Director of AI Strategy + Adoption

Job Title:
Director of AI Strategy + Adoption

Location: Remote within approved company markets;
Chicago-area candidates strongly encouraged

We are an established, privately held real estate development and property management organization with more than four decades of experience building, owning, and operating multifamily communities. Our vertically integrated model gives us a unique perspective: we don't simply develop properties—we operate them, learn from customers and employees, and use those insights to continuously improve what we build and how we work.

We are a highly analytical, financially disciplined organization with a culture focused on efficiency, continuous improvement, and thoughtful growth. As AI creates new opportunities to fundamentally rethink how work gets done, we're building an enterprise capability focused on turning those possibilities into measurable business outcomes.

The Director of AI Strategy + Adoption will lead the organization's efforts to identify, prioritize, and implement high-value AI opportunities across the enterprise. This is a business transformation role—not a technical AI development role
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We're looking for a hands-on transformation leader with the structured thinking of a management consultant and the execution discipline of a strong product, program, or transformation leader. You'll work across departments to understand how work gets done today, redesign processes around what's now possible with AI, prioritize opportunities based on business value, and orchestrate the people, technology, training, and change required to make those solutions real.

You’ll serve as the critical bridge between the business and internal Data/Engineering teams or external technology partners. You won't personally build every solution; you'll ensure the right problems are being solved, the right resources are aligned, initiatives keep moving, employees adopt new ways of working, and results are measured.

The ideal candidate is highly analytical, organized, curious, and commercially minded—with genuine enthusiasm for experimenting with AI and a track record of turning ambiguous, cross-functional opportunities into structured plans and successful outcomes.

• Own the enterprise pipeline of AI opportunities, identifying and prioritizing use cases based on business impact, feasibility, organizational readiness, and expected ROI.
• Partner directly with functional leaders to understand existing workflows, identify friction and low-value activities, and redesign processes to take advantage of emerging AI capabilities.
• Translate ambiguous business challenges into clear strategies, roadmaps, project plans, success measures, and executable transformation initiatives.
• Lead cross-functional AI initiatives from discovery and prioritization through solution development, implementation, adoption, and measurement.
• Serve as the bridge between business teams and internal Data/Engineering resources or external consultants, ensuring business needs are translated effectively and initiatives continue moving forward.
• Build and lead an internal AI ambassador model, enabling employees across departments to identify practical use cases and accelerate responsible adoption within their teams.
• Develop training, enablement, and change‑management programs that increase AI fluency and help employees integrate new capabilities into everyday workflows.
• Establish KPIs and ROI frameworks for AI initiatives, measuring productivity, efficiency, quality, cost savings, employee experience, and other relevant business outcomes.
• Provide executive-level reporting on AI initiatives, adoption, realized value, emerging opportunities, risks, and recommended investments.
• Stay…