vCIO (Virtual Chief Information Officer) (Chicago, IL)

Job Description The vCIO establishes and maintains strategic relationships with client leadership, providing guidance on technology roadmaps, budgeting, and business alignment. The role focuses on reducing risk, improving business outcomes through technology, and serving as a trusted advisor and advocate for clients. Job Responsibilities Client Engagement 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. Strategic Planning & Alignment Develop and maintain strategic technology roadmaps for each client. Define and track clear business and technology alignment objectives. Assist 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. Solution Design & Oversight 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 Internal Collaboration 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. Support cross-department initiatives to deliver outstanding customer service. Governance & Administration Maintain documentation including client files, SBR notes, and roadmap records. Ensure compliance with company policies and procedures. Perform additional responsibilities as assigned. Job Qualifications Education & Experience 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. Skills & Competencies 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. Job KPI’s # of SBRs with clients completed # of Clients with Overdue SBRs (Target 0) # of Clients without a Scheduled SBR (Target 0) # of Opportunities Overdue (Target 0) # of Findings needing review # of clients with Roadmap Ready # of Logged Client Engagement Calls # of Logged Client Onsite Visits Client satisfaction scores, survey results, or retention…