Knowledge Systems Architect

Meet Upside:

We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retail—profit measurement, attribution, and incrementality—to provide users with more value on their everyday purchases and brick-and-mortar businesses with new, profitable customers. We’ve 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 doesn't fail because companies lack good tools. It fails because the organization isn't 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 can't be relied on.

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

This isn't a writing role. It's a systems design role. The person we're looking for doesn't 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, Confluenc...