Enterprise Migrations Engineer

👋 A LITTLE ABOUT US

We’re building the best platform for authoring, publishing, and maintaining world-class docs. Close to 40,000 sign-ups per month, over 100k Monthly Active Users, used by 2M+ people and thousands of teams like Zoom, FedEx, Nvidia, Snyk, and Google. We’re profitable, backed by P9 Capital, Notion Capital, and Fly VC, and our amazing team is spread across 15 countries in North America, Europe, and Asia.

We're winning more enterprise deals, and those enterprises come with a lot of existing documentation — sometimes hundreds of thousands of pages spread across legacy wikis, PDFs, RST files, HTML exports, and formats we've never encountered before. When they sign with us, we need to get all of that into GitBook cleanly, quickly, and reliably.

This is a new function at GitBook. You'd be the first person to own it.

WHAT YOU'LL DO

• Own enterprise content migrations end-to-end: scoping, customer communication, execution, and delivery
• Work directly with customers to understand their content structure and set accurate expectations
• Write and run transformation scripts to parse, normalize, and import content from a wide range of source formats — PDF, HTML, RST, Confluence exports, custom CMS dumps, and whatever else turns up
• Build reusable tooling and pipelines so each migration is faster than the last
• Define the migration process as you go, turning one-off work into a documented, repeatable playbook
• Partner with Solutions Engineers pre-sale to scope migration complexity and inform deal strategy
• Feed product feedback based on what you see in the field — you'll have strong opinions about what GitBook should handle natively

TECHNICAL ENVIRONMENT

You'll work primarily with:

• Python for transformation scripts and automation
• GitBook's API and Git Sync for content ingestion and structuring
• Common document formats: Markdown, RST, HTML, XML, PDF (text extraction), Confluence XML exports
• Standard tooling: shell scripting, Git, basic data wrangling

We don't mandate a specific stack beyond what's needed to get migrations done reliably. If you have a better tool for a job, use it.

WHAT WE'RE LOOKING FOR

Ownership mindset. This role has no established playbook. You'll be writing one. That means defining the process, flagging problems early, and not waiting to be told what to build next.

Technical depth in document formats. You're comfortable parsing and transforming messy, structured, and semi-structured content at scale. You know when to write a custom parser and when off-the-shelf tools are good enough.

Customer-facing credibility. You'll be on calls with enterprise customers, explaining complexity, managing timelines, and occasionally delivering news they don't want to hear. You can do that clearly and without drama.

Low tolerance for doing the same thing twice. The point of this role isn't just to run migrations — it's to make migrations systematically faster. Every project should leave behind something reusable.

Pragmatism. The goal is clean content in GitBook, not perfect code. You know the difference between a script that ships this week and one that ships next quarter.

WHAT THIS ROLE IS NOT

This isn't a role where you'll be managing a team or setting product strategy from day one. It's not a pure software engineering position, and it's not primarily a customer success or account management role. It sits between those things: technical enough that code quality and systems thinking define what's possible, customer-facing enough that communication and reliability matter equally.

If you do this well, the function grows in scope, tooling, and eventually headcount. But we're hiring for someone who wants to build it from scratch — not for the version of this role that exists in two years.

IDEAL BACKGROUND

You might be coming from a technical writing or documentation engineering background, a solutions engineering role that got heavier on the scripting side, a data engineering role where the data just happened to be documents, or somewhere else entirely. We care less about the label than about what you can actually do.

Helpful but not required: experience with content management systems, structured content formats (DITA, DocBook, etc.), or prior work at a developer tools or documentation company.

HIRING PROCESS

1. Intro screening — 30 minutes with our Head of People to cover your background and the role
2. Deep dive — 45 minutes with our Head of Sales & Solutions Engineering
3. Technical exercise — a 60-minute session where you'll present your approach to a realistic migration scenario, with our Solutions Engineering and Account Management teams
4. Final round — 30 minutes with our CEO

👥 Join GitBook at a pivotal time as we evolve our product and team.