Title: Director of Data & Systems 

Location: Chicago  

Reports to: President / Leadership  

About Cross Street  

At Cross Street, we’re reimagining real estate from the ground up. We’re modern, human, and  unapologetically ambitious. More than just leasing apartments or selling homes, we collaborate  with developers to bring thoughtful buildings and memorable brands to life—places that feel as  good as they look. We lead with hustle, heart, and real data, balancing creativity with strategy to  drive results that matter. As we grow nationwide, we’re building a company that runs on clean systems, strong infrastructure, and forward-thinking technology.  

We’re hiring a Director of Data & Systems to own and evolve the backbone of how Cross  Street operates. This role goes beyond software and analytics—you will oversee the full  technology ecosystem across the company, including infrastructure, networks, hardware,  physical site systems, data architecture, and AI enablement. This isn’t just about maintaining  systems—it’s about building the operational and technical foundation that will define how we  scale. If you’re someone who thinks in systems, moves fast, and wants to help shape what an  AI-native real estate company looks like, this is your moment.  

Your Mission 

As Director of Data & Systems, you’ll be responsible for designing, building, and scaling Cross  Street’s entire technical ecosystem—from infrastructure and physical site systems to data and  AI. You’ll create the systems that power decision-making, streamline operations, support office  and property infrastructure, and unlock new ways of working across the company. This is a  builder role at its core, with a mandate to future-proof how Cross Street operates in an increasingly AI-driven world.  

Key Responsibilities  

Infrastructure, Networks & Systems  

• Design and maintain a scalable, secure, and high-performing technology stack.  
• Own system architecture decisions across all internal and external tools.  
• Oversee company-wide network infrastructure, connectivity, hardware deployments, and physical site technology systems.  
• Ensure reliability, uptime, security, and long-term durability of all technical systems and infrastructure.  
• Manage and standardize device management, office hardware, and operational technology across sites.  
• Continuously evaluate and implement technologies that improve performance, scalability, and resiliency.  

Data Strategy & Management  

• Build and own Cross Street’s data infrastructure and architecture.  
• Define how data is collected, structured, stored, and accessed across the company.  
• Create a single source of truth for reporting and analytics.  
• Enable teams to make faster, better decisions through clean, accessible data.  

AI & Automation  

• Identify and implement AI solutions that improve workflows and productivity.  
• Move the company from manual processes to automated, intelligent systems.  
• Stay ahead of emerging AI capabilities and translate them into real business impact.  
• Partner with teams to integrate AI into everyday operations.  

Internal Tools & Efficiency  

• Build and optimize internal tools that support leasing, sales, marketing, and operations.  
• Eliminate friction in workflows and improve cross-team collaboration.  
• Continuously identify opportunities to increase efficiency through technology.  

Leadership & Strategy  

• Partner with the executive team to align technology with business strategy.  
• Set technical standards, infrastructure policies, best practices, and long-term roadmap.  
• Hire and lead a small, high-impact team over time.  
• Act as a thought partner on how technology shapes the future of the company.  

In 1 Month, You Will...  

• Get fully immersed in Cross Street’s current tech stack, tools, workflows, and physical  site infrastructure across all teams.  
• Audit existing infrastructure, networks, hardware, data flows, and systems to identify  gaps, inefficiencies, and risks.  
• Map how data is currently collected, stored, and used across the business.  
• Assess office and property technology environments, including connectivity, hardware, and operational systems.  
• Identify immediate opportunities to improve performance, reliability, security, and  usability of internal systems.  
• Align with leadership on priorities across infrastructure, platform, data, and AI initiatives.  

In 3 Months, You Will...  

• Begin implementing a more scalable, reliable technical architecture across the company.  
• Establish a clean, centralized data layer that supports reporting and decision-making. 
• Improve and standardize network, hardware, and site infrastructure across offices and properties.  
• Build or improve internal tools that streamline workflows across leasing, sales, and  operations teams.  
• Launch initial AI-driven workflows that meaningfully improve efficiency (not  experiments—real usage).  
• Define standards for how systems, devices, and infrastructure are built, documented,  secured, and maintained.  
• Partner with leadership to integrate data and technology into day-to-day  decision-making. 

In 1 Year, You Will...  

• Have built a scalable, modern technical infrastructure supporting Cross Street’s national growth.  
• Own a clean, reliable, and actionable data ecosystem used across every team.  
• Have standardized and improved network, hardware, and site infrastructure across all operational locations.  
• Have embedded AI into core workflows across the business, driving measurable  efficiency gains.  
• Be recognized as the technical, systems, and data backbone of the company.  
• Have built and led a high-leverage team supporting infrastructure, systems, data, and  internal tools.  

What We’re Looking For  

• 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.  

Why Join Cross Street?  

• Competitive Compensation: Base salary + performance incentives  
• Generous Perks: Paid time off, Health Benefits, more  
• Real Impact: You’ll define how technology, infrastructure, data, and AI power an entire company  
• Modern Environment: Build with flexibility and the tools you actually want to use  
• Collaborative Culture: We move fast, work together, and keep it fun  
• Future-Focused: Help shape what an AI-first real estate company looks like