Top Tech Jobs & Startup Jobs in Chicago, IL

Own the strategy, roadmap, and growth of Upside’s restaurant vertical. Adapt incrementality measurement and offer optimization to restaurant economics, build merchant-facing reporting and onboarding products, and drive partner adoption, retention, and profitability. Partner with engineering, data science, design, sales, account management, and marketing while making integration decisions across POS, payments, and data systems. Establish OKRs and lead a 0-to-1 business area without direct authority.

Leads the Merchant & Pay engineering organization, overseeing managers and teams responsible for merchant, partner, payment, and internal tooling systems. Owns technical strategy, multi-year roadmaps, reliability, scalability, security, engineering standards, and generative AI adoption. Partners with Product, Data, Security, and company leadership while recruiting, developing, and retaining engineering talent. Requires extensive engineering leadership experience, AWS expertise, marketplace or payments experience, and experience scaling business-critical platforms.

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.

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.

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.

Manage enterprise restaurant accounts from onboarding through long-term growth. Improve retention, educate clients using customized data-driven materials, identify expansion opportunities, mitigate churn risk, lead monthly business reviews, interpret account data, and collaborate with analytics, product, marketing, and operations teams to strengthen retailer relationships.

Manage strategic enterprise accounts in the fuel and convenience-store industries, guiding onboarding, retention, growth, and expansion. Build account plans, conduct performance reviews, interpret data, create reports and case studies, monitor account health, address churn risks, and identify expansion opportunities. Partner with analytics, product, marketing, and operations teams while maintaining relationships with senior client stakeholders. The role includes up to 20% travel.