Work Design Architect

Meet Upside:

We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retailprofit measurement attribution and incrementalityto provide users with more value on their everyday purchases and brick-and-mortar businesses with new profitable customers. Weve 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. Thats 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 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 dont 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 isnt available. When you add AI agents into that environment the gaps dont shrink. They become critical.

Upside is building differently. While most organizations are optimizing individual productivity were 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

Upsides R&D organization is mid-evolution. There are forums rhythms and coordination structures in place but theyre 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 cant 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 doesnt 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 whats 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 isnt 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 dont wait for permission to start

Location:

This hybrid role is based in our Austin Chicago DC or NYC -office attendance is required on Monday Tuesday and Thursday and may increase based on project-based needs and changes to Upsides in-office policy over time.

Compensation:

The US base salary range for this full-time position is $198000 - $215000 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 drives innovation and our differences make us stronger. Were 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. Everyone is welcome here!

If theres anything we can do to support a disability or special need during your application or interview process please email

This email is for accessibility accommodations only it should not be used to submit job applications.

Notice To Recruiters And Placement Agencies:

This is an in-house search with a dedicated recruiter. Please do not submit resumes to any person or email address at Upside. Upside is not liable for and will not pay placement fees for candidates submitted by any party or agency other than its approved recruitment partners.

Required Experience:

Staff IC