Job Overview
Location
Austin
Job Type
Full-time
Category
Management
Date Posted
May 28, 2026
Full Job Description
đź“‹ Description
- • The Work Design Architect owns the R&D Operating Blueprint, designing a living, AI-accessible system that makes organizational decision-making faster, more coherent, and self-sustaining by fixing process legibility gaps in R&D.
- • Day to day, the role involves stewarding the R&D Operating Blueprint, leading operating rhythm work (forum design, cadence changes, post-mortems), and serving as the internal expert on AI-native process design to ensure the operating model runs without dependency on specific individuals.
- • Upside Services, Inc. transforms brick-and-mortar commerce by using online retail sophistication to increase cashback for users and profit for businesses, with billions in commerce flowing through its platform annually, and is now investing in the organizational layer above individual productivity to enable AI to participate in work effectively.
- • The person will achieve architectural coherence across pod, hive, and org levels of R&D, coach implementation team members, and enable the organization to steer faster as a whole by making the right behavior the easy default through explicit, self-correcting systems.
🎯 Requirements
- • 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 don't wait for permission to start
🏖️ Benefits
- • Medical, dental, and vision coverage starting on Day 1
- • Equity (ISOs)
- • Unlimited PTO + 10 paid federal holidays + our annual, week-long Winter Break
- • Physical fitness and wellness memberships
- • Emotional and mental health support programs
- • Learning and Development stipend
Skills & Technologies
About Upside Services, Inc.
Upside Services provides a cash-back platform that connects consumers with nearby fuel stations, grocery stores, and restaurants. The company earns revenue through performance-based marketing agreements with merchants, who pay only when Upside drives incremental profit above baseline sales. The mobile app delivers personalized offers and processes rebates to users’ bank accounts or digital wallets. Founded in Washington, D.C., Upside uses anonymized transaction data and machine-learning models to forecast demand and set dynamic incentives, aiming to increase foot traffic and basket size for partner businesses while rewarding consumer loyalty.
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