Knowledge Systems Architect

Meet Upside:

We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retailprofit measurement attribution and incrementalityto provide users with more value on their everyday purchases and brick-and-mortar businesses with new profitable customers. Weve helped millions of users earn 2 to 3 times more cashback than any other product and hundreds of thousands of brick-and-mortar businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform every year and that value goes directly back to our retailer partners the consumers they serve and important sustainability initiatives.

The Opportunity

AI adoption doesnt fail because companies lack good tools. It fails because the organization isnt legible enough to use them.

For AI to participate in real work drafting documentation surfacing answers flagging anomalies executing workflows it needs material it can actually trust: artifacts that exist are structured are attributed to owners and are fresh enough to act on. Most organizations skip this layer. They deploy AI on top of a knowledge environment full of stale pages shadow Google Docs unattributed decisions and content no one quite believes and then wonder why the outputs cant be relied on.

Upside is building differently. Were investing in the infrastructure layer that makes AI adoption compound rather than stall. The Knowledge Systems Architect owns that layer.

This isnt a writing role. Its a systems design role. The person were looking for doesnt create content they build the conditions under which content creates itself gets maintained automatically and becomes more trustworthy over time. They make the organization legible to machines and to itself.

The scope starts with an R&D focus and expands from there.

Why This Role Exists Now

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 wont 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)

Must have:

• 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

Location:

This hybrid role is based in our Austin Chicago DC or NYC -office attendance is required on Monday Tuesday and Thursday and may increase based on project-based needs and changes to Upsides in-office policy over time.

Compensation:

The US base salary range for this full-time position is $153000 - $165000 equity benefits. The final starting pay will be determined based on job-related skills experience qualifications work location and market conditions. Your recruiter can share more about the specific salary range during the hiring process.

#LI-Hybrid

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Benefits:

• Medical dental and vision coverage starting on Day 1

• Equity (ISOs)

• 401(k) program

• Family planning programs paid parental leave

• Physical fitness and wellness memberships

• Emotional and mental health support programs

• Unlimited PTO 10 paid federal holidays our annual week-long Winter Break

• Flexible work environment

• Lunch reimbursement for in-office employees

• Employee Resource Groups

• Learning and Development stipend

• Transparent culture

• Amazing mission!

Diversity and Inclusion:

Diversity drives innovation and our differences make us stronger. Were passionate about building a workplace that represents a variety of backgrounds skills and perspectives and we do not discriminate based on race religion color national origin gender sexual orientation age marital status veteran status or disability status. Everyone is welcome here!

If theres anything we can do to support a disability or special need during your application or interview process please email

This email is for accessibility accommodations only it should not be used to submit job applications.

Notice To Recruiters And Placement Agencies:

This is an in-house search with a dedicated recruiter. Please do not submit resumes to any person or email address at Upside. Upside is not liable for and will not pay placement fees for candidates submitted by any party or agency other than its approved recruitment partners.

Required Experience:

Staff IC