Staff Software Engineer- Eng Foundations

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 

1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. 

Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 45,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.

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

Projects we’re working on:

At Headway, we treat infrastructure and developer experience as force multipliers. Here’s a look at the core engineering initiatives that enable us to move fast, deliver reliably, and scale responsibly:

• Platform Architecture & Scalability: Modularize the backend (Mamba) to enable pod-level autonomy via clear ownership boundaries, standardized observability, and scalable infrastructure patterns.
  
  
• Developer Experience & Agentic Tooling: Build agentic tooling and abstractions to eliminate low-leverage tasks (e.g., smart test generation, scaffolders, code-aware search), improve CI/CD velocity and stability, surface actionable metrics (e.g., PR throughput, review latency), and standardize local environments and dev scaffolding.
  
  
• Web Platform & UI Architecture: Standardize all core web apps on a unified stack (e.g., Headway design system, Remix), scale adoption of shared components and testing patterns (unit, integration, E2E), simplify state management and architecture, and enforce performance, accessibility, and security standards.
  
  
• Observability & Quality: Expand proactive observability through SLOs, dashboards, and structured alerts, integrate real user monitoring (RUM), and link telemetry with test coverage to prioritize reliability improvements based on user impact.
  
  
• Communications Platform: Empower product teams to own and experiment with customer messaging via event-based workflows and reusable compliant templates for email, SMS, and secure messaging.

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.

For all engineers:

• You have experience working across the stack on modern web applications
• Strong understanding of at least one programm