Sr vCIO

Entertimeonline; United States; Remote; USD 120,000 - 190,000; Full time

Benefits offered by this job

Competitive compensation

Training and certifications

Collaborative culture

Growth opportunities

Job summary

Dynamic Quest seeks a strategic, client-facing vCIO to align technology with business goals, develop IT roadmaps, and drive long-term client success. You will partner with Client Success, Service Delivery, and Security teams to provide proactive guidance across infrastructure, cybersecurity, compliance, and digital transformation initiatives.

This high-visibility role requires executive communication and strong technical acumen, with emphasis on building lasting client relationships and

Qualifications

• 7+ years of IT leadership, consulting, or vCIO/vIT Director roles in MSP/IT services.
• Strong background in IT infrastructure, cloud, networking, and cybersecurity.
• Experience delivering strategic IT roadmaps and executive presentations.
• Experience in regulated or compliance-driven environments (CMMC, NIST, HIPAA).
• Proven ability to manage multiple client relationships simultaneously.

Responsibilities

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

Skills

Executive-level communication

Technical acumen

Client relationship management

Strategic IT planning

Stakeholder management

Job description

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 bothexecutive-level communication skills and strong technical acumen, with a focus on building lasting client relationships and identifying opportunities to enhance service delivery and growth.

Requirements

Client Strategy & Advisory

• 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

Technology & Security Alignment

• 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

Account Growth & Value Creation

• 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

Operational Alignment

• 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

Qualifications

• 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

Preferred Qualifications

• 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)

Work Schedule

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.

Summary

Why Dynamic Quest?

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