Top Tech Jobs & Startup Jobs in Chicago, IL

Build and manage relationships with VIP players, drive sales and net revenue, identify opportunities using customer and performance data, deliver personalized experiences, follow responsible gaming policies, and resolve escalations with internal teams. The role requires strong relationship-building, customer-focused problem solving, revenue growth knowledge, operational improvement skills, and the ability to obtain and maintain state gaming licenses.

Designs and evolves DraftKings’ regulated prediction-markets exchange, including market data, order entry, matching, clearing, and settlement. Owns the technical roadmap, architecture, scalability, reliability, performance, and operational health of distributed systems. Leads resilience testing, incident improvements, design reviews, mentoring, and cross-functional technical alignment. The role also requires building practical AI tooling and guardrails, integrating with external partners, and balancing compliance, cost, and platform strategy.

Own the strategy and roadmap for fraud risk case resolution platforms, including AI-assisted review, automation, self-service, and case management. Partner with Risk Operations, Engineering, Data Science, Analytics, and Compliance to define scalable workflows, requirements, metrics, auditability, and decisioning processes. Use operational data to improve automation, workload reduction, decision quality, customer outcomes, and compliance across regulated markets.

Execute and monitor promotional programs from setup through closeout, including offer configuration, quality assurance, launch coordination, calendar management, performance tracking, issue escalation, and reporting. Partner with CRM and Marketing teams to align campaign requirements and improve repeatable operational processes. Use data, reporting, and workflow tools to evaluate revenue and sales performance and identify automation opportunities.

Own database reliability, scalability, and operational excellence across cloud and on-premises environments. Build automated Kubernetes-based database platforms, infrastructure tooling, failover and backup systems, and self-healing capabilities. Lead observability, performance optimization, capacity planning, incident response, and safe migration practices. Partner with application teams, leverage AI for operational improvements, mentor engineers, influence architecture, and drive technical strategy for highly available database infrastructure.

Leads data scientists and machine learning engineers developing personalized customer experiences. Sets strategy, roadmaps, and priorities; partners with Product, Engineering, Marketing, Revenue, and Data Science leaders; oversees machine learning systems from design through deployment, monitoring, and optimization; advances MLOps, software engineering, experimentation, and production reliability practices; and manages capacity, resources, technical standards, and team development.

Leads product design for complex platform capabilities and strategic initiatives. Defines product vision, creates scalable experiences and reusable design systems, partners with cross-functional teams and Engineering, influences product strategy, sets quality standards, provides critique, and mentors designers. Requires strong interaction design, systems thinking, communication, storytelling, and experience delivering measurable outcomes across shared platforms, internal tools, enterprise workflows, or multi-user products.

Provides legal and regulatory counsel for DraftKings’ regulated prediction-market exchange and related clearing initiatives. Advises on the Commodity Exchange Act and CFTC regulations, drafts exchange rules and governance materials, supports filings, monitors derivatives-market developments, manages outside counsel, and partners with product, engineering, compliance, finance, and operations teams to launch and operate regulated products.

Prospect and acquire high-value VIP customers, build lasting relationships, and manage regional acquisition strategies. The role includes creating customer events, executing localized promotions, managing revenue and profit plans, supporting compliance and responsible gaming initiatives, and delivering experiences that encourage brand advocacy. Candidates need sales or business development experience with high-value accounts, willingness to travel and work nights and weekends, and eligibility for state gaming and financial licenses.