Documentation Engineer

Upscale, Inc. • Headquarters, KY

4d • $160,000 - $220,000

About The Position

Upscale, Inc. is hiring a Documentation Engineer to own technical content across its Scaleout, Scaleup, and Orchestration products while also supporting the Customer Experience (CX) team as needed. The role’s primary focus is building and operating an AI-driven documentation pipeline that uses tools such as Claude and Cursor, along with automation, to produce, verify, and maintain technical content in step with product releases. The position requires hands-on technical work: verifying documented commands on live switches, checking documentation against product behavior, coordinating with engineering on accuracy, and reporting bugs when behavior and documentation do not match.

Work varies with the release cycle. During release pushes, the engineer drafts and verifies documentation, coordinates reviews, and prepares release content. Between releases, the engineer may assist in the lab, help with customer cases and professional services engagements, create training materials, or improve automation. The role combines technical infrastructure experience, publication-quality writing, and practical use of AI tools.

The engineer owns product documentation such as installation guides, configuration references, troubleshooting procedures, hardware guides, and API documentation. They build workflows for drafting content from source code and product requirements documents (PRDs), style and terminology enforcement, command verification, and release-note generation. They also maintain Claude skills and prompts; establish document-control standards; and use Cursor and Git repositories to gather technical context, verify behavior, and identify undocumented features or changes.

The role also includes creating and delivering training for support staff, writing security incident response documents (SIRTs), preparing customer-actionable release notes, and reviewing customer-facing content such as knowledge-base articles, presentations, UI copy, and email templates. As needed, the engineer helps with escalated customer cases, lab testing and issue reproduction, professional services, and other CX team work.

This is an individual-contributor role today, with the opportunity to shape the documentation and enablement function as the company grows. The listed annual salary range is $160,000–$220,000, depending on experience, skills, and impact.

Requirements

• At least 5 years in a hands-on technical role such as technical support engineering, solutions engineering, field engineering, or network engineering.
• Direct experience with networking infrastructure, including data center switching, network operating systems (SONiC strongly preferred), routing protocols, and CLI-based troubleshooting.
• Strong, clear writing skills; written communication such as case notes, internal documentation, customer emails, and runbooks should be consistently well organized and easy to follow. Applicants should bring writing samples.
• Daily hands-on use of AI tools such as Claude, Cursor, or similar, with the ability to demonstrate how they are used to draft content, verify technical claims, or automate repetitive tasks.
• Self-directed approach to finding answers, testing unclear documentation, reading code when needed, and automating manual processes.
• Comfort working in Git and with source-code repositories to extract technical context and manage documentation as code.
• Ability to present and deliver technical training clearly, including Zoom walkthroughs and hands-on lab sessions.

Nice To Haves

• Experience writing customer-facing documentation such as knowledge-base articles, runbooks, troubleshooting guides, or installation procedures.
• Experience building automation workflows, including scripted processes, CI/CD pipelines, or AI agent workflows.
• Background in cybersecurity or experience supporting security-focused products.
• Familiarity with docs-as-code workflows, including Markdown, static site generators, and CI/CD for documentation.
• Familiarity with API documentation tools such as Swagger/OpenAPI, Postman, or ReadMe.
• Prior experience developing and delivering technical training.

Responsibilities

• Build and operate AI-driven workflows for documentation production, including draft generation from source code and PRDs, style and terminology enforcement, command verification against live switches, and release-note generation.
• Develop and maintain Claude skills and prompts to enforce consistent document structure and formatting.
• Establish document-control standards for numbering, revision tracking, cross-references, and change management.
• Use Cursor and source-code repositories to extract technical context, verify documented behavior against implementation, and identify undocumented features or changes.
• Own technical documentation across Scaleout, Scaleup, and Orchestration, including installation guides, configuration references, troubleshooting procedures, hardware guides, and API documentation.
• Create content using engineering input, source code, PRDs, and hands-on testing; report bugs when verified product behavior differs from documentation.
• Work with engineering and product teams to document new features, APIs, integrations, and architecture.
• Develop training materials for new product features, support scenarios, and operational procedures.
• Deliver training to the support team through formal release sessions and informal case walkthroughs.
• Turn recurring ticket patterns into documented procedures and training content, and help onboard team members on product knowledge and tools.
• Write security response documents (SIRTs), ensure remediation steps are technically correct and actionable, and standardize incident communication formats and processes.
• Write customer-actionable release notes and ensure releases are documented before shipping.
• Conduct final reviews of customer-facing content, including knowledge-base articles, presentations, UI copy, and email templates; review other teams’ content for clarity, accuracy, and consistency.
• Assist with customer cases during escalations or capacity constraints.
• Support lab work, including test setups, configuration verification, and reproduction of customer-reported issues.
• Contribute to professional services engagements where documentation, training, or technical content is needed.
• Provide additional support across the CX team as needed.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed