Director of AI Strategy + Adoption

Job Title: Director of AI Strategy + Adoption
Location: Remote within approved company markets; Chicago-area candidates strongly encouraged
About The Company
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.
Job Summary
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.
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.
Key Responsibilities
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 closely connected to the rapidly evolving AI ecosystem, evaluating new tools and capabilities and determining where they have meaningful application within the business.
Coordinate internal teams, external consultants, vendors, and other partners required to move priority initiatives from concept to measurable business value.
Bring structure, accountability, and momentum to complex cross-functional initiatives in an environment where project ownership often sits alongside employees' day-to-day responsibilities.
Requirements:Education:
Bachelor's degree in Business, Technology, Information Systems, Engineering, Finance, or a related discipline preferred.
MBA or other advanced degree is a plus but not required.
Experience:
7–12 years of experience across management consulting, business transformation, digital transformation, product management, program management, innovation, or related disciplines.
Management consulting or similarly structured advisory experience is strongly preferred.
Demonstrated experience leading cross-functional transformation initiatives from problem definition and process discovery through implementation and measurable results.
Hands-on experience with process mapping, workflow redesign, project/program orchestration, roadmap development, and business-case or ROI evaluation.
Experience coordinating business stakeholders, technical teams, vendors, or consulting partners to successfully implement technology-enabled change.
Experience operating as a hands-on individual contributor or leading a small team; this is not a large-team management role.
Formal AI experience is not required, but meaningful personal or professional experimentation with generative AI and emerging tools is expected.
Skills:
Exceptional structured problem-solving and business judgment with the ability to enter an unfamiliar function, understand how work gets done, identify inefficiencies, and determine where technology can create meaningful business value.
Strong transformation and process-redesign capabilities with the ability to move from current state → opportunity → future-state workflow → implementation → adoption → measurable ROI.
Strong program and product-management discipline with the ability to create roadmaps, establish priorities, coordinate cross-functional teams, manage dependencies, and maintain momentum through execution.
Strong AI fluency and genuine curiosity, with a habit of personally experimenting with emerging tools and thinking critically about how they can change business processes—not simply automate individual tasks.
Strong analytical and financial orientation with the ability to evaluate opportunities based on expected value, establish meaningful KPIs, measure outcomes, and communicate ROI to executive leadership.
Excellent stakeholder influence and facilitation skills with the ability to create alignment across departments and move initiatives forward without relying on direct authority.
Ability to translate effectively between business and technology teams, understanding enough about AI and modern technology to guide solutions without needing to personally engineer them.
Strong change-management and adoption instincts, recognizing that successful AI transformation requires workflow redesign, training, communication, employee engagement, and sustained behavioral change.
Executive-level communication skills with the ability to simplify complex topics, present recommendations, communicate progress, and advise senior leaders on where the organization should invest.
High ownership, curiosity, and learning agility with the willingness to move between strategy and hands-on execution in a rapidly evolving environment.
Preferred Qualifications:
Background in management consulting, innovation consulting, digital transformation, customer experience transformation, or technology-enabled business transformation.
Experience leading smaller, highly hands-on transformation programs where the individual personally drove discovery, orchestration, implementation, and measurement.
Experience developing and prioritizing enterprise use cases based on ROI, feasibility, and business impact.
Demonstrated use of generative AI tools such as Claude, ChatGPT, or similar platforms to improve workflows, conduct analysis, prototype solutions, or increase personal productivity.
Experience developing internal AI champions, centers of enablement, training programs, or other enterprise adoption models.
Exposure to highly analytical or financially oriented businesses is valuable; real estate experience is not required.
Why Join Us
This is an opportunity to become the organization's first dedicated leader focused on turning AI potential into enterprise value.
The foundation is already taking shape: business leaders are identifying high-value use cases, internal Data and Engineering capabilities are established, and an AI ambassador model is being developed across departments. What the organization needs now is someone who can bring those pieces together—prioritize where to focus, redesign how work gets done, orchestrate execution, drive adoption, and prove the value created.
For a hands-on transformation leader who has become genuinely fascinated by AI and wants the opportunity to shape how an organization works in the years ahead, this is a rare opportunity to build tha

Work arrangement
Yes