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 : 1Password

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\u2019ll 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\u2019ll 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

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 Custom Demographic Questions

We believe that to build the best startup team, we must build a diverse, equitable and inclusive team. We encourage people from all backgrounds to apply to all roles, and we proactively work to design hiring processes that mitigates bias. To help us track the parity in our candidate pipelines and efficacy of our recruiting efforts, please consider answering the following demographic questions. While completion of this survey is required, you will have the option to select "I don\u2019t wish to answer" for all questions. Your responses will be used (in aggregate only) to help us identify areas of improvement in our process. Your responses will not be linked to your specific application and will not in any way be used in the hiring decision.

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

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