Virtual Chief Information Officer

E-N Computers•Waynesboro, VA

4d•$40,000 - $65,000•Hybrid

About The Position

The Virtual Chief Information Officer (vCIO) owns the technology direction for a portfolio of E·N Computers clients. This role acts as the bridge between a client's business goals and E·N Computers' technical execution, developing a coordinated plan. The vCIO is a strategic leader, not a reactive responder, project manager, salesperson, or engineering replacement. The primary output of this role is to enable clients to make better, earlier decisions with visible consequences before commitments are made. This is a senior, client-facing position responsible for maintaining institutional memory across meetings, projects, and tickets, ensuring clients do not need to repeatedly explain their environment or priorities. The vCIO is the central point of contact who prevents this repetition.

Requirements

8+ years of progressive IT experience, with at least 3 years in a client-facing advisory, vCIO, IT director, or senior consulting role at an MSP, MSSP, or comparable internal IT leadership position.
Demonstrated ownership of a multi-client portfolio or complex internal environment, including roadmap, budget, and vendor decisions.
Working fluency in the Microsoft 365 ecosystem (Commercial and at least exposure to GCC/GCC High), Azure/Entra identity, endpoint management (Intune or comparable), and modern networking (Cisco Meraki or equivalent).
Practical experience advising on at least one major compliance framework: CMMC, NIST 800-171, NIST CSF, SOC 2, HIPAA, PCI-DSS, or SEC Reg S-P.
Strong written communication skills, capable of authoring charters, proposals, roadmaps, and QBR deliverables independently.
Executive presence sufficient to brief owners, CFOs, and outside counsel without an account manager translating.
Comfort framing tradeoffs and communicating "no" or "not yet" with rationale to clients.

Nice To Haves

Direct CMMC Level 2 advisory experience, including SSP authorship and C3PAO assessment preparation.
Familiarity with GCC High migration patterns and commercial implications (licensing, tenant separation, identity).
Experience advising regulated financial services clients (RIAs, broker-dealers) on Reg S-P, FinCEN AML, or comparable requirements.
Industry certifications such as CISSP, CISM, CISA, CCSP, Microsoft MS-102 / SC-100 / SC-401, AZ-104, or equivalent.
Experience operating inside an EOS/Traction-driven business (Rocks, L10 cadence, scorecards).
Familiarity with PSA/RMM toolchains (Halo PSA, NinjaRMM/NinjaOne, ConnectWise, Autotask) at an operator level.

Responsibilities

Own each assigned client's multi-year IT roadmap and prioritization, translating technical work into business impact and framing tradeoffs for deliberate decision-making.
Interpret Account Manager intake charters and produce proposal layers (options, sequencing, phasing, risk framing, dependencies) that precede Statements of Work (SOWs), ensuring decision conversations occur.
Surface architectural, vendor, and operational risks early, guiding technical decisions on infrastructure, cloud (M365 Commercial and GCC High), networking (Cisco Meraki and equivalents), endpoint, identity, and security tooling.
Lead client-facing compliance strategy for frameworks such as CMMC Level 1 and Level 2, NIST SP 800-171, ITAR/EAR CUI handling, SEC Regulation S-P, and FedRAMP-adjacent licensing questions, coordinating with internal compliance specialists.
Lead vendor decisions impacting architecture or roadmap, holding underperforming vendors accountable and framing vendor tradeoffs for client action.
Own Quarterly Business Review (QBR) agenda content, findings, and recommendations, driving strategy and technical discussions, documenting decisions live, and updating initiative trackers within 24 hours.
Advise clients on AI tooling decisions, Copilot licensing, data governance, and acceptable-use posture, framing AI adoption as a sequencing and risk question.
Improve ticket quality by ensuring context is captured before work begins, connecting project work to day-to-day support, filtering unclear requests, and providing clear messaging to Account Managers and engineers.
Engage as an escalation layer when root causes are strategic, recurring, or require architectural/roadmap adjustments, escalating to the President for business-level, contractual, or retention risk issues.