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 precisely, explicitly, and in a machine-accessible way. Most R&D organizations lack this understanding, leading to inefficiencies and challenges.
Opportunity at Upside
We created Upside to transform brick-and-mortar commerce using sophisticated online retail techniques. Our platform helps millions of users earn more cashback and provides brick-and-mortar businesses with new, profitable customers. Billions of dollars in commerce flow through our platform annually, benefiting retailers, consumers, and 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 self-sustaining. This role exists within Upside's R&D organization, which is currently mid-evolution. The R&D Operating Blueprint is being built to design and instrument how R&D operates at various levels, from pods to hives to orgs. The Work Design Architect leads this effort, providing architectural coherence, coaching implementation teams, and connecting the vision to reality on the ground.
Ongoing Responsibilities
Own and steward the R&D Operating Blueprint, ensuring it remains current as the organization evolves, conducting periodic health checks, and making redesign calls when necessary.
Lead operating rhythm work, including forum design, cadence changes, redesigns, and post-mortems, to keep the operating model healthy.
Act as the internal expert on AI-native process design, guiding the team on how to build systems rather than just documents.
Qualifications
Deep experience in program management, organizational design, or operating model work, with a focus on systems thinking.
A genuine point of view on how AI impacts organizational dynamics, beyond just individual workflows.
Demonstrated ability to design and implement operating models, not just document existing ones.
Experience working across a technical organization without formal authority, influencing through craft and accessibility.
A "first-hire" mindset, building structure where none exists and taking initiative.
Location and Benefits
This hybrid role is based in one of Upside's offices: Austin, Chicago, DC, or NYC. In-office attendance is required on Monday, Tuesday, and Thursday, with potential increases based on project needs and changes to Upside's in-office policy. The compensation range is $198,000 - $215,000, including equity and benefits. Additional perks include medical, dental, and vision coverage, a 401(k) program, family planning programs, paid parental leave, physical fitness and wellness memberships, emotional and mental health support programs, unlimited PTO, and an annual Winter Break. Employee Resource Groups and learning and development stipends are also provided.