vCIO Advisor

vCIO Advisor

About Dymin

Dymin Systems, Inc. is a managed service provider in Urbandale, Iowa, serving small and mid-sized businesses across Central Iowa. Our vCIO service line gives clients a named technology leader for strategy, budgeting, security, and compliance planning.

Role summary

Dymin Systems is hiring a vCIO Advisor to own day-to-day, client-facing vCIO delivery for an assigned group of clients. The Advisor is the named technology-strategy lead for those clients, delivering assessments, roadmaps, budgets, security and compliance planning, and recurring executive reviews.

Core responsibilities

The Advisor owns every recurring client-facing deliverable in the vCIO SOW for an assigned client book.

Strategic advisory and roadmap ownership

• Build and maintain a 12 to 36 month technology roadmap per client, tied to business goals and reviewed at least annually.
• Own the annual technology budget: lifecycle replacement, licensing, security spend, and project forecasting.
• Translate client business changes (growth, acquisition, new location, compliance pressure) into technology decisions and scoped work.

Assessment and risk management

• Run onboarding and annual assessments: infrastructure, Microsoft 365 licensing and tenant health, backup and recovery, identity, endpoint, and network.
• Maintain a living risk register per client with owner, severity, and remediation status; escalate unaccepted risk in writing.
• Map client posture to the relevant framework (CIS Controls v8, NIST 800-171, HIPAA Security Rule, PCI DSS, CMMC) as a gap analysis. Framework mapping only; the role makes no legal or compliance attestations.

Security and compliance program delivery

• Operate Dymin's primary vCIO platform (Cynomi) as the system of record for assessments, policies, and remediation tracking.
• Drive policy, awareness training, incident-response planning, and tabletop exercises to completion, not just to draft.

Executive reviews and client communication

• Lead scheduled executive business reviews with client leadership and prepare the materials.
• Serve as the client's named point of contact for strategy, escalations that are strategic in nature, and vendor and licensing questions.
• Write executive-grade documents: risk assessments, remediation roadmaps, board and leadership summaries.

Delivery coordination and vendor management

• Convert roadmap items into scoped work and hand off to Service Delivery with clear acceptance criteria; verify completion against the roadmap.
• Manage client relationships with third-party vendors (ISP, line-of-business software, telecom, hardware) at the advisory level.
• Flag service delivery failures affecting a vCIO client to the CIO and Service Delivery leadership with specifics.

Account health and growth

• Track deliverable completion, client satisfaction, and renewal risk for the assigned book.
• Identify expansion opportunities (projects, security services, additional advisory scope) and pass them to account management with a scoped recommendation.

Qualifications

Required

• 7+ years in IT, including 3+ years in a client-facing advisory, vCIO, consulting, or IT management role in an MSP or professional-services environment.
• Working depth in Microsoft 365 (Entra ID, Intune, Defender, licensing and SKU design), Windows Server and virtualization, networking, and backup and recovery.
• Working knowledge of CIS Controls v8 and NIST 800-171, and ability to run a gap assessment and turn it into a sequenced remediation plan.
• Demonstrated ability to write executive-quality documents and present to non-technical business owners without losing the technical substance.
• Budgeting experience: lifecycle planning, licensing forecasts, and project cost estimation.
• Comfortable owning a client book of concurrent relationships with recurring deadlines, without daily supervision.

Preferred

• Prior vCIO or fractional CIO experience at an MSP.
• Experience with vCIO or compliance platforms (Cynomi or comparable), PSA tooling (HaloPSA or comparable), and Power Automate or PowerShell for repeatable delivery.
• Exposure to HIPAA Security Rule, PCI DSS, or CMMC framework mapping.
• Vendor and contract negotiation experience.
• Certifications such as CompTIA Security+, Microsoft (MS-102, SC-300, AZ-104), CISSP, or CCSP. Certification is not a substitute for experience.

Competencies

• Writes clearly and decisively; states a recommendation, not just options.
• Holds a line with clients on scope, risk acceptance, and budget.
• Follows a documented process and improves it; does not rely on memory or heroics.
• Escalates early, with specifics, when delivery is at risk.