Job Description Insight Global is seeking a highly organized, operationally minded Technical Documentation & Diagramming Specialist to support a Security team. This person will be responsible for translating complex technical systems, scripts, workflows, and infrastructure designs into clear documentation and architectural diagrams. The ideal candidate thinks like an engineer, enjoys solving puzzles, and can visually articulate how technologies connect, even if they don’t have deep security experience. We can pay anywhere from $45-65/hour depending on experience. Responsibilities for Documentation & Diagramming: - Create and maintain detailed architectural diagrams using Lucidchart (SSO, paid version). - Produce diagrams in alternative tools such as Draw.io or other free platforms if needed. - Document end‑to‑end technology workflows, system behaviors, and platform interactions. - Convert technical explanations into visuals (including simple, “cartoon‑style” references when helpful). - Capture how scripts, automations, and integrations work at a functional - not code‑level - depth. - Maintain all documentation in Confluence and ensure links, references, and versioning are accurate. Cloudflare & Infrastructure Mapping - Review existing Cloudflare configurations and compare them against Zero Trust Network Access (ZTNA) desired -future state. - Diagram Cloudflare-to-CFA (infrastructure) mappings and assist in documenting ZTNA onboarding processes. - Support projects involving JAMF and Tanium MDM posture checks flowing into Cloudflare for additional validations. Workflow & Automation Documentation - Map how JIRA automations trigger webhooks, funnel into Windmill, execute scripts, and return outputs back to JIRA. - Document the “next level up” of each workflow—how systems connect, the purpose of each component, and how data flows. - Ensure every diagram includes system connections, integration points, and a link back to related Confluence pages. General Responsibilities - Participate in platform onboarding to gain access to Cloudflare, ZTNA tools, and other relevant systems. - Translate engineers’ explanations into structured diagrams without requiring repeated clarification. - Utilize AI tools (e.g., ChatGPT) to speed up interpretation of scripts - while still demonstrating base understanding. - Support multiple ongoing projects by documenting current state and desired end state. We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to HR@insightglobal.com.To learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy: https://insightglobal.com/workforce-privacy-policy/. Skills and Requirements - Experience producing technical documentation and system diagrams. - Familiarity with Lucidchart, Draw.io, or similar diagramming tools. - Operational/technical background with the ability to think like an engineer. - Understanding of general IT architecture, system integrations, APIs, webhooks, and automation flows. - Strong communication skills and ability to translate complex concepts simply. - Curiosity-driven mindset; comfortable using AI to interpret scripts and workflows. - Must be a strong personality and cultural fit with the Security Architecture team. Must live in states listed below: - Connecticut - Delaware - District of Columbia - Florida - Georgia - Illinois - Iowa - Maryland - Massachusetts - New Jersey - New York - North Carolina - Ohio - Oregon - Pennsylvania - Texas - Utah - Virginia - Exposure to Cloudflare, ZTNA, JAMF, Tanium, JIRA, Confluence, or automation platforms (e.g., Windmill). - Understanding of device posture management concepts. - Prior work supporting a security architecture or IT engineering team.