Work Design Architect
The Opportunity
Ai is making individual work faster. However, the harder and more valuable problem is making organizations move faster. This requires understanding how an organization operates, not just in a vague sense, but in a precise, explicit, machine-accessible way. This is known as process legibility.
Opportunity at Upside
We created Upside to transform brick-and-mortar commerce. Our technology uses sophisticated online retail methods like profit measurement, attribution, and incrementality to provide users with more value on their everyday purchases and help brick-and-mortar businesses earn new, profitable customers. Millions of users earn more cashback than any other product, and hundreds of thousands of businesses earn measurable profit. Billions of dollars in commerce run through our platform each year, and the value goes directly back to our retailer partners, the consumers they serve, and important sustainability initiatives.
The Role
The Work Design Architect owns the layer above individual productivity — the operating system that makes organizational decision-making faster, more coherent, and increasingly self-sustaining. This role exists within Upside's R&D organization, which is currently mid-evolution. The R&D Operating Blueprint is being built by the RISE team, and the Work Design Architect leads the effort to design and implement this framework.
Ongoing Responsibilities
Own and steward the R&D Operating Blueprint — keep it current as the organization evolves, run periodic health checks, and make redesign calls when something isn't working.
Lead operating rhythm work: forum design, cadence changes, redesigns, and post-mortems — the ongoing drumbeat of keeping the operating model healthy.
Serve as the internal expert on AI-native process design — the go-to voice for "how do we build this as a system, not a document."
Qualifications
Deep experience in program management, organizational design, or operating model work — you think in systems, not projects.
A genuine point of view on how AI changes organizational dynamics, not just individual workflows — "decisions are now the bottleneck" should land immediately.
Demonstrated ability to design and implement operating models, not just document existing ones.
Experience working across a technical organization without authority — your influence comes from craft and accessibility, not the org chart.
Comfort making complex systems thinking legible to skeptical, busy audiences.
A "first-hire" mindset — you build structure where none exists and don't wait for permission to start.