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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Staff Software Engineer (Journeys) - **Company:** Headway, LLC - **Location:** Seattle, WA, United States (Remote available) - **Experience:** Expert - **Contract:** Permanent contract - **Skills:** A/B Testing, Application Programming Interfaces (APIs), Artificial Intelligence, Amazon Web Services, Amazon S3, Cloud Computing Security, Protocol Stack, Data Stores, Github, Python (Programming Language), PostgreSQL, Recommender Systems, Redis, Next.js, Software Engineering, SQLAlchemy, Twilio, TypeScript, Software Vulnerability Management, Datadog, ReactJS, Large Language Models, Apache Spark, Fastapi, Event Driven Architecture, Low Latency, Sentry, AWS Fargate, Apache Kafka, Software Version Control, Pagerduty - **Published:** August 15, 2026 - **Apply:** https://www.dice.com/job-detail/6537aead-6972-43c9-948e-799406daf8bf ## About the Role * We're looking for experienced engineers who have the ability to deal with ambiguity and learn new technologies and systems. Below are some additional experiences we think help engineers succeed at Headway. + 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 * Experience we're seeking + 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 ## Description * Languages: Python 3, TypeScript * Libraries & Frameworks: FastAPI, SQLAlchemy, React, Remix, Next.js * Datastores: Postgres, Redis * Infrastructure: AWS (Fargate, ECS, S3, and more), Spark and Kafka * Monitoring: Datadog, PagerDuty, Sentry * Version Control: Github, PagerDuty * Vulnerability Management: Snyk, Semgrep * Cloud Security: Lacework * Delivery: Knock (transactional + product notifications), Iterable (lifecycle marketing + campaigns), Twilio, Mailgun About the Journey Team at Headway * The Journey team powers how Headway reaches every patient and provider at the right moment, on the right channel - email, SMS and other communication channels. We're building the next chapter: an agentic communications engine that learns which message, which channel, and which timing works best for each person - and gets smarter with every send. We own the full stack: from the delivery layer (Knock for transactional, Iterable for lifecycle), to the decision engine we're building today., + 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. ## Related Videos - [Reducing LLM Calls with Vector Search Patterns - Raphael De Lio (Redis)](https://www.wearedevelopers.com/videos/1714-reducing-llm-calls-with-vector-search-patterns-raphael-de-lio-redis) - [From Doubt to Confidence: How Sentry Uses Verdaccio to Bulletproof SDK Releases](https://www.wearedevelopers.com/videos/739-from-doubt-to-confidence-how-sentry-uses-verdaccio-to-bulletproof-sdk-releases) - [20 billion requests a week: Upgrading Twilio's API gateway at scale](https://www.wearedevelopers.com/videos/100234-20-billion-requests-a-week-upgrading-twilio-s-api-gateway-at-scale) - [Coffee with Developers - Adam Wiggins](https://www.wearedevelopers.com/videos/919-coffee-with-developers-adam-wiggins) - [Accelerating Authentication Architecture: Taking Passwordless to the Next Level](https://www.wearedevelopers.com/videos/733-accelerating-authentication-architecture-taking-passwordless-to-the-next-level) - [Coffee with Developers](https://www.wearedevelopers.com/videos/354-coffee-with-developers) ## Related Articles - [Fully Remote Software Engineer Jobs](https://www.wearedevelopers.com/magazine/447-fully-remote-software-engineer-jobs) - [Dev Digest 121 - AI goes offline](https://www.wearedevelopers.com/magazine/456-dev-digest-121-ai-goes-offline) - [Dev Digest 120 - Apple and peers](https://www.wearedevelopers.com/magazine/455-dev-digest-120-apple-and-peers) - [Where To Find Software Engineering Jobs](https://www.wearedevelopers.com/magazine/396-where-to-find-software-engineering-jobs) - [How to Answer the Interview Question: “Why Do You Want to Be a Software Engineer?”](https://www.wearedevelopers.com/magazine/392-how-to-answer-the-interview-question-why-do-you-want-to-be-a-software-engineer) - [Navigating the AI Shift](https://www.wearedevelopers.com/magazine/629-navigating-the-ai-shift)