Head of IT & AI Strategy

Orange Barrel Media; Kentucky; On-site; USD 120,000 - 180,000; Full time

Job summary

Orange Barrel Media in the United States is seeking a senior IT leader to run the Information Systems function. You will manage the IT team day to day and shape where our technology and systems will be in two to five years, not just today.

A core part of the role is leading AI adoption across OBM—setting usage guidelines, training staff, and evaluating tools worth adopting. You’ll also own vendor relationships, budget, security, and business continuity across OBM's offices.

Qualifications

• 10+ years of progressive IT experience with team leadership.
• Track record building and executing an IT strategy or roadmap at a growing company.
• Experience evaluating and deploying AI tools in a business setting.
• Experience managing external systems and vendor contracts.
• Strong training and communication skills for non-technical employees.
• Solid IT security fundamentals and business continuity planning.
• Bachelor's degree in Information Technology, Computer Science, or related field.

Responsibilities

• Lead the Information Systems team and set priorities across OBM offices.
• Own IT operations, reliability, and rapid issue resolution.
• Build and maintain a multi-year IT roadmap aligned with growth.
• Define future-state architecture and present recommendations to leadership.
• Manage IT budget, vendor negotiations, and renewals.
• Drive company-wide AI guidelines, training, and adoption tracking.
• Maintain inventory of external systems and tools; assess consolidation opportunities.
• Ensure IT security and business continuity for critical systems.

Skills

IT Leadership

Team Management

AI Adoption

IT Strategy

Vendor Management

IT Security

Training & Communication

Education

Bachelor's degree in IT/CS/Business

Job description

Orange Barrel Media in the United States is seeking a senior IT leader to run the Information Systems function. You will manage the IT team day to day and shape where our technology and systems will be in two to five years, not just today.

A core part of the role is leading AI adoption across OBM—setting usage guidelines, training staff, and evaluating tools worth adopting. You’ll also own vendor relationships, budget, security, and business continuity across OBM's offices.