Senior IT Engineer (AI & Automation)

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!