Documentation Engineer

The Role

We need a Documentation Engineer to own all technical content across Scaleout, Scaleup, and Orchestration — and to pitch in across the Customer Experience (CX) team wherever you're needed most.

This is a multi-hat role at a startup. Your primary mandate is building and running a documentation pipeline that uses AI tools (Claude, Cursor) and automation to produce, verify, and maintain technical content at a pace that keeps up with the product. But you're also a working member of a small team. Depending on where we are in a release cycle, your week might look very different:

• During a release push: You're heads-down on docs. Drafting, verifying CLI outputs on live switches, coordinating with engineering on accuracy, pushing content through review.
• Between releases: You're helping in the lab, assisting with customer cases, supporting professional services engagements, building training materials, or working on automation that makes the next release cycle faster.

The common thread is that you're technical enough to do real engineering work, you write well enough to produce publication-grade content, and you use AI tools as a force multiplier for both. When a doc says "run this command and expect this output," you've already run it yourself and confirmed it. When you find a mismatch between documentation and product behavior, you file the bug.

You're expected to be proficient with AI tools from day one. Claude and Cursor are your primary tools for drafting, formatting, style enforcement, command verification, and content generation. This is not "AI-assisted" as a nice-to-have. It's how the work gets done.

Documentation Pipeline

• Build and operate AI-driven workflows for documentation production: draft generation from source code and PRDs, style enforcement, terminology consistency, command verification against live switches, and release note generation.
• Develop and maintain Claude skills and prompts that enforce consistent structure and formatting across all documents.
• Establish document control standards: numbering, revision tracking, cross-references, and change management.
• Use Cursor to extract technical context from source code repositories, verify documented behavior against actual implementation, and identify undocumented features or changes.

Product Documentation

• Own all technical documentation across Scaleout, Scaleup, and Orchestration: installation guides, configuration references, troubleshooting procedures, hardware guides, API documentation.
• Generate content from engineering input, source code, PRDs, and your own hands-on testing. Not just formatting — creating.
• File bugs when documentation verification reveals product issues. If the documented behavior doesn't match the actual behavior, that's a bug and you own reporting it.
• Work with engineering and product teams to document new features, APIs, integrations, and architecture.

Team Training and Enablement

• Develop training materials for new product features, common support scenarios, and operational procedures.
• Deliver training to the support team — formal sessions for new releases, informal walkthroughs on cases.
• Turn recurring ticket patterns into documented procedures and training content.
• Help onboard new team members with product knowledge and tooling.

Security Responses and Incident Content

• Write security response documents (SIRTs) that are clear, accurate, and scoped for the right audience.
• Make sure remediation steps are technically correct and actionable.
• Standardize incident communication format and process.

Release Communications

• Write release notes that explain engineering changes in language customers can act on.
• Work with product and engineering to make sure every release is documented before it ships.

Customer-Facing Content Oversight

• Final review on anything customer-facing: KB articles, presentations, UI copy, email templates.
• Review content from other teams for clarity, accuracy, and consistency.

Team Support (as needed)

• Assist with customer cases during escalations or capacity constraints.
• Support lab work: test setups, configuration verification, reproduction of customer-reported issues.
• Contribute to professional services engagements where documentation, training, or technical content is needed.
• Step into any role on the CX team where an extra set of capable hands is needed.

Requirements:

• 5+ years in a hands-on technical role: technical support engineering, solutions engineering, field engineering, network engineering, or similar. You've worked real issues on real infrastructure, not just written about them.
• Direct experience with networking infrastructure: data center switching, network operating systems (SONiC strongly preferred), routing protocols, CLI-based troubleshooting. You can read a show command output and know what's wrong.
• Strong, clear writing skills. You don't need a technical writing background, but your written communication — case notes, internal docs, customer emails, runbooks — is consistently well-organized and easy to follow. Bring samples.
• Hands-on, daily use of AI tools (Claude, Cursor, or similar). Not "interested in AI" — actively using it to produce work. You should be able to demonstrate how you use AI to draft content, verify technical claims, or automate repetitive tasks.
• Self-directed. You chase down answers — you don't wait for someone to hand you a spec. If the engineer is busy, you read the code. If the doc is unclear, you test it yourself. If the process is manual, you automate it.
• Comfortable working in Git. You'll work with source code repositories to extract technical context and manage documentation as code.
• Comfortable presenting and training. You can stand in front of a team and explain something technical clearly, whether that's a Zoom walkthrough or a hands-on lab session.:
• Experience writing customer-facing documentation (KB articles, runbooks, troubleshooting guides, installation procedures).
• Experience building automation workflows (scripted processes, CI/CD pipelines, AI agent workflows).
• Background in cybersecurity or experience supporting security-focused products.
• Familiarity with docs-as-code workflows (Markdown, static site generators, CI/CD for docs).
• Familiarity with API documentation tools (Swagger/OpenAPI, Postman, ReadMe).
• Prior experience developing and delivering technical training.

Why This Role Matters

Our customers run critical infrastructure on our products. When the docs are wrong, customers hit problems. When the docs are missing, customers can't self-serve and the support team absorbs the load. When the team isn't trained on new features, escalations stack up. This role exists to close those gaps — not by writing docs one at a time, but by building the systems and workflows that keep documentation accurate, current, and scalable as the product grows.

Growth Path

This is an individual contributor role today. As UpscaleAI grows, the documentation and enablement function will expand. The person in this role would be the natural choice to shape that team and define how it's built.