Work Design Architect

Upside; Chicago (IL); Hybrid; USD 198,000 - 215,000; Full time

Benefits offered by this job

Medical, dental, and vision coverage

401(k) program

Unlimited PTO

Lunch reimbursement

Learning and Development stipend

Job summary

Upside is seeking a Work Design Architect to lead the R&D Operating Blueprint and design AI-centric operational systems. This hybrid role requires in-office attendance for parts of the week, encompassing Chicago, Austin, DC, or NYC offices.

The successful candidate will have deep experience in organizational design and program management. Benefits include extensive healthcare coverage, equity, unlimited PTO, and a flexible work environment.

Qualifications

• Deep experience in program management, organizational design, or operating model work.
• Genuine view on AI's impact on organizational dynamics.
• Demonstrated ability to design and implement operating models.

Responsibilities

• Own and steward the R&D Operating Blueprint, keeping it current.
• Lead the operating rhythm work to maintain the health of the operating model.
• Serve as the internal expert on AI-native process design.

Skills

Program management

Organizational design

Complex systems thinking

AI process design

Job description

About Upside

Upside transforms brick‑and‑mortar commerce by applying advanced online‑retail metrics to provide greater value for consumers and retail partners.

Role Overview

As a Work Design Architect you will design and lead the R&D Operating Blueprint, creating an AI‑accessible operating system that speeds organizational decision‑making.

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 necessary.
• Lead operating rhythm work: forum design, cadence changes, redesigns, and post‑mortem analysis to maintain the health of the operating model.
• Serve as the internal expert on AI‑native process design—the go‑to voice for building systems, not documents.

Qualifications

• Deep experience in program management, organizational design, or operating model work—thinking in systems, not projects.
• A genuine point of view on how AI changes organizational dynamics, beyond individual workflows.
• Demonstrated ability to design and implement operating models, not just document existing ones.
• Experience working across a technical organization without formal authority.
• Comfort making complex systems thinking legible to skeptical, busy audiences.
• A first‑hire mindset—building structure where none exists and starting immediately.

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 policy changes.

Compensation

US base salary range US$198,000 – $215,000 + equity + benefits. Final starting pay will be determined based on job‑related skills, experience, qualifications, work location, and market conditions.

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 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 & 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. Everyone is welcome here! If you need accommodations during your application or interview process, please email [e-mail]. This email is for accessibility accommodations only.