Help 1,500 people at Automattic use AI tools exceptionally well. Not just “here’s how to use Claude”, but “here’s how to build custom agents for your workflow,” “here’s how to debug when Cursor gets stuck,” “here’s the skill I wrote that solves this exact problem you’re facing.”

This is developer advocacy turned inward. You’re embedded with Automattic's engineers, designers, and product teams, helping them level up their AI capabilities through hands-on teaching, tool development, and deep technical expertise. You’re technically experienced enough to build solutions yourself (scripts, agent skills, integrations, demos), but your superpower is translating that knowledge into practical help for others. You might also be an experienced software engineer with a passion for and experience in enabling others around you.

You’ll work in-person with our NYC AI team while supporting enablement efforts globally across Automattic’s distributed organization.

Why This Role Matters

Most companies treat AI adoption as “buy a license, send an email, hope people figure it out.”" That doesn’t work. Tools are powerful but rough. Workflows are unclear. People get stuck and give up.

You’ll ensure Automattic doesn’t waste the AI opportunity. Help engineers write better code faster, designers prototype ideas more efficiently, support teams resolve tickets more effectively, product teams make better decisions. Your leverage will be enormous: helping 1,500 people work 10% better compounds incredibly.

What You’ll Do

Run workshops and training sessions on AI tools (Claude Code, Cursor, emerging platforms); host office hours where people bring real problems and you solve them together.
Build Claude Project skills, custom agents, and scripts that make AI tools more useful for Automattic workflows.
Manage vendor relationships: work directly with AI tool providers to influence roadmaps, secure early access to features, troubleshoot enterprise adoption issues, and coordinate renewals and expansions.
Create practical enablement materials: video tutorials, written guides, example projects, and documentation that engineers and non-engineers can actually use.
Pair program with engineers to teach AI-assisted development workflows; help designers, PMs, and support teams adopt AI effectively.
Drive workflow transformation: identify where teams are stuck in old patterns, design adoption strategies that meet people where they are, turn skeptics into advocates through hands-on problem solving.
Stay deeply current on the AI tool landscape; experiment with emerging capabilities and share what works (and what doesn't).
Coordinate with our AI Enablement, Learn, and DevEx teams on education efforts; build internal community around AI best practices.

You’ll Thrive Here If You

Have 3-5+ years as a software engineer, developer advocate, or similar technical role. You’ve shipped code and helped others ship code.
Are proficient in at least one programming language (Python, JavaScript/TypeScript, PHP, or similar). You can build working demos and tools.
Live deep in the AI tools ecosystem. Beyond Claude, Cursor, and ChatGPT, you know the niche players, e.g. n8n for automation, specialized agents, emerging platforms most people haven’t heard of yet. You can recommend the right tool for any given scenario, not just the obvious ones.
Excel at teaching and communication. Comfortable running workshops, creating documentation, and helping people one-on-one.
Can translate technical concepts for diverse audiences, from engineers to designers to PMs.
Get more satisfaction from teaching than building alone. You’re energized by the “aha!”moment and want your impact multiplied through helping others.

Technical Experience We Value

Experience building with LLM APIs (OpenAI, Anthropic, etc.) and understanding prompt engineering, RAG, and applied AI techniques.
Previous software engineering, developer relations, developer advocacy, or technical education experience.
Track record creating technical content: blog posts, video tutorials, conference talks, or documentation.
Open source contributions or community building experience.
Understanding of multiple programming languages and development workflows.

Bonus Points

WordPress or PHP experience.
Experience building internal tools or developer productivity solutions.
Background in technical training or curriculum development.
Active presence in developer communities or AI tool ecosystems.
Have a deep software engineering background and care deeply about enabling others.

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 $150,000–$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 for high-caliber candidates with the skills and qualities to have a net positive for Automattic. Pay will reflect the potential contribution and the impact you can bring. #LI-DNI

About Automattic

Now in our 20th year, we’re the people behind WordPress.com, WooCommerce, Tumblr, Simplenote, Jetpack, Longreads, Day One, PocketCasts, Beeper, and more. We believe in making the web a better place.

We’re a distributed company with more than 1400 Automatticians in nearly every corner of the globe, speaking over a hundred different languages. Enriched by this diversity, we’re united by a singular mission: to democratize publishing, commerce, and messaging so anyone with a story can tell it, anyone with a product can sell it, and everyone can manage their communications from a single source. In short, we help maintain a balance in society, creating and continually refining powerful tools people can use to compete fairly—regardless of income, gender, politics, language, or where they live in the world.

We believe in Open Source, and the vast majority of our work is available under the GPL. Automattic is a Most Loved Company and Disability Confident Committed. (Here’s what that might mean for you.) Learn more about our dedication to diversity, equity, and inclusion and our Employee Resource Groups.

If you need disability-related accommodations during the application or interview process, please fill out this form. We are committed to ensuring an accessible hiring process for all candidates.

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All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran. View the ‘Know Your Rights: Workplace Discrimination is Illegal’ poster here. Automattic participates in the E-Verify program in certain locations, as required by law.

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