Top Tech Jobs & Startup Jobs in Chicago, IL

Own the Ascent AI enablement platform roadmap across engineering and enterprise programs. Prioritize shared infrastructure, define specifications, close capability gaps, measure maturity, and connect AI usage to business value. Partner with engineering teams without direct authority, communicate roadmap decisions to technical and nontechnical stakeholders, and stay hands-on with AI coding agents and developer tools.

Own and maintain dbt data models across design, testing, deployment, monitoring, and documentation. Translate ambiguous Marketing and Product needs into reliable data solutions, write design documents, support production issues, create runbooks and schema documentation, and coach junior engineers. The role uses SQL, Python, Snowflake, dbt, Dagster, and AWS while partnering closely with Marketing, Data, and MarTech teams.

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.

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.

Lead consumer growth end-to-end for a hypergrowth app: own conversion, retention, cross-sell, organic growth, and multi-category adoption. Set data-driven strategy, improve product quality and trust, build habit-forming experiences, balance unit economics, and grow a team of PMs while partnering with Design, Data, and Marketing.

Lead strategy and roadmap to build a personalized growth engine using AI and marketing technology. Define requirements across data infrastructure, multi-channel outreach, app surfaces, creative personalization, and incentive systems. Run experimentation, set KPIs, drive cross-vertical adoption, and align engineering, design, data, and marketing to scale repeatable user habits and retention.

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 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 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.