Director of Data & Systems
On-site · Chicago, Illinois, United States
Job Summary
Director of Data & Systems to own and evolve Cross Street’s entire technical ecosystem—from infrastructure and physical site systems to data and AI. Build scalable, secure technology stack; define data strategy and ensure a single source of truth for reporting and analytics. Identify and implement AI solutions to improve workflows and productivity; lead a small, high-impact team over time; partner with the executive team to align technology with business strategy. Drive architecture decisions across internal and external tools, oversee company-wide network infrastructure, hardware deployments, and operational technology across sites; ensure reliability, uptime, and security while enabling cross-team collaboration and data-driven decision-making.
Required Qualifications
- 5+ years of experience in engineering, infrastructure, data, systems, or technical leadership roles
- Proven experience building and scaling real-world infrastructure and operational systems
- Strong understanding of networks, hardware environments, cloud systems, data architecture, and analytics
- Experience implementing AI or automation into business workflows
- Ability to operate both as a hands-on builder and strategic leader
- Comfort in a fast-moving, startup-style environment with evolving priorities
- A systems-oriented mindset—you solve root problems, not surface issues
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