Director of AI Strategy & Solutions

Compass Group, North America; Chicago (IL); On-site; USD 140,000 - 200,000; Full time

Benefits offered by this job

Medical

Dental

Vision

Retirement Plan

Flexible Time Off

Job summary

Levy Sector in Chicago seeks a Director of AI to shape and execute the AI vision across operations, analytics, and partnerships. You will define strategy, assess current AI maturity, and lead the delivery of scalable AI solutions.

You will partner with product, engineering, and data teams, drive ROI, and manage a high-performing AI team in a fast-paced environment. This in-office role requires 3 days/week on site.

Qualifications

• 3+ 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

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 for AI opportunities and develop a prioritized AI roadmap
• 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 stakeholders to identify needs
• 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 liaison between business, technology, and data

Skills

AI strategy

Analytics

Machine learning

3+ years AI

Third-party AI evaluation

Business value translation

Team leadership

In-office Chicago

Tools

Claude

Gemini

CoPilot

OpenAI

Job description

Levy Sector in Chicago seeks a Director of AI to shape and execute the AI vision across operations, analytics, and partnerships. You will define strategy, assess current AI maturity, and lead the delivery of scalable AI solutions.

You will partner with product, engineering, and data teams, drive ROI, and manage a high-performing AI team in a fast-paced environment. This in-office role requires 3 days/week on site.