Top Tech Jobs & Startup Jobs in Chicago, IL

Develop statistical models, experiments, causal inference methods, and scalable analytical workflows to generate business insights. Partner cross-functionally with Client Experience, Strategy, Marketing, Styling, Support, and Engineering teams to define metrics and improve products. Own analytical initiatives from framing through delivery, communicate executive-ready recommendations, mentor data scientists, and leverage LLMs and AI agents to accelerate analysis and workflows.

Own end-to-end delivery of platform initiatives, designing scalable infrastructure, APIs, gateways, backend services, self-service tooling, and automation. Evaluate and implement AI agents and workflows within developer tooling, improve reliability and engineering productivity, lead technical design reviews, mentor engineers, and influence cross-functional stakeholders. The role requires operating complex production systems across Ruby/Rails, Python, Rust, React/TypeScript, GraphQL, and cloud infrastructure.

Manages creative projects and external creator content production across paid and organic social channels. Develops briefs, coordinates timelines and approvals, supports social content planning, tracks cultural trends, and connects creative performance insights to future content development. Improves creative workflows and uses AI tools to enhance ideation, reporting, content planning, and production efficiency.

Manage Stitch Fix’s integrated marketing calendar and coordinate cross-functional campaigns across merchandising, CRM, social, PR, growth, styling, creative, site, app, and blog channels. Own blog strategy from planning through publishing, identify culturally relevant marketing opportunities, support creative refreshes and brand partnerships, and coordinate vendors. Use AI-powered tools and collaboration platforms to improve research, content development, project planning, and workflow efficiency.

Lead technical direction and delivery for order management systems supporting checkout, order lifecycles, fulfillment orchestration, and partner integrations. Design reliable distributed services and workflows, make architectural tradeoffs, and improve scalability, correctness, observability, testing, and operational readiness. Partner cross-functionally to define scope and outcomes, lead incidents and remediation, manage launches, and mentor engineers. Work across Go, Ruby on Rails, PostgreSQL, AWS, Kafka, Temporal, Datadog, and AI-assisted development tools.

Leads a team of machine learning engineers and data scientists developing and deploying styling algorithms and personalized client experiences. Owns AI and ML strategy, product roadmap contributions, experimentation, production deployment, code quality, and data practices. Partners with product, design, merchandising, styling, and business teams to optimize personalization outcomes while coaching the team and fostering collaboration, innovation, and technical excellence.

Leads corporate strategy planning, OKRs, monthly business reviews, go-to-market strategies, and high-priority initiatives from planning through execution. Partners with senior leaders across functions to translate data and insights into recommendations, align teams, establish accountability, and deliver measurable outcomes. Develops scalable strategic tools and processes while using AI-enabled technologies to improve research, decision-making, and execution.

Leads Stitch Fix’s Product Algorithms portfolio across Growth, Styling, and Fix & Freestyle. Defines strategy and roadmaps for machine learning, AI, experimentation, personalization, and product analytics; drives scalable production capabilities and measurable business outcomes; improves planning, operational readiness, incident management, and decision-making; and builds a high-performing organization of managers and senior technical contributors while partnering with executive and cross-functional stakeholders.

Build and improve Stitch Fix's cloud-native platform and developer tooling. Develop IaC, CI/CD, containerized workflows, and automation to improve deployment reliability and developer experience. Collaborate with engineers, debug systems, and explore LLM-powered tooling under mentorship.

Lead cross-channel CRM lifecycle programs (Email, Push, SMS, packaging inserts) to reduce churn and drive retention. Partner with Creative, Data Science, Product, and Engineering to design personalized, data-driven campaigns, optimize workflows with ESPs and AI tools, and report performance and strategic insights to leadership.