Principles that guide us
Focus on the mission: We view software as a means of effecting change in the world, not as an end unto itself. We write software to empower our patients and therapists to better solve the problems they’re facing.
Ship small, learn fast: We are building new and novel products and believe that we learn what our users need by quickly shipping and iteration
Everything is a product: Whether it’s our patient search experience or a developer productivity improvement, we treat everything we build at Headway as a product with end-users in mind.
Optimize for trust: We believe that engineers should be continually learning. To learn effectively and to be productive, engineers must feel safe asking questions and discussing mistakes.
Tools we use
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.
About this role
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.
Who you are
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
Comprehensive benefits
Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave.
We believe a team’s strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.
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A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.
