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. Building and maintaining systems to enable efficiency across our organization through the implementation of AI and Automation.

You’ll love this role if you want to:

Use AL, LLMs, and agentic automation to solve meaningful operational problems across the company.
You get energy from architecting and shipping scalable workflows while diving into new technologies such as AI.
You enjoy building internal tools from scratch, not just configuring out-of-the-box features.
You care about reliability—adding observability, structured error handling, and testing frameworks so automations behave like production software.
You want to create reusable frameworks, templates, and patterns so future workflows can be built faster and more consistently—not one-off scripts.
You love partnering closely with internal teams to understand their needs and translate them into solutions that materially increase speed and efficiency.
You think in systems, not tasks—and want to 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:

AI Tools: Gemini, Glean, Slack AI, Atlassian Intelligence
Identity and Access Management: Okta, Lumos
Email and Messaging: Gmail and Slack
Document Creation and Collaboration: Google Workspace, Confluence
Credential Management: 1Password
Ticketing: Jira Service Desk, ZenDesk, Jira Projects
Project Planning: Jira
Endpoint Management: JAMF, InTune, ChromeOS, Kolide

Our interview process

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'll 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.
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!

The expected base pay range for this position is $152,150 - $179,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance-based variable compensation and an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

Equity compensation
Medical, Dental, and Vision coverage
HSA / FSA
401K
Work-from-Home Stipend
Therapy Reimbursement
16-week parental leave for eligible employees
Carrot Fertility annual reimbursement and membership
13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
Flexible PTO
Employee Assistance Program (EAP)
Training and professional development

#LI-EM1

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.

Headway employees work remotely across the US, with the option to work from offices in New York City, San Francisco and Seattle. Headway participates in E-Verify. To learn more, click here.

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

Senior IT Engineer (AI & Automation)

You may be a good fit if you:

Related Jobs

Senior UX Designer

Technical Support Associate, EMEA (German Speaking)

IT Support Technician

Solutions Integration Enginer III

Senior Program Manager, Sales Engineering (Operations)

Financial Systems Analyst

Technical Support Analyst

Technical Support Analyst

Principal Analyst - People Technology ( Comp & Benefits)

Financial Systems Senior Project Manager