Architect- Architecture Design

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.

Upside is building differently. 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. The model, if it works, travels.

There are forums, rhythms, and coordination structures in place — but they're running at inconsistent altitudes, with implicit decision authority and uneven data inputs. 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. 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.

No direct reports, no career management. The influence comes from craft and credibility — which is exactly how the best operating model work gets done.

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"

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

A "first‑hire" mindset — you build structure where none exists and don't wait for permission to start

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.

The US base salary range for this full‑time position is $179,000 - $195,000 + equity + benefits. Medical, dental, and vision coverage starting on Day 1

Equity (ISOs)

Unlimited PTO + 10 paid federal holidays + our annual, week‑long Winter Break

Flexible work environment

Lunch reimbursement for in‑office employees

Diversity and Inclusion
Diversity drives innovation, and our differences make us stronger. We’re passionate about building a workplace that represents a variety of backgrounds, skills, and perspectives, and we do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. If there's anything we can do to support a disability or special need during your application or interview process, please email View email address on click.appcast.io email is for accessibility accommodations only, it should not be used to submit job applications.

This is an in‑house search with a dedicated recruiter.