Top Tech Jobs & Startup Jobs in Chicago, IL

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.

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 product analytics for Upsides consumer app: define KPIs and OKRs, design and analyze A/B tests, perform exploratory and root-cause analyses, forecast revenue impacts, build dashboards and data models, ensure robust instrumentation, and use AI tools to automate and scale experimentation and analytics workflows.

Lead a full-stack Reconciliation team owning transaction-matching pipelines across mobile and backend systems. Drive reliability, observability, and accuracy for post-claim flows, coach and grow engineers, contribute hands-on in high-leverage technical areas, partner cross-functionally, and scale systems and processes to improve transaction success and user trust.

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.

The Senior Director will optimize marketplace operations, manage incident lifecycles, and lead a team to drive growth and data reliability.

Drive application security by running SAST/SCA, threat modeling, vulnerability management, and remediation. Advise on secure architecture, train engineers, support pentests/bug bounties, and administer AWS Control Tower and IAM. Innovate with AI to improve AppSec tooling and practices.

Lead the Consumer Core full-stack team building core functionality across Kotlin Multiplatform front-end and Python/Java back-end. Drive architecture, security, reliability, cost-efficiency, tooling, AI adoption, and cross-functional alignment. Coach engineers, set domain boundaries, represent the team in planning, and scale systems and processes to support Consumer and Partnerships applications.

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.