Work Design Architect at Upside


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Upside is Hiring

Job Info:
  • Company Upside
  • Position Work Design Architect
  • Location Chicago
  • Source Empllo
  • Published May 27, 2026
  • Category Design
  • Type Full-Time
  • Salary $179k - $195k


Job Description

πŸ“‹ Description

  • Own and steward the R&D Operating Blueprint; keep it current.
  • Lead operating rhythm work: forum design, cadence changes, post-mortems.
  • Serve as internal expert on AI-native process design.

🎯 Requirements

  • Deep experience in program management, organizational design, or operating model work β€” you think in systems, not projects
  • A genuine point of view on how AI changes organizational dynamics, not just individual workflows β€” "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 β€” 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 β€” you build structure where none exists and don't wait for permission to start

🎁 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