Upside is a nationally scalable housing stability platform that partners with health plans and employers to identify and stabilize people experiencing housing instability.
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. The Work Design Architect owns that layer. The Work Design Architect builds the operating system that fixes this. Not by writing playbooks that people are supposed to follow. By designing a living system — explicit, AI-accessible, and self-correcting — that makes the right behavior the easy default. The scope is R&D. The model, if it works, travels. Why This Role Exists Now Upside's R&D organization is mid-evolution. There are forums, rhythms, and coordination structures in place — but they're running at inconsistent altitudes, with implicit decision authority and uneven data inputs. Good work depends too much on specific people holding context. The organization can move fast on individual tasks. It can't yet steer faster as a whole. The R&D Intelligence, Systems and Enablement (RISE) team is building the R&D Operating Blueprint — a framework that designs and instruments how R&D operates at every level: from pod to hive to org. The architecture is outlined. The design table is mostly empty cells. And the enablement layer — the thing that makes the operating model actually run without RISE in the room — doesn't yet exist. The Work Design Architect leads that effort. They provide the architectural coherence across all three levels, coach the team members doing the implementation work, and keep the vision connected to what's actually happening on the ground. This is a senior IC lead role. No direct reports, no career management. The influence comes from craft and credibility — which is exactly how the best operating model work gets done. 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" What you should have: - 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 Location: 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. Compensation: The US base salary range for this full-time position is $198,000 - $215,000 + 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 #LI-NE1 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 drive