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Job description
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.
What You’ll Do
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
What We’re Looking For
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
Preferred Experience
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
Why Crossroads Courier?
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.
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Worksite address
st. louis, MO, 63146, US
Who can apply
Review the original listing for work authorization, qualifications and employer requirements.