Senior Director of Artificial Intelligence

Compass Group•Chicago, IL

1d•Hybrid

About The Position

Levy is the premier food and beverage operator in the sports and entertainment, convention center, and cultural spaces — present at the biggest moments in North American venue culture, across hundreds of events and millions of fans each year. E15 Group is Levy's analytics and strategy consultancy, embedded with partners from the NFL to MLB to the NBA, translating data into decisions that drive revenue, fan experience, and operational excellence. Together we harness proprietary transaction data at scale, embedded relationships with venue operators and ownership groups, and a consulting team that already speaks the language of both hospitality and analytics. We now seek a Senior Director of AI to lead our AI vision, strategy, and execution. This role will be responsible for identifying, prioritizing, and delivering AI-driven solutions that enhance guest experience, optimize operations, and unlock new revenue opportunities across the business. This leader will operate at the intersection of business strategy, technology and innovation, serving as both a strategic advisor to senior leadership and a hands-on builder of AI capabilities.

Requirements

5+ years of experience in AI, machine learning, analytics, data science or related field
Proven experience developing AI tools and delivering measurable business impact
Strong understanding of modern AI technologies, including generative AI and learning platforms
Experience evaluating and implementing third-party AI solutions
Ability to translate complex technical concepts into clear business value
Excellent communication and stakeholder management skills
Experience building and leading high-performing teams in ambiguous, fast-moving environments
This is an in-office role based in Chicago. Hybrid schedule with 3 days/week in office required

Nice To Haves

Background in hospitality, retail, or high-volume consumer operations
Experience with LLM applications, agentic systems, or AI product development beyond traditional ML
Experience with Claude, Gemini, CoPilot, and/or OpenAI
Familiarity with venue technology ecosystems: POS systems, inventory management, BI platforms
Experience working within or alongside enterprise organizations

Responsibilities

Define and lead Levy’s AI strategy across operations, corporate functions, analytics and partner services
Identify high-impact opportunities where AI can drive efficiency, revenue growth, and guest satisfaction
Build the business case for investments, translate it for executive audiences, and hold the organization accountable to outcomes
Stay ahead of emerging AI trends and translate them into practical business applications
Conduct a comprehensive assessment of Levy’s current AI and data landscape
Evaluate business functions (operations, culinary, supply chain, marketing, finance etc.) for AI opportunities
Develop and maintain a prioritized AI roadmap, including short-term wins and long-term transformation initiatives
Establish success metrics and ROI frameworks for AI initiatives
Lead the design, development, and deployment of AI-powered tools and solutions
Partner with product, engineering, and data teams to build scalable and secure AI systems
Oversee pilot programs and ensure successful transition to production
Drive adoption of AI solutions across business units
Define standards for AI development, deployment, and performance monitoring
Collaborate with senior leadership and business stakeholders to identify needs and opportunities
Develop compelling business cases and proposals for AI initiatives
Evaluate and recommend third-party AI vendors, platforms and partnerships
Lead and manage a high-performing AI team
Act as a key liaison between business, technology, and data