Senior IT Engineer; AI & Automation

Position: Senior IT Engineer (AI & Automation)
New York, New York, United States;
San Francisco, California, United States;
Seattle, Washington, United States

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 60,000 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 the role:

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide. The IT team at Headway is an essential function at Headway that builds operational efficiency into everything we do, giving our organization the tools needed to achieve our goals of reshaping mental healthcare. In this role, you’ll have the unique opportunity to build the foundations of productivity engineering at Headway, including the implementation of AI and automation to enable efficiency across our organization.

You’ll love this role if you want to:

• Use AI, LLMs, and agentic automation to solve meaningful operational problems across the company.

• Architect and ship scalable workflows while exploring new technologies such as AI.

• Enjoy building internal tools from scratch, not just configuring out-of-the-box features.

• Care about reliability—adding observability, structured error handling, and testing frameworks so automations behave like production software.

• Create reusable frameworks, templates, and patterns so future workflows can be built faster and more consistently—not one-off scripts.

• Collaborate closely with internal teams to understand needs and translate them into solutions that materially increase speed and efficiency.

• Think in systems, not tasks—and design foundations that scale as the company grows.

You may be a good fit if you:

• Architect, build, and deploy scalable workflow automations and integrations across core business systems using AI/LLMs and agentic automation.

• Design, build, and maintain custom internal tools leveraging APIs and cross-platform automation tools.

• Implement error handling and observability for automations and internal tools.

• Develop automation templates/standards and frameworks that enable future workflows to be created rapidly and with consistency.

• Develop testing frameworks for automated workflows to ensure quality, reliability, and resilience.

• Develop longitudinal relationships across Headway and partner with stakeholders to design and implement automated solutions to enable Headway teams to work with speed.

Tools we use:

• Identity and Access Management:
Okta, Lumos

• Email and Messaging:
Gmail and Slack

• Document Creation and

Collaboration:

Google Workspace, Confluence

• Credential Management: 1

Password

• Project Planning:
Jira

After you apply to Headway, here are some details of what to expect during the interview 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  meet with the IT Manager to discuss your previous experience, and do an initial technical screen.

• Final rounds:
You’ll meet several team members for technical and non-technical interviews, and leave with a fuller picture of what it’s like to work at Headway.

•…