Staff Software Engineer, Headway
Eng Foundations
$233-276k
Office located in New York, New York
Therapist-by-insurance marketplace
Be an early applicant
Therapist-by-insurance marketplace
1001+ employees
Be an early applicant
$233-276k
Office located in New York, New York
1001+ employees
Company mission
To build a new mental healthcare system, rewired for access and affordability.
Role
Who you are
- We’re looking for experienced engineers who have the ability to deal with ambiguity and learn new technologies and systems
- You have experience working across the stack on modern web applications
- Strong understanding of at least one programming language and comfortability with others
- Shaped work to achieve company and team goals
- Flexed into new technical and non-technical areas as projects require
- Committed team member supporting the growth of those around them
- Architected complex systems spanning multiple technical domains or product areas
- Driven technical vision and strategy at the organization level
- Established engineering standards and best practices across multiple teams
- Led major technical initiatives requiring coordination across multiple teams
- Mentored senior engineers and technical leaders
What the job involves
- 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!).
- 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
- 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
Application process
- Initial screen: You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background
- First round: You'll meet with an engineer on the team to do some live coding and learn more about the engineering team
- Final rounds: You’ll meet several more team members for technical and non-technical interviews and leave with a fuller picture of what it’s like to work at Headway
- References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!
Our take
1 in 4 US citizens are currently living with treatable mental health conditions, however, a vast majority of people are unable to access the care they need, the primary reason being cost. Headway connects clients with therapists who accept insurance as payment and provides independent practitioners with the tools and resources needed to serve their patients and manage administrative workloads.
Headway’s concept is timely, with national mental health under particular strain following events from the past few years. The company facilitates over 300,000 appointments per month and has attracted backing from the likes of Accel and Google Ventures.
Covering 16 states and the District of Columbia, the company intends to broaden its presence across the US using its 2023 Series C funding of $125 million. This is a crucial avenue for further growth, as medical care deserts across the US mean the potential market is vast.
Freddie
Company Specialist at Welcome to the Jungle
Insights
64% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Jul 2024
$100m
LATE VC
Oct 2023
$125m
SERIES C
Total funding: $327m
Company benefits
- Work from home opportunities
Company HQ
Tribeca, New York, NY
Leadership
Andrew Adams
(CEO)Worked as a Product Analyst at Spring, and was a Software Development Engineer Intern at Amazon.
Salary benchmarks
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