Applied AI Engineer, Internal Tooling

Applied AI Engineer, Internal Tooling - New York

Remote

Location:

NYC No

Ho Office (5 days a week)

Build the AI tools that Automattic uses internally. Maintain and extend Libre Chat, our self-hosted AI interface. Create lightweight integrations and automations that make teams more productive. Help 1,500 people work better with AI.

This isn’t about building consumer products or shipping to millions of users. It’s about building tools for the people sitting next to you, getting immediate feedback, and iterating based on what actually helps. If you’ve ever wished you could control your own AI tools, customize them exactly how you want, and not be at the mercy of third-party vendors, this is that opportunity.

You’ll work in-person with our NYC AI team while your tools serve Automattic’s distributed organization globally.

Most companies are locked into third-party AI tools:
ChatGPT, Claude, whatever comes next. They’re stuck with whatever features the vendor ships, whatever privacy terms are imposed, and whatever prices are charged.

Automattic wants to control our AI infrastructure, customize it for our needs, and build tools that make our specific workflows better. You’ll have unusual freedom: self-hosted and open source stack, users sitting next to you with immediate feedback, no enterprise procurement cycles. Making 1,500 people more productive compounds quickly, and your work will improve Libre Chat for everyone.

• Own Automattic’s Libre Chat deployment: maintain, extend, and customize our self-hosted AI interface (Type Script/Node.js stack).
• Contribute upstream to the Libre Chat open source project; add features specific to Automattic’s needs while improving the project for everyone.
• Build lightweight internal tools and automations that help teams use AI better; integrate AI capabilities into existing Automattic systems.
• Work with Dev Ops on hosting, scaling, and reliability; debug issues, triage user feedback, ship improvements continuously.
• Create agent skills, custom workflows, and productivity multipliers; experiment with emerging AI tools, and prototype new capabilities.
• Document what you build so others can use it effectively; run workshops and office hours to help engineers adopt AI tooling.

• Are comfortable contributing to open source projects.
• Actually use AI tools in your workflow. Through your own direct experience, you understand what makes such tools useful or frustrating.
• Can work independently. You’ll be the first engineer focused on internal AI tooling; you need to be self-directed.
• Communicate clearly. You document what you build and help non-technical people use it effectively.
• Want to see your work used immediately by real people and prefer iterating with users next to you.

• Dev Ops experience:
  Docker, self-hosted infrastructure, Kubernetes, and managing production services.
• Previous work on developer tools, internal platforms, or productivity software.
• Open source contributions beyond Libre Chat; track record of upstream engagement.
• Understanding of LLM APIs (OpenAI, Anthropic, etc.) and how to build with them.
• Experience with Python for quick prototyping and AI integrations.

• Background in developer relations or technical advocacy.
• Experience building tools for distributed teams or remote-first organizations.
• Understanding of Word Press or PHP.
• Track record of building internal tools that became critical company infrastructure.

At Automattic, we use global salary ranges that do not vary by location. However, because this role is required to be based in our New York City office 5 days a week, we have applied an adjustment to the global band to support additional costs associated with the office-based role requirements. The salary for this role is $170,000–$230,000 USD.

If you later move to a different team or role at Automattic that is not NYC office‑based, your salary would be adjusted to the applicable global pay band for that role, which could result in a reduction in salary. Note that the global range would apply even if your chosen location of residence is NYC.

We are searching…