Chris CashdanStrategic Thinker · Real Estate · Technology & AI

I read the signals of where society is heading, and what they mean for real estate.

I'm driven by two questions: what moves demand in the economy, and where is society heading next? I study how human behavior shapes decisions, and how a single event can ripple through an economy. The pandemic changed how people live and work. That reshaped demand for office towers in central business districts, and with it, the mom-and-pop lunch spot that depended on the people commuting to those offices. It also pushed all of us to rely on technology far more than we were used to. Almost overnight, we worked, met, learned, and shopped through screens. That shift primed the world for generative AI: when ChatGPT arrived in late 2022, people were ready to embrace it. I've built my career on that curiosity: observing how markets behave, running the numbers, and mastering the tools that turn data into real insight, first at Skanska Commercial Development and most recently at GID/Windsor Communities. Today those tools are data and AI, and I use them to connect the granular details of how people live to the bigger picture of where real estate is headed.

See my work →Ask me about AIAbout mePREA AI Presentation
AI Within Development · 2023 PREA Institute
Boston, MA7+ yrs in real estate dataFormer Bronx math teacherEarly GenAI adopter since 2023Speaker: ARES · PREA · USC Gould · USC Lusk →
01 / projects

Selected projects

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Multifamily operations

Assess Sales Skills Performance

Using Snowflake Cortex Code to analyze leasing coordinators' calls and emails, and tie what they say to how their properties perform, to find the sales techniques that actually work.

Multifamily operations

Changing Policies Tracker

A weekly Copilot agent that scans local government sites in every city where our multifamily properties sit, and flags which housing policies are new versus already being discussed.

Multifamily operations

Portfolio Management

A Power BI agent that scores every multifamily property on occupancy, availability, and rent trends, then produces a weekly top 10 list of properties that need attention.

02 / ai in real estate

AI in Real Estate, department by department

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Which tasks AI will replace, what stays human, and the tools worth building in each part of a real estate firm.

03 / faiq

Frequent AI Questions

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04 / thoughts

Continued Thoughts on AI

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05 / references

What colleagues say

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“I had the pleasure of working with Chris Cashdan at Skanska, where I came to know him as an exceptionally knowledgeable, curious, and generous colleague. Chris has a rare ability to connect technology, data, and emerging trends with the strategic challenges and opportunities facing the real estate industry.”
Christopher WestleySVP, Strategic Services, Skanska USA Commercial DevelopmentPartnered with me and my team on technology, business insights, and special projects
“Chris approaches work with curiosity, initiative, and creative problem solving. He takes ownership of challenges and supports associates in building analytical capabilities and developing in their roles. He is a true team player.”
Kyle AudetSVP, Operations, GIDManager
“Chris has an exceptional intellectual curiosity and a passion for creative problem solving. He has a knack for applying new technologies to existing problems to drive better outcomes. On a personal level, he's also a joy to work with and a great team member.”
Joby ByroadeVP, Data & Analytics, GIDManager
“Chris has a profound ability to work collaboratively across a wide variety of business units in a world that is rapidly integrating AI into work flows. His ability to hear a business problem, quickly digest it, and propose a tech-enabled solution is an asset to all who work with him. Along with his individual skills, Chris leverages his background as an educator to empower others to learn new technologies in a thoughtful way.”
Austin LittleVice PresidentPartnered on various AI and data projects