Work Design 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 is making individual work faster. That's the easy part. The harder and more valuable problem is making organizations move faster — and that requires something different.

For AI to participate in organizational work — surfacing the right information for a decision, running a process without a human holding it together, flagging when work is stalled at the wrong level — the organization needs to know how it operates. Not in a "we have a Confluence page somewhere" sense. In a precise, explicit, machine-accessible sense: what decisions belong at which level, what rhythm drives work forward, what information should be in which room, and what makes a good decision possible in the first place.

This is process legibility. And most R&D organizations don't have it. Meetings run at the wrong altitude. Decision authority is implicit. Cross-team work relies on a specific person to hold it together — and stalls when that person isn't available. When you add AI agents into that environment, the gaps don't shrink. They become critical.

Upside is building differently. While most organizations are optimizing individual productivity, we're investing in the layer above it — the operating system that makes organizational decision-making faster, more coherent, and increasingly self-sustaining. T...