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Director of Information Technology
2 weeks ago
About the Role
CCST seeks an experienced Director of Information Technology & Cybersecurity to lead a regional education agency's (ROE's) technology strategy, cybersecurity posture, and digital infrastructure. This role will shape and secure technology delivery for classrooms, staff, and students across multiple districts—balancing innovation, compliance, and operational excellence.
You'll collaborate directly with ROE and district leaders to drive a modern, secure, and equitable learning ecosystem built on Microsoft 365, Google Workspace, and cloud-first principles.
What You'll Do
Strategic Leadership
- Develop and execute a region-wide technology roadmap aligned with educational goals.
- Provide vision and direction for integrating technology into instruction and operations.
- Champion digital equity, hybrid learning, and secure access for all users.
Infrastructure and Systems Management
- Oversee on-premise and cloud-based environments (Microsoft 365, Google Workspace).
- Maintain enterprise systems (SIS, LMS, ERP) and ensure high availability.
- Drive modernization of network infrastructure and endpoint management.
Cybersecurity & Compliance (Priority Focus)
- Lead cybersecurity strategy and risk management.
- Implement safeguards for student/staff data aligned with CIPA, FERPA, COPPA, and Illinois SOPPA.
- Conduct ongoing vulnerability assessments, incident response, and staff training.
- Partner with consultants and vendors to strengthen blue-team readiness and compliance reporting.
Budget & Resource Management
- Develop and oversee IT budgets; optimize resources and E-Rate opportunities.
- Evaluate and procure cost-effective, scalable solutions supporting instructional tech initiatives.
Consultant & Vendor Management
- Serve as the liaison between external consultants, internal staff, and vendors.
- Manage performance, deliverables, and contract compliance across IT projects.
- Ensure transparent communication between technical teams and ROE leadership.
Support Services
- Oversee remote support operations for multiple sites, staff, and students.
- Manage inventory, software licensing, and service contracts.
Must-Have Qualifications
- Bachelor's degree in IT, Computer Science, or related field (Master's preferred).
- 5+ years in IT leadership roles within K–12 or educational organizations.
- Experience managing Microsoft 365, Google Workspace, and enterprise systems (SIS, LMS, ERP).
- Proven record leading cybersecurity initiatives and compliance frameworks.
- Strong communication, stakeholder, and project management skills.
Nice-to-Haves
- CETL, PMP, CISSP, or comparable certifications.
- Experience with E-Rate funding and K–12 data privacy regulations.
- Background coordinating IT consultants and cross-functional tech teams.
Tech Stack You'll Touch:
Microsoft 365 | Google Workspace | SIS/LMS/ERP platforms | Cloud Infrastructure | Endpoint Management | Security Auditing Tools
Benefits & Perks:
- Annual training/education stipend up to $1000
- Remote-friendly with required customer overlap hours
- Mission-driven, small-team environment with visible impact
Location: Remote (Illinois-based clients; CST hours)
Clearance/Work Authorization: Must be authorized to work in the U.S. (no sponsorship available)
How to Apply:
Quick Apply via Indeed or email
Qualified candidates will be contacted within 5 days for next steps.
EEO Statement:
CCST is an Equal Opportunity/Affirmative Action employer. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, pregnancy, genetic information, disability, protected veteran status, or any other status protected by law.
As a Service-Disabled Veteran-Owned Small Business (SDVOSB), we welcome applicants with military experience and encourage veterans and military spouses to apply.
Job Types: Full-time, Contract
Pay: $ $75.00 per hour
Expected hours: 40 per week
Work Location: Remote