{"schemaVersion":"jobsearcher.job.v1","id":"46c8a9e8ba298799fc23f592","url":"https://jobsearcher.com/jobs/46c8a9e8ba298799fc23f592","canonicalUrl":"https://jobsearcher.com/jobs/46c8a9e8ba298799fc23f592","title":"Work Design Architect","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.\nThe 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.\nUpside 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.\nRole 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.\nOngoing Responsibilities Own and steward the R&D Operating Blueprint — keep it current, run periodic health checks, and redesign where needed\nLead operating rhythm work: forum design, cadence changes, redesigns, and post-mortems to maintain a healthy operating model\nServe as the internal expert on AI-native process design — the go-to voice for building systems, not documents\nWhat You Should Have Deep experience in program management, organizational design, or operating model work; you think in systems, not projects\nA clear point of view on how AI changes organizational dynamics — decisions are the bottleneck\nDemonstrated ability to design and implement operating models, not just document them\nExperience working across a technical organization without direct authority; influence comes from craft and accessibility\nAbility to make complex systems thinking legible to busy audiences\nA \"first-hire\" mindset — you build structure where none exists and don’t wait for permission to start\nLocation 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.\nCompensation 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.\nBenefits Medical, dental, and vision coverage starting on Day 1\nEquity (ISOs)\n401(k) program\nFamily planning programs + paid parental leave\nPhysical fitness and wellness memberships\nEmotional and mental health support programs\nUnlimited PTO + 10 paid federal holidays + annual Winter Break\nFlexible work environment\nLunch reimbursement for in-office employees\nEmployee Resource Groups\nLearning and Development stipend\nTransparent culture\nDiversity 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 accommodations@upside.com. This email is for accessibility accommodations only, not for submitting job applications.\n\n#J-18808-Ljbffr","company":"Upside Services","rawCompany":"upside services","city":"Springfield","state":"IL","isRemote":false,"isActive":true,"createdAt":"2026-06-20T03:23:46.001Z","occupations":[{"code":"27-1029.00","title":"Designers, All Other","slug":"designers-all-other"},{"code":"15-1255.00","title":"Web and Digital Interface Designers","slug":"web-and-digital-interface-designers"},{"code":"15-1299.08","title":"Computer Systems Engineers/Architects","slug":"computer-systems-engineers-architects"}],"industries":[{"code":"541512","title":"Computer Systems Design Services","slug":"computer-systems-design-services"},{"code":"513210","title":"Software Publishers","slug":"software-publishers"},{"code":"541511","title":"Custom Computer Programming Services","slug":"custom-computer-programming-services"}],"jobPosting":{"@context":"https://schema.org","@type":"JobPosting","title":"Work Design Architect","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.\nThe 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.\nUpside 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.\nRole 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.\nOngoing Responsibilities Own and steward the R&D Operating Blueprint — keep it current, run periodic health checks, and redesign where needed\nLead operating rhythm work: forum design, cadence changes, redesigns, and post-mortems to maintain a healthy operating model\nServe as the internal expert on AI-native process design — the go-to voice for building systems, not documents\nWhat You Should Have Deep experience in program management, organizational design, or operating model work; you think in systems, not projects\nA clear point of view on how AI changes organizational dynamics — decisions are the bottleneck\nDemonstrated ability to design and implement operating models, not just document them\nExperience working across a technical organization without direct authority; influence comes from craft and accessibility\nAbility to make complex systems thinking legible to busy audiences\nA \"first-hire\" mindset — you build structure where none exists and don’t wait for permission to start\nLocation 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.\nCompensation 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.\nBenefits Medical, dental, and vision coverage starting on Day 1\nEquity (ISOs)\n401(k) program\nFamily planning programs + paid parental leave\nPhysical fitness and wellness memberships\nEmotional and mental health support programs\nUnlimited PTO + 10 paid federal holidays + annual Winter Break\nFlexible work environment\nLunch reimbursement for in-office employees\nEmployee Resource Groups\nLearning and Development stipend\nTransparent culture\nDiversity 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 accommodations@upside.com. This email is for accessibility accommodations only, not for submitting job applications.\n\n#J-18808-Ljbffr","datePosted":"2026-06-20T03:23:46.001Z","dateModified":"2026-06-20T03:23:46.001Z","hiringOrganization":{"@type":"Organization","name":"Upside Services","sameAs":"https://jobsearcher.com"},"jobLocation":{"@type":"Place","address":{"@type":"PostalAddress","addressLocality":"Springfield","addressRegion":"IL","addressCountry":"US"}},"identifier":{"@type":"PropertyValue","name":"JobSearcher","value":"46c8a9e8ba298799fc23f592"},"url":"https://jobsearcher.com/jobs/46c8a9e8ba298799fc23f592"}}