> Markdown version of [/jobs/ext/2027746-knowledge-systems-architect](https://www.wearedevelopers.com/jobs/ext/2027746-knowledge-systems-architect). Every page supports `.md` or `Accept: text/markdown`. Links point to the HTML versions so they work for humans too. Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Knowledge Systems Architect - **Company:** The Upside - **Location:** Chicago, IL, United States - **Salary:** $153,000.0 - $165,000.0 - **Contract:** Permanent contract - **Skills:** Artificial Intelligence, Confluence, Software Documentation, Knowledge Management, Knowledge-Based Systems, Routing, Large Language Models, Tools for Reporting, Virtual Agents, Looker Analytics, Human in the Loop - **Published:** August 11, 2026 - **Apply:** https://www.careerbuilder.com/job-details/knowledge-systems-architect-chicago-il--c428bb52-9111-4b94-9d93-acf059417947 ## About the Role * Deep experience in knowledge management, information architecture, or technical writing with a strong systems orientation you think in infrastructure, not documents * Demonstrated ability to design and implement governance frameworks, not just follow them * Hands-on experience with Confluence and/or Glean (or equivalent enterprise knowledge and search platforms) * Comfort working across data, analytics, and tooling to instrument and measure knowledge health * A "first-hire" mindset you thrive as a strategist, operator, and change agent. This is not a large team with an existing playbook. * Strong written communication; you may not write the content but youll define what good looks like * Experience with AI-assisted documentation workflows or LLM-based content tooling Strong plus: * Background working in a technical environment (R&D, Engineering, or Product-adjacent) * Familiarity with analytics tools (Hex, Looker, or similar) for building dashboards * Experience in an enablement or internal developer-relations type role ## Description Upside has strong documentation instincts in some teams and gaps in others. We have powerful tools Glean, Confluence, AI documentation agents but adoption is uneven and the workflows that would make them self-sustaining dont exist yet. Documentation still depends too much on heroic individual efforts. The Knowledge Systems Architect changes that. Instead of being the person who writes the thing or answers the Slack message, theyre the person who designs the system so neither of those is necessary. You won't be starting from scratch but from a partially-built foundation: some islands of good practice, some legacy sprawl, and AI capabilities that are ahead of our governance. A significant part of the job is turning that foundation into a coherent, durable system. This is a high-leverage, high-visibility role inside the R&D Intelligence, Systems and Enablement (RISE) team. Youll work directly with the VP of RISE and alongside Engineering, Product, and IO to make Upsides knowledge infrastructure a genuine competitive advantage. Key Initiatives 1. Build the Artifact Legibility Foundation for R&D The hardest part of AI enablement isnt deploying agents its ensuring the knowledge artifacts those agents rely on are actually trustworthy. That means documents that are structured, attributed, current, and verifiable: not pages nobody has touched in two years, decisions buried in Slack threads, or content people cite without quite believing. Youll map the current state of artifact legibility across R&D, identify the highest-leverage gaps, and design the interventions governance frameworks, lifecycle rules, ownership models, structural standards, AI agents that close them. This is the core of the role. 2. Automate the Documentation Lifecycle Documentation shouldnt require someone to remember to do it. The goal is a world where documentation happens as a natural output of how work gets done triggered by product releases, embedded in team workflows, quality-checked automatically. Youll own the design and rollout of AI-assisted documentation pipelines: integrating agents into the Product Development Lifecycle and release workflows, setting up automated review triggers, defining when human oversight is mandatory and when it isnt. We have early infrastructure here (Glean agents, a product documentation agent, etc.). Your job is to operationalize it and make it irreversible. 3. Solve the Routing Problem Today, requests for documentation help, knowledge infrastructure, and tool guidance flow to a person. That doesnt scale and it creates a single point of failure. Youll replace that with a system: a well-governed intake pathway, enabled by an AI agent, and self-serve guidance that handles the majority of inbound without a human in the loop. The goal isnt efficiency its changing the mental model from "ask an expert" to "I do this well on my own." 4. Build Knowledge Observability You cant govern what you cant see. We need real-time visibility into the health of our knowledge environment: whats stale, whats trusted, whats being used, whats not, and which teams are owning their content versus letting it drift. Youll define the metrics framework (Extending the KEI framework or replacing it altogether), instrument the measurement infrastructure using Confluence and Glean analytics, and create dashboards that make content health visible to the teams that own it, and highlight the system improvements thatll advance artifact legibility forward. 5. Drive the Shift from Service Model to Enablement Model The service-oriented model: teams request, the knowledge team delivers doesnt compound. Youll continue the push towards an enablement-orient model: teams owning their own documentation with the right templates, agents, structure, and governance to do it well without needing a specialist. Youll design and run that enablement program alongside the rest of the RISE team: self-serve tooling, space governance for Confluence, team-level KPI views, and the cultural change management that makes ownership stick. Ongoing Responsibilities: * Own Confluence and Glean as the primary business administrator for both platforms; maintain governance models and usage standards * Maintain documentation standards, style guidance, and structural templates (as system assets, not as a writer) * Define and manage lifecycle rules: what gets refreshed, archived, and retired - and when * Run content health audits on a defined cadence and surface insights to leadership and team owners * Serve as the internal expert on when and how AI can be safely used in documentation workflows - and maintain those guardrails as AI tooling evolves * Manage knowledge infrastructure transitions (new team spaces, ownership migrations, tool changes), This hybrid role is based in our Austin, Chicago, DC, or NYC office. In-office attendance is required on Monday, Tuesday, and Thursday and may increase based on project-based needs and changes to Upside's in-office policy over time. ## Related Videos - [New AI-Centric SDLC: Rethinking Software Development with Knowledge Graphs](https://www.wearedevelopers.com/videos/1417-new-ai-centric-sdlc-rethinking-software-development-with-knowledge-graphs) - [Creating a routing app with Google Maps API from scratch](https://www.wearedevelopers.com/videos/831-creating-a-routing-app-with-google-maps-api-from-scratch) - [42 x 2 Canvases Later: Two Years, Two Minds, Many Lessons](https://www.wearedevelopers.com/videos/1458-42-x-2-canvases-later-two-years-two-minds-many-lessons) - [Guiding Agentic AI with Vue](https://www.wearedevelopers.com/videos/2033-guiding-agentic-ai-with-vue) - [Designing UX for SRE Agents in High-Stakes Incidents](https://www.wearedevelopers.com/videos/100003-designing-ux-for-sre-agents-in-high-stakes-incidents) - [A Technical Introduction to Bitcoin's 2nd Layer- The Lightning Network](https://www.wearedevelopers.com/videos/15-a-technical-introduction-to-bitcoin-s-2nd-layer-the-lightning-network) ## Related Articles - [Graph and AI Trends 2026: Why Is AI Running but Not Yet Delivering?](https://www.wearedevelopers.com/magazine/680-graph-and-ai-trends-2026-why-is-ai-running-but-not-yet-delivering) - [Never delegate the understanding](https://www.wearedevelopers.com/magazine/749-never-delegate-the-understanding) - [Navigating the AI Shift](https://www.wearedevelopers.com/magazine/629-navigating-the-ai-shift) - [Coffee with Developers - Maria Apazoglou - Making AI understandable for all in production](https://www.wearedevelopers.com/magazine/475-coffee-with-developers-maria-apazoglou-making-ai-understandable-for-all-in-production) - [13 AI Tools You Have to Try](https://www.wearedevelopers.com/magazine/219-13-ai-tools-you-have-to-try) - [Everything a Developer Needs to Know About MCP with Neo4j](https://www.wearedevelopers.com/magazine/604-everything-a-developer-needs-to-know-about-mcp-with-neo4j)