Director of Information Systems

Crossroads Courier•Maryland Heights, MO

2d•$120,000•Onsite

About The Position

We are seeking a Director of Information Systems to help shape how technology drives growth, efficiency, customer experience, and competitive advantage across our organization. This is a strategic leadership position 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.

Requirements

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
MSP management experience
Strong Microsoft 365 knowledge
Ability to connect technology investments to growth, efficiency, customer experience, and competitive advantage

Nice To Haves

Transportation, logistics, healthcare, manufacturing, or multi-site operations
AI strategy and implementation
Microsoft Copilot and AI governance
Zoho CRM, TMS platforms, or other business-critical SaaS applications
M&A integration 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