Top Tech Jobs & Startup Jobs in Chicago, IL

Lead the architecture and evolution of DraftKings’ machine learning platform, including real-time data pipelines, lakehouse governance, distributed data systems, and scalable model-serving infrastructure. Establish engineering standards, guide complex initiatives, improve reliability and cloud cost efficiency, and partner across engineering and data teams. The role also includes mentoring engineers, managing production operations, and developing AI-assisted automation tools.

Build, fine-tune, evaluate, and deploy computer vision and multimodal machine learning models in production. Develop scalable data pipelines, evaluation frameworks, real-time processing systems, and cloud infrastructure with monitoring and automated scaling. Improve image processing, barcode decoding, and OCR capabilities while partnering with engineering and fulfillment teams. Contribute through code reviews, documentation, testing, technical leadership, and mentorship.

Build and moderate DraftKings’ Discord community by engaging sports betting fans, creating real-time content and events, responding to questions, monitoring sentiment, and sharing community insights cross-functionally. Support live-event coverage during evenings, weekends, and major sporting moments while maintaining a welcoming, responsible, and trusted community environment.

Handles general litigation and legal risk, including assessing lawsuits and complaints, drafting court filings, supporting disputes, resolving legal threats, representing the company in small claims court, and responding to regulatory inquiries. Provides practical legal guidance to internal teams, collaborates with outside counsel, and supports investigations and litigation strategy.

Leads knowledge management strategy and a team of knowledge writers, overseeing content quality, information architecture, governance, and lifecycle management. Partners cross-functionally to translate complex processes into accessible content for customers and employees. Drives projects, analytics-based improvements, and AI-powered search and automation initiatives to improve knowledge discovery, operational efficiency, and customer experience.

Develop and architect scalable iOS applications used by millions of customers. Lead mobile engineering practices involving clean architecture, dependency injection, performance optimization, testing, reliability monitoring, and maintainable code. Collaborate with Product, Design, and Engineering teams to deliver features, stay current with iOS technologies, and promote technical excellence across the iOS engineering community.

Manage prediction-market operations, including market creation, configuration, launches, settlements, member support, real-time surveillance, KPI reporting, and issue escalation. Collaborate with engineering, regulatory, analytics, product, clearinghouse, and ecosystem partners to maintain compliant, liquid, and smoothly functioning markets. The role requires shift flexibility for surveillance coverage and may require obtaining a state gaming license.

Build and maintain scalable platform tools, infrastructure, and automation supporting software development and deployment. Develop C#/.NET solutions, manage Kubernetes environments, implement Helm and GitOps practices, and improve distributed-system reliability, observability, performance, and deployment strategies. Troubleshoot complex infrastructure issues, collaborate with engineering stakeholders, conduct code reviews, and mentor engineers. The role requires cloud-platform experience and expertise in microservices, containerization, and modern application delivery.

Configure and test loyalty bonus offers, verify eligibility and messaging, troubleshoot issues, monitor live promotions, and collaborate with CRM, Marketing, Customer Experience, and other teams. The role also supports process improvements, automation, AI adoption, and operational efficiency while ensuring accurate and reliable rewards experiences.

Corporate Counsel, General Litigation will assess and manage litigation risks, develop dispute strategies, draft and review court filings, negotiate with opposing counsel, and coordinate with outside counsel. The role also represents the company in small claims matters, responds to regulatory and Attorney General inquiries, and provides practical legal guidance to internal teams. Candidates need at least five years of relevant litigation experience, a JD from an ABA-accredited law school, and Massachusetts Bar membership or eligibility.