Staff Software Engineer (Journeys)

About the Position

Staff Software Engineer (Journeys)

We are looking for a Staff Software Engineer to join our Journeys team at Headway. This is a senior individual contributor role where you will be the technical anchor, designing and evolving the decision engine, experimentation layer, and channel orchestration that will define how Headway reaches patients and providers for years to come.

Location

• Remote
• New York City
• San Francisco, CA
• Seattle, WA

Employment Type

Full time

Compensation

• $265K - $331K

About the 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.

Responsibilities

• 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.

Requirements

• 8+ years of software engineering experience, with meaningful time at Staff-level or equivalent.
• Designed and built high-volume, event-driven communications platforms.
• 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.
• Exposure to LLM-powered systems in production.
• Demonstrated ability to shape technical direction across teams without direct authority.

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, Kafka
• Monitoring: Datadog, PagerDuty, Sentry
• Version Control: Github
• 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 Headway

Headway’s mission is to fix the mental healthcare system by building a new 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.

We Offer

• Competitive salary
• Comprehensive health and wellness benefits
• Retirement savings
• Meaningful ownership opportunities through equity

About the Company

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 to receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

Headway participates in E-Verify. To learn more, click here.

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.