Senior Director, AI

As the Sr. Director of AI, you will own the direction and day-to-day execution of Odyssey's enterprise AI program. Building on a company-wide AI Academy that has already put AI tools in the hands of nearly 140 people across every division, your mandate is to turn broad adoption into a focused set of proven platform wins and, ultimately, into workflows redesigned around AI.

What You Will Do

Leadership and Team Management: Lead and inspire a cross-divisional network of AI leads, fostering a culture of collaboration, experimentation, and disciplined execution. Technical Strategy and Execution: Set enterprise AI priorities across predictive, agentic, generative, and simulation use cases, aligning the roadmap with business objectives and saying no to the rest.

Why It Might Be a Fit

Currently at Director level or above, with senior management experience, hands-on experience architecting and scaling modern AI systems into production, ideally on a major cloud AI platform (e.g., AWS Bedrock, Azure AI Foundry, or Vertex AI)

Requirements

• Currently at Director level or above, with senior management experience
• Hands-on experience architecting and scaling modern AI systems into production, ideally on a major cloud AI platform (e.g., AWS Bedrock, Azure AI Foundry, or Vertex AI)
• A track record of turning pilots into production platforms with measurable business impact and outcomes
• Proven collaboration across both business and IT functions - equally credible with business unit leaders and with engineering teams, and able to move fluidly between the two.
• Program operating discipline - experience running a real pipeline: intake, prioritization, triage, discard weak ideations early on, and tracking value through production.
• Strong communication skills - able to translate technical reality into plain business language
• Demonstrated ability to lead through influence across a matrixed organization
• Experience in logistics, transportation, freight, or another asset-heavy industry
• Experience standing up a new function from scratch; or experience building an AI or data governance model in a complex organization.

Benefits

• A choice of medical plans with FSA and HSA options
• Dental Insurance
• Vision Insurance
• Company-paid Life and Disability Insurance
• 401(k) Plan with Company Match
• Paid Time Off (PTO) and Company Holidays
• Employee Assistance Program
• Company Health & Wellness Program
• Discounts with Preferred Vendors