Director of Information Systems

Compensation: Competitive compensation based on experience

We Find A Way.

At Crossroads Courier, every delivery matters.

We're looking for a Director of Information Systems to help shape how technology drives growth, efficiency, customer experience, and competitive advantage across our organization.

This is not a helpdesk leadership role. 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.

• 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

• 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

• 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

• Direct partnership with executive leadership
• High visibility and influence across the organization
• Opportunity to shape long-term technology strategy
• Lead AI and innovation initiatives
• Ability to create meaningful business impact
• Collaborative and entrepreneurial culture
• Competitive compensation and benefits package

If you're a business-minded technology leader who enjoys solving complex challenges, driving innovation, and helping organizations grow through technology, we'd love to hear from you.

Crossroads Courier is an Equal Employment Opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex (including pregnancy, sexual orientation, gender identity), national origin, age, disability, genetic information, veteran status, or any other protected status under applicable federal, state, or local law.