Top Tech Jobs & Startup Jobs in Chicago, IL

Lead delivery across multiple engineering and product teams, plan and track key initiatives, surface risks and dependencies, strengthen Agile practices, use metrics and OKRs to improve predictability, and communicate status to stakeholders to ensure on-time launches.

Monitor and verify accuracy of live e-sports game data feeds in real time, identify and resolve discrepancies, cross-check multiple sources, escalate issues, and collaborate to streamline processes. Maintain knowledge of schedules, rosters, rule changes, and key metrics to ensure contextual data accuracy throughout the season.

Lead AI security strategy and guardrails, design and review AI gateways and tooling, scale InfoSec review processes, reduce AI-driven security noise, drive remediation and investigations, and mentor security and platform engineers.

Lead end-to-end product lifecycle for a content management platform: define strategy, API and architecture, co-own roadmap, prioritize engineering work, enable automation and personalization, collaborate with Engineering, UX, Analytics, and stakeholders, and use data and experimentation to measure and iterate.

Create and publish platform-first social content (graphics, short-form video, carousels) that captures cultural and real-time sports moments. Use trend and performance insights to inform strategy, write on-brand copy, build community engagement, and partner with internal teams to align campaigns and optimize content.

Lead procurement strategy and a team supporting Technology & Product. Partner with senior leaders to source and negotiate enterprise software, cloud, AI, and technology services. Develop commercial models, drive vendor consolidation and license optimization, apply analytics to sourcing decisions, and manage contractual, regulatory, and third-party risk while promoting procurement standards across the enterprise.

Lead and scale day-to-day operations for DraftKings Exchange, managing electronic trading, market monitoring, incident resolution, participant onboarding, and cross-functional initiatives. Drive tooling, analyze market and operational data to improve integrity and performance, support regulatory readiness, and collaborate with Engineering, Product, Regulatory, and Analytics to launch and optimize prediction market capabilities.

Build and run the compliance program for DraftKings' prediction market product. Monitor controls, manage issues, support examinations and audits, translate regulatory requirements into processes and platform changes, develop policies and playbooks (AML/KYC, market surveillance, marketing compliance), and prepare compliance reporting and dashboards.

Lead and scale a casino analytics team to drive data-informed strategy, experimentation, and reporting. Partner with product, data science, and operations to deliver executive insights, build analytical frameworks, and develop high-performing analysts to unlock growth and operational efficiency.

Lead strategy, execution, and growth of non-sports prediction markets (crypto, politics, finance, tech, culture). Own operational processes, launch and monitor markets at scale, optimize performance metrics (engagement, retention, volume, revenue), and partner cross-functionally to drive business outcomes using data-driven decisions and trend identification.