AI Strategy & Solutions, Director

AI Strategy & Solutions Director

We are a private real estate investment and development group with a diverse portfolio across multifamily, life sciences, retail, hospitality, and industrial. We are committed to leveraging technology to drive smarter decision-making, operational efficiency, and value creation. We are seeking an AI Strategy & Solutions Director to lead the integration of artificial intelligence across our business functions.

The AI Strategist will be responsible for identifying, designing, and implementing AI-driven initiatives across investment, asset management, property operations, development, and corporate functions. This role bridges strategy, technology, and real estate expertise to create competitive advantage and position the firm as a forward-thinking industry leader. The role will focus on driving AI across all our asset classes and business lines with a focus on our Hospitality portfolio and our Life & Annuity Reinsurance business.

Key Responsibilities

• Strategic AI Roadmap: Develop and execute a comprehensive AI strategy aligned with company objectives in acquisitions, development, asset management, leasing, property management, and corporate support functions.
• Data & Insights: Partner with data teams to structure and leverage internal and external data sources for predictive analytics and decision support.
• Operational Efficiency: Identify opportunities to streamline workflows through AI and automation tools.
• Investment & Market Analysis: Implement AI models to improve deal sourcing, market forecasting, risk assessment, and portfolio optimization.
• Vendor & Tool Selection: Evaluate, recommend, and oversee partnerships with AI platforms, technology vendors, and consultants.
• Change Management: Educate and train cross-functional teams on AI capabilities, adoption, and ethical considerations.
• Governance & Compliance: Ensure AI initiatives adhere to industry regulations, data privacy standards, and responsible AI practices.
• Development: Lead the hands-on design, development, and deployment of AI solutions, ensuring the ability to translate high-level strategy into technically sound, practical implementations.
• Relationships: Collaborate closely with cross-functional teams—including Operations, Finance, Investments, Legal, and IT—to deeply understand business needs and identify high-impact AI opportunities. Building strong, trust-based relationships with key stakeholders across the organization to ensure alignment, adoption, and measurable business value from AI initiatives.

Qualifications

• Bachelor's degree in Business, Computer Science, Data Science, Real Estate, or related field; advanced degree preferred.
• 7–10+ years of professional experience in strategy, technology, data analytics, or consulting; experience in real estate strongly preferred.
• Proven track record of leading AI or data-driven projects from strategy through implementation.
• Strong understanding of machine learning, natural language processing, and data visualization as applied to business strategy (not necessarily hands-on coding).
• Familiarity with real estate financial modeling, acquisitions, and asset management processes.
• Excellent communication and change management skills; ability to translate technical concepts into business value.
• Entrepreneurial mindset with a passion for innovation and continuous improvement.

Lightstone offers our employees a comprehensive and competitive benefits program inclusive of:

– Paid time off for vacation and sick leave – Health, dental, and vision insurance, and wellness programs – 401(k) and Roth retirement plans – Flexible spending accounts (medical & dependent care) – Life and AD&D insurance with options for supplemental employee, spouse, and child – Long-term and short-term disability insurance – Commuter spending accounts (transit and parking) – Tuition assistance and employee assistance program – Corporate discount programs – On-site mother's room – Office perks such as lunch, fruit, drinks, and snacks

Offered salary commensurate with experience, plus bonus