Work Design Architect

Upside; Illinois; Hybrid; USD 198,000 - 215,000; Full time

Benefits offered by this job

Medical, dental, and vision coverage

Equity (ISOs)

401(k) program

Unlimited PTO

Flexible work environment

Learning and Development stipend

Job summary

Upside is seeking a Work Design Architect to help build an operating system for faster organizational decision-making. This senior role involves owning the R&D Operating Blueprint, leading operating rhythm work, and serving as an expert in AI-native process design.

Successful candidates will have deep program management experience, the ability to work across technical teams, and a systems-thinking mindset. The role is hybrid with a base salary range of $198,000 - $215,000, plus equity and benefits.

Qualifications

• Deep experience in program management or organizational design.
• Ability to make complex systems legible to busy audiences.
• Experience working across a technical organization without direct authority.

Responsibilities

• Own and steward the R&D Operating Blueprint.
• Lead operating rhythm work and maintain a healthy operating model.
• Serve as the internal expert on AI-native process design.

Skills

Program management

Organizational design

AI-native process design

Influencing without authority

Systems thinking

Job description

Overview

Upside transforms brick-and-mortar commerce. Our technology brings online-retail sophistication—profit measurement, attribution, and incrementality—to provide value on everyday purchases and help brick-and-mortar businesses gain new, profitable customers. We’ve helped millions earn brighter cashback and support retailer partners, consumers, and sustainability initiatives.

The Opportunity

AI is making individual work faster. The harder and more valuable problem is enabling organizations to move faster. For AI to participate in organizational work, the organization must have precise, machine-accessible definitions of decisions, rhythms, information, and what makes a good decision possible.

Upside is building the operating system that makes organizational decision-making faster, more coherent, and self-sustaining. The Work Design Architect owns that layer, designing a living system — explicit, AI-accessible, and self-correcting — that makes the right behavior the easy default.

Role and Scope

This is a senior IC lead role within R&D. There are no direct reports. Influence comes from craft and credibility as the primary means to drive the operating model.

Ongoing Responsibilities

• Own and steward the R&D Operating Blueprint — keep it current, run periodic health checks, and redesign where needed
• Lead operating rhythm work: forum design, cadence changes, redesigns, and post-mortems to maintain a healthy operating model
• Serve as the internal expert on AI-native process design — the go-to voice for building systems, not documents

What You Should Have

• Deep experience in program management, organizational design, or operating model work; you think in systems, not projects
• A clear point of view on how AI changes organizational dynamics — decisions are the bottleneck
• Demonstrated ability to design and implement operating models, not just document them
• Experience working across a technical organization without direct authority; influence comes from craft and accessibility
• Ability to make complex systems thinking legible to 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 Austin, Chicago, DC, or NYC. In-office attendance is required on Monday, Tuesday, and Thursday; may increase based on project needs and policy changes.

Compensation

The US base salary range for this full-time position is $198,000 - $215,000 + equity + benefits. Final starting pay depends on skills, experience, location, and market conditions. Your recruiter can share more during the hiring process.

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 + annual Winter Break
• Flexible work environment
• Lunch reimbursement for in-office employees
• Employee Resource Groups
• Learning and Development stipend
• Transparent culture

Diversity And Inclusion

Diversity drives innovation. Upside is committed to a workplace representing varied backgrounds, skills, and perspectives. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status. Everyone is welcome here. If accommodations are needed during the application or interview process, please email [e-mail]. This email is for accessibility accommodations only, not for submitting job applications.