Director of Information Systems & AI Strategy

Crossroads Courier, Inc.; St. Louis (MO); On-site; USD 120,000 - 190,000; Full time

Job summary

Crossroads Courier, Inc. is seeking a strategic Director of Information Systems in St. Louis, MO to shape how technology drives growth, efficiency, and customer experience.

This leadership role collaborates with the President and executive team to align AI, cybersecurity, and innovation with business priorities. Responsibilities include directing technology strategy, budgets, vendors, and MSPs, while creating roadmaps, KPIs, and executive-level reporting.

Qualifications

• 7+ years of IT leadership in a small to mid-sized organization.
• Experience developing technology strategy and long-term roadmaps.
• Strong business acumen and executive presence.
• Cybersecurity, risk management, and business continuity experience.
• Technology budgeting and vendor management experience.

Responsibilities

• Develop and execute our technology and innovation strategy
• Partner with leadership to identify opportunities for growth and competitive differentiation
• Lead cybersecurity, business continuity, and risk management initiatives
• Drive AI adoption and identify high-value use cases across the business
• Manage technology budgets, vendors, contracts, and MSP relationships
• Oversee the Microsoft 365 ecosystem and technology environment
• Create executive reporting, KPIs, and technology roadmaps
• Evaluate emerging technologies that create measurable business value

Skills

IT leadership

Technology strategy

Executive presence

Cybersecurity

Budget management

Microsoft 365

Vendor management

Tools

Zoho CRM

TMS platforms

SaaS applications

Job description

Crossroads Courier, Inc. is seeking a strategic Director of Information Systems in St. Louis, MO to shape how technology drives growth, efficiency, and customer experience.

This leadership role collaborates with the President and executive team to align AI, cybersecurity, and innovation with business priorities. Responsibilities include directing technology strategy, budgets, vendors, and MSPs, while creating roadmaps, KPIs, and executive-level reporting.