Sr vCIO

Dynamic Quest is seeking a strategic, client-facing Virtual Chief Information Officer (vCIO) to serve as a trusted advisor to our clients. This role is responsible for aligning technology with business objectives, developing IT roadmaps, and driving long-term client success.

The vCIO partners closely with Client Success, Service Delivery, and Security teams to ensure our clients receive proactive, value-driven guidance across infrastructure, cybersecurity, compliance, and digital transformation initiatives.

This is a highly visible role requiring both
executive-level communication skills and strong technical acumen
, with a focus on building lasting client relationships and identifying opportunities to enhance service delivery and growth.

• Serve as the primary strategic technology advisor for assigned client accounts
• Develop and present IT roadmaps, budgets, and lifecycle planning aligned to business goals
• Lead recurring Quarterly Business Reviews (QBRs) and strategic planning sessions
• Translate complex technical concepts into business-focused recommendations

• Provide guidance on infrastructure, cloud, networking, backup, and disaster recovery strategies
• Advise clients on cybersecurity best practices
  , risk mitigation, and governance frameworks
• Support clients operating in regulated environments (e.g.,
  CMMC, NIST 800-171, HIPAA, CJIS
  )
• Partner with internal Security and Operations teams to ensure alignment between strategy and execution

• Identify opportunities for service expansion, optimization, and modernization
• Collaborate with Sales and Client Success teams on proposals and strategic initiatives
• Ensure clients understand and realize the full value of Dynamic Quest services

• Act as a liaison between clients and internal technical teams
• Ensure roadmaps are actionable and aligned with Service Delivery capabilities
• Monitor client health, satisfaction, and risk areas, proactively addressing concerns

• 7+ years of experience in IT leadership, consulting, or vCIO/vIT Director roles within an MSP or IT services environment
• Strong background in IT infrastructure, cloud platforms (Azure preferred), networking, and cybersecurity
• Experience developing and delivering strategic IT roadmaps and executive-level presentations
• Demonstrated experience supporting clients in regulated or compliance-driven environments (CMMC, NIST, HIPAA, etc.)
• Proven ability to manage multiple client relationships simultaneously
• Excellent communication, presentation, and stakeholder management skills

• Experience in a Managed Services Provider (MSP) environment
• Familiarity with Microsoft ecosystem (M365, Azure, security stack)
• Relevant certifications (e.g., CISSP, CISM, ITIL, Microsoft, or similar)

This position supports U.S. clients and requires availability aligned with standard business hours. Occasional travel may be required for client meetings and onsite engagements.

Dynamic Quest is a growing MSP delivering Managed IT, Security, and Service Desk solutions to a diverse client base. We are committed to a culture of accountability, innovation, and client success.

• Competitive compensation and bonus structure
• Company-paid training and certification opportunities
• Collaborative, high-performance culture
• Opportunity to make a direct impact on client success and company growth