Virtual Chief Information Officer (vCIO)

River Run Computers•Glendale, WI

About The Position

The vCIO serves as the primary strategic advisor and account growth leader for a portfolio of managed services clients. The role owns the client relationship, develops and maintains IT roadmaps and budgets, and is accountable for creating and advancing opportunities that drive adoption of River Run's standard services and generate new recurring and project revenue while protecting the technical teams from unsustainable utilization pressure.

Requirements

Bachelor's degree in computer science, information technology, business, or a related field; equivalent experience may substitute for formal education for internal candidates.
Strong experience in IT services, MSP, or related environment in a client-facing advisory role (e.g., account manager, senior engineer with client leadership, or vCIO).
Demonstrated ability to create and manage IT roadmaps and budgets that align technology initiatives with business goals.
Solid understanding of managed services offerings, including maintenance, monitoring, backup, security, and cloud services.
Experience leading or overseeing IT projects from inception through delivery (scope, risk, stakeholder communication).
Excellent communication skills, able to explain technical topics in business terms and build trust with non-technical executives.
Strong business acumen: comfortable discussing budgets, ROI, and trade-offs with owners and leaders.
Consultative mindset with an ability to ask good questions, uncover needs, and connect them to specific services and outcomes.
Relationship-builder who maintains proactive contact and handles difficult conversations with empathy and clarity.
Organized and disciplined in follow-through, documentation, and managing multiple accounts and initiatives.

Nice To Haves

Prior experience in a vCIO, account manager, or similar role within an MSP.
Familiarity with ITIL concepts and service management practices.
Experience with PSA/CRM tools (e.g., ConnectWise) for managing tickets, opportunities, and client data.
Certifications in relevant areas such as Microsoft 365/Azure, security, or project management (e.g., PMP, Prince2) are a plus.

Responsibilities

Serve as the client's main strategic IT contact and trusted advisor for assigned accounts.
Develop, maintain, and communicate short- and long-term IT roadmaps aligned with client business objectives and River Run standards.
Facilitate regular planning and QBR meetings, presenting performance, risks, and recommended next steps.
Build and manage IT budgets with clients, ensuring roadmaps are realistically funded and sequenced.
Evaluate client environments against R-MIT/R-MIT+ and security standards and identify gaps that require remediation or service changes.
Translate business and compliance requirements into clear, actionable technology initiatives.
Identify, qualify, and document opportunities for additional services, security tools, projects, and upgrades that directly support the roadmap and standards.
Own early-stage sales motions (discovery, value framing, "fundable next steps") and partner with Sales/leadership to scope, price, and close opportunities.
Meet agreed-upon targets for activity (QBRs, roadmaps updated), pipeline created, and influenced revenue for assigned accounts.
Collaborate with Technical Services, Security, and Project Management to ensure proposed work is supportable, scoped appropriately, and scheduled realistically.
Provide clear requirements, success criteria, and context to delivery teams and stay engaged through project completion as the client's advocate.
Escalate systemic issues and recurring risks; participate in continuous improvement discussions on offerings and operating model.
Present monthly/quarterly performance reports, including service KPIs, incidents, project status, and roadmap progress.
Maintain consistent weekly touchpoints with key client stakeholders via email, phone, or scheduled check-ins.
Keep CRM and internal systems up to date with roadmaps, opportunities, risks, and key decisions.