Top Tech Jobs & Startup Jobs in Chicago, IL

The role involves designing and building AI-native systems for revenue teams at Upside, including developing applications, partnering with teams, managing the entire stack, and improving system reliability and performance.

The Principal Product Marketing Manager drives customer engagement and retention strategies, creates sales enablement materials, and collaborates with teams to enhance customer value and minimize churn.

The Staff Data Engineer will lead design and implementation of analytics platforms and data products, collaborate cross-functionally, mentor engineers, and drive best practices at Upside.

Lead and hands-on manage the Infrastructure team owning Upside's cloud platform: drive AWS architecture (cell-based), AI-assisted deployment tooling, security, CI/CD, observability, operational excellence, and cross-functional coordination to enable reliable, scalable, and secure platform services.

The Work Design Architect at Upside leads the design of the R&D Operating Blueprint to enhance organizational decision-making and processes, focusing on AI integration to improve systemic efficiency.

Own and modernize Upsides analytics data platform: migrate pipelines, reduce cost, improve governance, design reusable modeling/orchestration patterns, deliver domain-critical data products, lead cross-functional initiatives, mentor engineers, and support ML and product teams.

The Knowledge Systems Architect will design systems for knowledge organization, automate documentation processes, and enhance knowledge artifact legibility to support AI effectiveness in the R&D environment.

Lead a small embedded design and research team to raise polish and consistency across consumer and payments experiences. Build design systems, embed design in discovery with Product/Engineering/Marketing, deepen research practice, apply AI-native scaling, and drive measurable outcomes for onboarding, redemption, and retention.

Lead data analysis projects to help merchant partners understand Upside's impact, manage analytics relationships, and improve product strategy.

Lead data analysis for merchants, manage projects to improve product and acquisition strategies, and communicate insights effectively.