Caesars Entertainment

Director, Business Transformation & AI

Caesars Entertainment$150K — $180K *
Business Services
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • Bachelor’s degree in a related field required.
  • 10+ years of leadership experience in business transformation or strategy.
  • Demonstrated success in leading organizational change.
  • Strong ability to bridge business needs and technical capabilities.
  • Working fluency with AI focused on business applications.
  • Proven influence and stakeholder alignment skills at executive levels.
  • Excellent written and verbal communication skills.

Responsibilities

  • Own adoption of AI and new methodologies across departments.
  • Coach teams on practical AI use for daily operations.
  • Redesign core processes to incorporate AI benefits effectively.
  • Organize institutional knowledge into usable resources.
  • Simplify access to legal and contractual knowledge.
  • Research new opportunities for business growth using AI.
  • Enhance decision-making capacity for senior leaders.

Benefits

  • Collaborative work environment with the central IT team.
  • Opportunity to lead transformational change within the organization.
  • Access to cutting-edge AI and technology tools.
  • Development of personal leadership skills and influence.
  • Engagement in meaningful industry innovation and impact.
Full Job Description

Job Summary:

The Director of Business Transformation & AI leads how Olympia Development works, decides, and grows through the practical use of artificial intelligence and emerging technology. This is a business leadership role, not a technology role. Working in close partnership with Ilitch Companies’ central IT organization — which owns the enterprise technology, platforms, and AI direction — this position is responsible for translating that capability into real change inside ODM: improving how work gets done, how knowledge is captured and used, how risk is identified, and how leadership makes decisions.

The role demands a leader who can champion change, challenge legacy thinking, and drive meaningful evolution across the business — someone with the energy, conviction, and passion to move an organization forward, not simply to deploy tools.

Key Responsibilities:

Lead Adoption and Change Management:
  • Own the adoption of AI and new ways of working across ODM’s departments.
  • Teach and coach the team on practical, everyday use of AI, building fluency from the ground up.
  • Turn new tools into lasting habits, recognizing that most initiatives fail on behavior change, not technology.

Drive Workflow Transformation:
  • Identify where ODM should change how it operates, not simply where tools can be added.
  • Redesign core processes to capture real gains rather than bolting AI onto existing workflows.
  • Prioritize the highest-value opportunities and sequence the work so results are visible.

Own Knowledge Management:
  • Organize ODM’s institutional knowledge — deal structures, partnership terms, entitlement history, construction lessons, and vendor experience — into a resource the team can find and reuse.
  • Turn fragmented information across files and systems into accessible business intelligence.
  • Ensure the business's accumulated experience becomes a durable organizational asset rather than knowledge trapped in files and individuals.

Lead Legal, Contract, and Risk Intelligence:
  • Make legal and contractual knowledge — development agreements, leases, contracts, and incentive documents — far easier to find, summarize, and act on across the business.
  • Support faster, more reliable contract review, lease abstraction, and document comparison.
  • Help leadership identify legal, contractual, and operational risk earlier, before it grows.
  • Partner with the legal team and outside counsel to improve both efficiency and insight.

Champion Innovation and New Value:
  • Research and pursue new opportunities the business has not previously had the tools to take on.
  • Lead applied innovation on high-impact industry problems, including faster and more accurate construction cost estimating.
  • Bring forward creative, well-vetted solutions that create competitive advantage, not just efficiency.

Amplify Leadership Capacity:
  • Help senior leaders spend less time on administrative and routine analytical work and more time on judgment, relationships, negotiation, and decision-making.
  • Increase the organization’s capacity to evaluate opportunities and reach sound decisions without adding senior headcount.
  • Strengthen leadership decision-making through faster, clearer synthesis of complex information.

Ensure Responsible Governance:
  • Partner with central IT and the Director of AI Strategies to ensure AI is used responsibly and securely within ODM.
  • Establish clear, business-aligned standards for the use of AI with confidential deal, legal, and financial information.
  • Align ODM’s adoption with enterprise-wide technology direction and standards.

Required Knowledge, Skills and Abilities:

  • Bachelor’s degree in related field required.
  • 10+ years of progressive leadership experience in business transformation, strategy, operations, consulting, innovation, or a related discipline.
  • Demonstrated success leading organizational change and driving adoption of new processes or technology across multiple functions.
  • Strong business judgment with the ability to translate between business needs and technical capability; deep technical or data-science credentials are not required.
  • Working fluency with AI and emerging technologies, with a clear focus on business application over technical depth.
  • Proven ability to influence and align stakeholders across departments and at the executive level.
  • Excellent written and verbal communication, including the ability to brief and persuade senior leadership.

Preferred Knowledge, Skills and Abilities:

  • Advanced degree preferred.
  • Experience in real estate development, construction, hospitality, or a comparably complex, project-driven industry preferred.

Core Competencies:

  • Champions change and challenges legacy thinking with conviction and credibility.
  • Brings genuine energy and passion for moving the organization forward.
  • Strong communication and executive presence.
  • High emotional intelligence, with the ability to influence without direct authority.
  • Sets priorities and drives results, with a strong bias for action.
  • Translates complexity into clarity for decision-makers.
  • Builds trust and collaborates effectively, including with central IT and across functions.
  • Exercises sound judgment and discretion with sensitive and confidential information.

The above is intended to describe the essential job functions, the general supplemental functions and the essential requirements for the performance of this job.  It is not to be construed as an exhaustive statement of all supplemental duties, responsibilities or nonessential requirements.  Olympia Development has the right to change, modify, suspend, interrupt or cancel in whole or in part any job functions outlined in a job description at any time and without advance notice to the employee.

All items listed above are illustrative and not comprehensive.  They are not contractual in nature and are subject to change at the discretion of Olympia Development of Michigan.

About Caesars Entertainment

Little Caesars makes and delivers the food products. They offer products that are available for shopping online. Their customers' inquiries are addressed through phone, email, and online applications.

Caesars Entertainment Careers

Join the vibrant team at Caesars Entertainment, the pinnacle of entertainment and hospitality, where your career journey is as thrilling as the experiences we offer our guests. As a leader in the industry, Caesars Entertainment provides unparalleled job opportunities, fostering a culture of leadership, diversity, and innovation. Work You’ll Do At Caesars Entertainment, you’ll be part of a community that thrives on excellence and the spirit of hospitality. Our commitment to diversity training ensures an inclusive environment where everyone’s contributions are valued. You’ll work alongside a team of professionals dedicated to redefining the future of entertainment and guest services. Explore a variety of employment paths from casino operations to corporate functions, each offering a chance to innovate and lead. Caesars Entertainment is not just a company; it’s a place where you can shape your future and propel your career to new heights. Join Our Market-Leading Team Step into a role within Caesars Entertainment and join a market-leading team that sets the standards in the global entertainment industry. Our professionals enjoy benefits that support both personal and professional growth, including advanced training programs and leadership development opportunities that prepare you for the next steps in your career. Internship Programs Kickstart your career with Caesars Entertainment through our internship programs. Gain invaluable industry insights and hands-on experience in a dynamic environment. Our internships offer a unique blend of learning and working, ideal for cultivating the skills and knowledge necessary for a successful career in the entertainment and hospitality sectors. Innovative Work Drive innovation as part of the Caesars Entertainment team. Our employees are at the forefront of industry trends and technology, creating memorable experiences for our guests and setting benchmarks in the market. Your work will directly contribute to the company’s legacy of exceptional service and pioneering entertainment solutions. Career Development Future-proof your career at Caesars Entertainment with our vast array of development opportunities. From personalized training sessions to networking events, we provide the tools to enhance your skills and expand your professional network. Whether you’re refining your interview techniques or polishing your resume, Caesars is committed to your growth and development. Join Our Team Search open positions that match your skills and interests. We are continuously hiring and looking for passionate, curious, and creative team players who are ready to take on new challenges. Stay Connected Keep up to date with career tips, insider perspectives, and industry-leading insights—all from the people who make Caesars Entertainment a leader in the entertainment industry. Job Alert Emails Customize your subscription to receive job alerts, the latest news, and insider tips tailored to your preferences. Discover the exciting and rewarding career opportunities that await at Caesars Entertainment. Explore the possibilities with Caesars Entertainment, where your career is part of a larger story of success, innovation, and leadership. Join us and create your own path in the world of entertainment and hospitality.
Learn more about Caesars Entertainment
Size
23,000 employees
Market Cap
$8.8 billion
Industry
Net Income
-$1.7 billion
Founded
2009
5 Year Trend
+60.7%
Revenue
$3.4 billion
NASDAQ

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