Sr. Director, AI

Charlotte, NC

About Odyssey Logistics

Odyssey Logistics is a global logistics and supply chain partner helping businesses optimize performance through fully integrated, end-to-end solutions. We connect transportation, technology, and expertise across a broad network of services including 3PL and 4PL managed services, multimodal and intermodal transport, warehousing, trucking, Jones Act Ocean, and customs brokerage, ensuring goods move reliably, efficiently, and intelligently around the world.

Today, Odyssey supports more than 6,000 customers globally, delivering scalable, data driven solutions across complex supply chains. What started with a single client has grown into a dynamic, evolving organization focused on performance, precision, and long-term partnership.

What Sets Us Apart:

Our work is complex, fast moving, and highly collaborative. Success here requires people who think strategically, operate with urgency, and navigate across functions to solve real business challenges. We value individuals who take ownership, challenge the status quo, and turn insight into action.

Our culture is grounded in five core values: Win Together, Innovate Boldly, Drive Results, Customer Centric, and Guide with Care. These are not just principles; they shape how we make decisions, partner with customers, and show up for each other.

At Odyssey, you are not just part of a company; you are part of building what comes next.

The Role:

Work Model: Hybrid

Work Schedule: Monday – Friday (Regular Business Hurs)

Travel Requirements: Yes – Less than 10% or as work demands

Supervisory Responsibilities: Yes

Reports to: Chief Information Officer

Pay Range: Competitive pay plus bonus plan

*All applicants must be currently authorized to work in the United States. No relocation allowance will be considered unless specifically addressed.

Summary / Primary Role:

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. You will lead a cross-divisional network of AI leads, partner closely with business unit leaders and the technology organization to identify and prioritize high-value use cases and be accountable for governance and for measurable business value. Your technical depth in modern AI, your ability to translate between business and engineering, and your discipline in deciding what to scale will be instrumental to Odyssey's next chapter.

What You’ll Do:

Leadership and Team Management:

Lead and inspire a cross-divisional network of AI leads, fostering a culture of collaboration, experimentation, and disciplined execution.
Set the mandate, rhythm, and accountability for AI leads across operations, commercial, finance, and technology, helping them grow their AI fluency and impact.
Build the long-term internal AI capability program that currently relies on outside partners, by attracting and developing talent aligned with organization goals and values.

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.
Collaborate closely across business and IT functions, partnering with business unit leaders to identify use cases and with the technology organization to build them, delivering high-quality solutions on time and within budget.
Own the enterprise AI governance model – establish processes, sanctioned tools, data handling rules, and use-case review - balancing risk against speed and ensuring humans stay accountable for every AI-assisted outcome.

Product Development and Innovation:

Run a disciplined use-case pipeline with robust criteria, converting the strongest ideas into proven platform wins with measurable business impact - production, not pilots.
Stay hands-on with emerging AI models, tooling, and techniques, incorporating relevant innovations and pressure-testing what is realistically buildable versus hype.
Identify and start the highest-value transformation opportunities - workflows redesigned around AI, not just sped up by it - treating the killing of a weak idea early as a health signal, not a failure.

Stakeholder Engagement and Communication:

Collaborate closely with key stakeholders, including executives and business unit presidents, to gather requirements, prioritize initiatives, and communicate progress.
Report progress and value in the language of business outcomes - dollars and hours, not adoption percentages alone - fostering transparency and alignment across the organization.
Serve as a trusted advisor and subject matter expert on AI, translating technical reality into plain business language to inform decision-making at every level.

What You Bring:

10+ years of relevant professional experience, including a minimum of 5 years of experience in AI, machine learning, or related technologies.
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:

We offer a comprehensive and competitive compensation and benefits package, including:

• 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

At Odyssey, we believe the best ideas come from people with different skills, experiences, and perspectives. We welcome applicants from all backgrounds and evaluate every candidate based on the qualifications needed for the role, while also valuing the unique strengths, curiosity, and fresh thinking each person brings. Our commitment to inclusion helps fuel innovation and enables us to deliver smarter, more creative solutions for our customers. We are proud to be a workplace where everyone is treated with respect, given equal opportunity to succeed, and encouraged to contribute in meaningful ways. All employment decisions are based on merit, without regard to race or ethnicity, religion, color, sex, gender identity, sexual orientation, age, disability, national origin, veteran status, or any other characteristic protected by federal, state, or local law.

Odyssey does not discriminate on the basis of actual or perceived race, color, creed, religion, national origin, ancestry, citizenship status, age, sex or gender (including pregnancy, childbirth and pregnancy-related conditions), gender identity or expression (including transgender status), sexual orientation, marital status, military service and veteran status, physical or mental disability, genetic information, or any other characteristic protected by applicable federal, state or local laws and ordinances.

Visit us at: www.OdysseyLogistics.com/careers

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