Staff Software Engineer (Journeys)

Headway; United States; On-site; USD 265,000 - 331,000; Full time

Job summary

Headway is seeking a Staff Engineer to be the technical anchor of the Journey team. This senior IC will own the architecture of how Headway communicates at scale, design 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 stack and bring LLM-powered personalization to production.

Qualifications

• 8+ years of software engineering experience at staff level or equivalent.
• Built high-volume, event-driven communications platforms.
• Experience with multi-vendor delivery stacks and platform trade-offs.
• Experience with experimentation infrastructure and AI-in-the-loop systems.

Responsibilities

• Own architecture of Headway communications at scale.
• Design and evolve the decision engine, experimentation layer, and channel orchestration.
• Set technical direction for a multi-vendor stack and unified message ledger.
• Collaborate with marketing, product, and CX to impact patient acquisition and retention.

Skills

Staff-level experience

Event-driven systems

Multi-vendor stacks

Experimentation

LLM in production

Technical leadership

Tools

Knock

Iterable

Twilio

Mailgun

Job description

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

About Engineering At Headway

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide. The engineering team at Headway is a small but mighty team using technology to build that future (and have a fun time while doing it!).

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

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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Compensation Range: $265K - $331K