Upside jobs

Upside is a fintech/commerce platform company seeking a Principal Data Engineer to architect and evolve their analytics data platform across ~2,000 tables and 100 pipelines. The role involves leading platform modernization, FinOps initiatives, data product design, and mentoring within the analytics engineering function. Located in NYC/Austin/Chicago with remote work, salary $215k–$250k/year, full-time.

Manager, Infrastructure Engineering at Upside, a fintech platform that provides cashback and profit attribution for brick-and-mortar retail. The role leads a core infrastructure team responsible for cloud platform, networking, security, and CI/CD tooling supporting all applications and data products. Responsibilities include AWS environment management, observability and tooling improvements, operational excellence, and incident management. Flexible role spanning Austin, Chicago, DC, NYC with remote option; $185K–$215K salary; requires deep infrastructure/platform engineering experience and people leadership.

The Work Design Architect role sits within Upside's R&D Intelligence, Systems and Enablement (RISE) team and owns designing and stewarding the R&D Operating Blueprint—the organizational operating system that makes decision-making faster and more coherent across the engineering organization. Key responsibilities include leading operating rhythm work (forum design, cadence changes, post-mortems), serving as the internal expert on AI-native process design, and coaching team members implementing the operating model across pod, hive, and org levels. You need deep experience in program management, organizational design, or operating model work; genuine understanding of how AI changes organizational dynamics (not just individual productivity); and a proven track record designing and implementing operating models, not just documenting them. This is a senior IC role (no direct reports) based in Austin, Chicago, DC, or NYC with hybrid flexibility but requiring in-office attendance Monday-Thursday; compensation is $179k-$195k plus equity and benefits. The stand-out detail is the focus on "process legibility"—designing living systems that make right behavior the default—and the explicit need for someone who can work across technical organizations without formal authority, relying on craft and credibility instead.