vCIO

About the Opportunity

We are seeking a strategic Fractional Virtual CIO (vCIO) to provide executive-level IT management and rigorous cybersecurity compliance oversight for a core client engagement, with potential expansion across our internal portfolio. This position focuses strictly on high-level IT infrastructure stabilization, strict compliance governance, and help desk leadership rather than hands-on engineering.

This role is tailored for an established IT leader who operates an active consulting portfolio and is equipped to manage a rigorous compliance transformation under tight project momentum.

What You Will Do

• Cybersecurity & Compliance Certifications: Take immediate leadership of the organization's compliance architecture. Oversee, implement, and lead the environment through the end-to-end preparation, audit remediation, and certification process for CMMC Level 2 or 3 .

• NIST Security Implementation: Translate NIST framework standards into concrete, actionable security controls and operational implementations, directly closing gaps identified in recent audits.

• Roadmap Execution: Drive an active 90-day cybersecurity roadmap, including patch deployment governance and the administrative oversight of critical endpoint management and encryption tools ( Microsoft Intune, BitLocker, and BitWarden ).

• Help Desk Management & Mentorship: Direct and mentor an existing managed service provider (MSP)-style help desk team of 4 to 5 members, establishing performance discipline and optimizing operational workflows.

• Executive Presence & Advisory: Serve as the chief technical advisor to C-suite and board-level stakeholders, translating technical risks and compliance mandates into clear business growth strategies.

• Vendor Governance: Oversee external technology vendor relationships, managing service level agreements (SLAs), licensing, and contractual compliance.

What We Are Looking For (Must-Haves)

• Advanced Compliance Credentials: A documented history of successfully implementing, leading, and securing certified compliance for CMMC Level 2 or 3 environments.

• Practical NIST Expertise: Proven experience moving beyond high-level NIST compliance theory into specific, practical security implementations and framework alignments.

• IT Leadership & MSP Background: Extensive experience serving as a vCIO or IT Director, with a strong background overseeing tiered help desk operations within an MSP or shared-services environment.

• Microsoft Technology Stack Oversight: Deep administrative and governance familiarity with the Microsoft tech stack, explicitly including Microsoft Intune endpoint management and BitLocker full-disk encryption.

• Executive Communication Skills: Exceptional soft skills with a proven ability to manage vendor expectations and communicate risk postures clearly to non-technical executive stakeholders.

• Local Requirements: Must reside within the Chicagoland area to facilitate minimal, occasional onsite client visits.

Compensation & Structure

• Hourly pay ranges from $80-$100/hour , commensurate with senior executive compliance experience.

• Timeline: Immediate start required to maintain critical project momentum.