Virtual Chief Information Officer (vCIO) - Chicago, IL

Job Responsibilities

• Conduct regular onsite or remote Strategic Business Reviews (SBRs) with client stakeholders.
• Maintain consistent communication and relationship-building touches with clients.
• Ensure high levels of client satisfaction by monitoring feedback, addressing concerns, and following up on unresolved issues.
• Serve as an advocate and escalation point for clients within the organization.
• Develop and maintain strategic technology roadmaps for each client.
• Define and track clear business and technology alignment objectives.
• Aid clients with IT budgeting and cost forecasting.
• Identify and communicate IT risks, compliance requirements, and mitigation strategies.
• Provide thought leadership on emerging technologies and industry trends.
• Collaborate with the Design Desk to prepare technology proposals, solution specifications, and project scopes.
• Review and validate project plans, budgets, and outcomes against client business goals.
• Guide clients in evaluating technology investments through ROI and TCO analysis.
• Conduct scope reviews with clients before the client signs the proposals.
• Coordinate closely with Client Success, Security, and Support teams to ensure alignment across delivery.
• Provide oversight on service and accounting escalations, ensuring issues are resolved to the client’s satisfaction.
• Contribute to training, mentoring, and development of staff.

Job Qualifications

• Bachelor's degree in Business, Computer Science, Information Technology, or a related field; equivalent professional experience may be considered.
• Broad knowledge of IT infrastructure, telecommunications, business applications, and emerging technology trends.
• Experience working with Microsoft environments, network infrastructure, and cloud technologies.
• Understanding of regulatory and compliance frameworks such as HIPAA, PCI, GDPR, and similar standards.
• Demonstrated ability to retain clients by delivering measurable business value through strategic technology guidance.
• Strong project oversight experience with the ability to manage multiple initiatives simultaneously.
• Ability to translate complex technical concepts into clear business language for executive and non-technical stakeholders.
• Excellent communication, presentation, and relationship management skills, with the ability to engage executives and key decision-makers.
• Strong organizational, prioritization, analytical, and problem-solving abilities.
• Business acumen with a consultative approach to client relationship management.
• Self-motivated with a high degree of initiative, accountability, and ownership.
• Ability to work independently while collaborating effectively across cross-functional teams.
• Strong client service orientation, active listening, negotiation, and conflict resolution skills.
• Professional demeanor with the ability to maintain confidentiality and handle sensitive business information.