Top Tech Jobs & Startup Jobs in Chicago, IL

Leads knowledge management strategy and a team of knowledge writers. Oversees content standards, information architecture, governance, quality, lifecycle management, analytics, and cross-channel knowledge experiences for customers and employees. Partners cross-functionally to translate complex processes into accessible content, manages projects, and advances AI-powered search, automation, and scalable content practices.

Manage prediction-market operations, including market creation, configuration, launches, settlement, member support, surveillance, KPI reporting, and liquidity coordination. Monitor activity for anomalies and escalate potential trade-practice violations. Collaborate with engineering, regulatory, analytics, product, clearinghouse, and ecosystem partners to support compliant, reliable market operations and new feature launches. Shift coverage may be required for real-time surveillance.

Develop and architect scalable iOS applications serving millions of users. Collaborate with Product, Design, and Engineering to deliver features, promote clean architecture and iOS best practices, monitor performance and crash analytics, and guide technical excellence. Requires strong Swift, SwiftUI, MVVM, API integration, persistence, testing, and code quality expertise.

Leads the Workday platform and service delivery function, managing consulting partners, budgets, capacity, priorities, technical requirements, configurations, and issue resolution across HCM, Recruiting, Payroll, Time and Attendance, and Scheduler. Partners with People teams and stakeholders, leads Workday training and access programs, tracks performance metrics, and supports compliance, audit evidence, and Sarbanes-Oxley controls.

Manage general litigation and legal risk across the business. Responsibilities include assessing lawsuits and legal threats, developing response strategies, drafting and reviewing court filings, guiding outside counsel, negotiating dispute resolutions, representing the company in small claims court, responding to regulatory inquiries, and advising internal stakeholders on emerging legal issues.

Design and evolve the architecture of DraftKings’ regulated prediction-markets exchange. Own the technical roadmap, distributed-system foundations, scalability, reliability, performance, operational health, and resilience testing. Collaborate with product, infrastructure, platform, brokers, market makers, and clearing partners. Contribute hands-on to critical systems, guide design standards, mentor engineers, and implement AI tooling and guardrails for engineering workflows.

Execute and monitor promotional programs for the Lottery business from setup through closeout. Configure offers, validate campaign requirements, maintain launch calendars, coordinate with CRM and Marketing teams, monitor delivery and promotional performance, investigate issues, and report revenue and sales metrics. Improve repeatable operational processes and identify automation opportunities while coordinating multiple stakeholders and timelines.

Supports general litigation and legal risk management across the business. Responsibilities include assessing lawsuits, demand letters, complaints, and legal threats; drafting and reviewing court filings; coordinating with outside and opposing counsel; representing the company in small claims court; supporting regulatory investigations; and providing practical legal guidance to internal teams.

Lead reliability, scalability, and operational excellence of large-scale database platforms across cloud and on-prem. Build automation-first database infrastructure (Kubernetes operators, IaC, GitOps), drive monitoring/SLOs, incident leadership, performance and cost optimization, and partner with application teams on safe schema/migration practices. Mentor engineers and evaluate AI-assisted workflows to improve productivity and reliability.

Lead strategy and programs for leadership effectiveness, designing AI-enabled coaching, learning, simulations, and manager enablement. Partner with senior leaders to scale leadership experiences, build AI copilots, measure manager effectiveness, and align leadership development with business priorities.