Executive IT & AI Strategy Leader

Crossroads Courier; St. Louis (MO); On-site; USD 140,000 - 190,000; Full time

Job summary

Crossroads Courier is seeking a Director of Information Systems to shape how technology drives growth, efficiency, customer experience, and competitive advantage across our organization.

This is a strategic leadership role that partners directly with the President and executive team to determine how technology, AI, cybersecurity, and innovation can help Crossroads Courier operate more effectively and differentiate itself in the marketplace.

Qualifications

• 7+ years of IT leadership experience 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.
• Strong Microsoft 365 knowledge.
• Ability to connect technology investments to growth, efficiency, customer experience, and competitive advantage.

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

Cybersecurity

Budgeting

Vendor management

Microsoft 365

AI adoption

Executive reporting

Tools

Zoho CRM

TMS platforms

Microsoft Copilot

Job description

Crossroads Courier is seeking a Director of Information Systems to shape how technology drives growth, efficiency, customer experience, and competitive advantage across our organization.

This is a strategic leadership role that partners directly with the President and executive team to determine how technology, AI, cybersecurity, and innovation can help Crossroads Courier operate more effectively and differentiate itself in the marketplace.