeys)
About The Position
Headway's mission is to fix the mental healthcare system by making it accessible to everyone, starting with solving the insurance barrier. Over 75,000 providers use their software, serving over 1 million patients. They are building tools for therapists, improving the process of finding a therapist, and investing in platform foundations for scale. Headway is a Series D company with over $325M in funding, seeking exceptional individuals to help achieve their mission and provide a meaningful career experience. The engineering team at Headway uses technology to build a new mental healthcare system. Their guiding principles include focusing on the mission, shipping small and learning fast, treating everything as a product, and optimizing for trust to foster continuous learning and a safe environment for asking questions and discussing mistakes. They use languages like Python 3 and TypeScript, with frameworks such as FastAPI, SQLAlchemy, React, Remix, and Next.js. Their datastores include Postgres and Redis, and they utilize AWS infrastructure, Spark, Kafka, Datadog, PagerDuty, Sentry, Github, Snyk, Semgrep, and Lacework for their tools and infrastructure.
Requirements
- 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 (reliability, latency, and quality at scale).
- Ability to deal with ambiguity and learn new technologies and systems.
- A systems thinker who holds the architecture of a complex, multi-vendor platform and guides the team through it.
- An engineer who has shipped high-throughput, event-driven systems in production and knows what reliability requires.
- A 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.
- A leader who earns influence through technical depth and leaves teams more capable than they found them.
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.
- Shape technical direction across teams without direct authority.
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
