Director of Information Technology and Cybersecurity

Job Summary
Waterfront Training Solutions (WTS), a Service-Disabled Veteran-Owned Small Business (SDVOSB), is seeking an experienced and highly motivated Director of Information Technology and Cybersecurity to lead the organization's technology, cybersecurity, compliance, and information assurance programs.

This is a hands-on leadership position responsible for maintaining secure, compliant, and reliable information systems while supporting the company's strategic objectives and government contracting requirements. The Director will serve as both a technical expert and mentor, providing leadership, guidance, and training to departmental personnel while fostering a culture of teamwork, accountability, continuous improvement, and professional development.

The ideal candidate is a collaborative leader who values people as much as technology, embraces a servant-leadership philosophy, and is committed to helping others succeed. WTS is seeking a professional who leads by example, works alongside the team, and understands that strong organizations are built through trust, respect, mentorship, and shared success.

Essential Duties and Responsibilities

• Lead and oversee all information technology, cybersecurity, and information assurance activities.
• Serve as the primary owner of the company's cybersecurity, compliance, and information security programs.
• Maintain and manage Microsoft 365, Azure, SharePoint, Active Directory, cloud services, networking infrastructure, endpoint management systems, and cybersecurity tools.
• Lead and manage NIST SP 800-171, CMMC, and cybersecurity compliance initiatives.
• Develop, maintain, and improve cybersecurity policies, procedures, and security controls.
• Maintain and oversee all cybersecurity documentation, including:
• System Security Plans (SSPs)
• Risk Assessments
• System Configuration Baselines
• Plans of Action and Milestones (POA&Ms)
• Security Policies and Procedures
• Ensure proper protection and handling of Controlled Unclassified Information (CUI).
• Manage vulnerability assessments, remediation efforts, incident response, system hardening, and security monitoring activities.
• Support customer audits, government assessments, and compliance reviews.
• Develop and maintain disaster recovery, business continuity, backup, and contingency planning programs.
• Manage technology vendors, software licensing, hardware procurement, and IT budgeting.
• Provide strategic technology and cybersecurity guidance to executive leadership.
• Lead technology modernization and infrastructure improvement initiatives.
• Provide hands-on technical support and troubleshooting when required.
• Train, mentor, and develop IT personnel and departmental staff to strengthen organizational technical capabilities and cybersecurity awareness.

Required Qualifications

• Bachelor's degree in Information Technology, Cybersecurity, Computer Science, Information Systems, or related field, or equivalent professional experience.
• Minimum of seven (7) years of progressively responsible IT and cybersecurity experience.
• Minimum of three (3) years of leadership or management experience.
• Experience supporting Department of Defense (DoD), federal government, or government contractor environments.
• Demonstrated experience implementing and maintaining NIST SP 800-171 security controls.
• Experience supporting CMMC compliance initiatives.
• Experience developing and maintaining SSPs, Risk Assessments, System Configuration Baselines, POA&Ms, and related compliance documentation.
• Strong working knowledge of Microsoft 365, Azure, SharePoint, Active Directory, networking, virtualization, endpoint management, and cybersecurity technologies.
• Excellent written, verbal, organizational, and leadership skills.

Required Certifications

• Security+ CE, CISSP, CISM, CASP+, or equivalent cybersecurity certification.

Preferred Qualifications

• Certified Cyber Professional (CCP).
• Experience serving as an Information System Security Manager (ISSM) or Information System Security Officer (ISSO).
• Experience supporting Defense Industrial Base (DIB) contractors.
• Experience with SPRS, eMASS, RMF, or federal cybersecurity compliance programs.

Security Clearance Requirement

• Active Secret Security Clearance required.
• Must be able to maintain clearance eligibility throughout employment.
• Must be eligible to access and manage Controlled Unclassified Information (CUI).

Leadership and Cultural Expectations

At Waterfront Training Solutions, technical expertise alone is not enough. We are looking for a leader who values teamwork, mentorship, professionalism, accountability, and service.

The successful candidate will:

• Lead with integrity, humility, and professionalism.
• Foster a positive, collaborative, and respectful work environment.
• Demonstrate a strong training and mentorship mindset.
• Invest in the growth and development of team members.
• Communicate effectively with employees at all levels of the organization.
• Maintain a positive, solutions-focused attitude.
• Be willing to support both strategic initiatives and day-to-day operational needs.
• Embrace accountability, continuous improvement, and servant leadership.
• Work alongside the team and contribute to the success of the organization.
• Create an environment where employees feel respected, supported, and empowered to succeed.

The ideal candidate is not only a strong technical professional, but also a trusted advisor, mentor, teacher, and teammate who actively contributes to the success of the organization and its people.

Benefits

Waterfront Training Solutions offers a competitive benefits package, paid time off, retirement benefits, professional development opportunities, and a collaborative team-oriented work environment.

Waterfront Training Solutions is an Equal Opportunity Employer and maintains a drug-free workplace.

NOTE: The salary range for this position reflects the size and structure of WTS as a small SDVOSB, while recognizing the importance of the role, required technical expertise, security clearance, and cybersecurity responsibilities. Compensation will be commensurate with experience, certifications, qualifications, and demonstrated ability to support the company’s mission and growth.

Pay: $125,000.00 - $145,000.00 per year

Benefits:

• 401(k)
• Dental insurance
• Retirement plan
• Tuition reimbursement

Work Location: In person