Top Tech Jobs & Startup Jobs in Chicago, IL

Provide transactional legal support across a multi-brand retail portfolio, including M&A diligence and deal docs, negotiating commercial and real estate contracts, managing litigation, advising on IP/privacy/marketing issues, improving contract lifecycle processes, and partnering cross-functionally to deliver practical legal guidance.

Own and productize an economics and pricing decision system across inventory states, partnering with data science and engineering to produce daily, auditable pricing recommendations that improve margin and capital efficiency. Lead experimentation, governance, and explainability for pricing, markdowns, and liquidation decisions.

The Director of Accounting, AI Operations will manage accounting functions across 13 brands, enhance automation through AI, ensuring a faster financial close. Responsibilities include overseeing reconciliations, improving financial reporting, and optimizing accounting operations.

The Senior Strategy Analyst will support the development of strategic plans, business cases, and decision dashboards by analyzing data and collaborating with leadership on key initiatives.

The Head of People Operations will design and lead an AI-driven HR function, developing systems for workforce planning, performance management, and talent development while fostering a high-performing team.

Lead product execution for retail platforms, integrations, and data foundations. Establish data governance, define integration patterns and data contracts, improve fulfillment/OMS capabilities, evaluate vendors, and enable analytics and AI-driven automation to increase operational efficiency.

The Director of Growth will lead growth strategies, identify conversion constraints, execute commercial initiatives, and establish cross-functional leadership. Emphasis is on data-driven decision-making and building scalable growth playbooks.

Own architecture, development, and reliability of ecommerce web applications (Symfony storefront and Laravel back-office). Lead front-end JavaScript/CSS direction, optimize SQL schemas/queries, improve observability and incident response, reduce legacy technical debt, establish AI-assisted development workflows, mentor engineers, and drive end-to-end delivery of scalable customer-facing features.