vCIO

We are seeking a  Virtual Chief Information Officer (vCIO) to serve as a trusted technology advisor to our clients’ leadership teams.  You will own the strategic technology relationship for a portfolio of clients, translating business priorities into clear technology roadmaps, investment plans, and risk management decisions. You will help executives understand their technology environment, prioritize improvements, and make informed decisions about security, cloud services, governance, and modernization.  This role requires strong business judgment, executive communication skills, and sufficient technical depth to guide recommendations and challenge proposed solutions.

Client Strategy and Executive Advisory

- Build trusted relationships with business owners, executives, finance leaders, and compliance stakeholders.

- Understand each client’s business model, growth plans, operational challenges, and risk tolerance.

- Lead strategic business reviews focused on business outcomes, technology risks, investment priorities, and progress.

- Translate complex technology issues into clear recommendations, options, costs, and business implications.

- Advise clients on technology decisions involving growth, acquisitions, office changes, business continuity, and operational improvement.

Technology Roadmaps and Financial Planning

- Develop and maintain multiyear technology roadmaps aligned with each client’s business objectives.

- Prepare technology budgets covering recurring services, licensing, infrastructure, cybersecurity, and planned projects.

- Present investment scenarios with clear costs, benefits, dependencies, and consequences of deferral.

- Maintain visibility into asset lifecycles, vendor renewals, technical debt, and upcoming investment requirements.

- Review roadmaps regularly and adjust priorities as business needs change.

Cybersecurity, Risk, and Governance

- Help clients understand and prioritize cybersecurity, data protection, and business continuity risks.

- Work with Venture’s technical and governance teams to turn assessment findings into practical improvement plans.

- Support technology planning related to audits, regulatory expectations, cyber insurance, and client due diligence.

- Advise on technology policies, data governance, vendor risk, and responsible AI adoption.

- Present material risks to client leadership and document decisions, ownership, and accepted risks.

Internal Alignment and Delivery Oversight

- Work closely with Technical Alignment Managers, service delivery, solution architects, project teams, and account management.

- Use technical assessments and service trends to identify strategic issues requiring client decisions.

- Ensure approved initiatives have a defined scope, accountable owner, timeline, and intended business outcome.

- Monitor progress against client commitments and escalate delays or unresolved risks.

- Maintain clear boundaries between strategic advisory, technical design, project delivery, and daily support responsibilities.

Client Growth and Retention

- Identify opportunities where Venture’s services can address a documented business need or technology risk.

- Partner with sales and technical teams to develop recommendations and proposals.

- Build client confidence through consistent follow-through, sound advice, and measurable progress.

- Contribute to Venture’s advisory standards, business review process, and industry-specific service offerings.

Qualifications

- Five or more years of progressive experience in IT consulting, technology leadership, IT management, or a comparable advisory role.

- Experience managing client relationships and presenting recommendations to senior executives.

- Strong understanding of Microsoft 365, Azure, identity management, cybersecurity, infrastructure, and business continuity.

- Experience developing technology roadmaps, budgets, business cases, and risk-based recommendations.

- Ability to manage a portfolio of clients while maintaining reliable follow-through.

- Strong writing, presentation, facilitation, and stakeholder management skills.

- MSP experience is an asset.

- Experience supporting financial services or other regulated organizations is preferred.

- Relevant Microsoft, ITIL, security, governance, or project management certifications are assets.

Measures of Success

- Clients maintain current, approved technology roadmaps and budgets.

- Strategic business reviews produce documented decisions, owners, and next steps.

- Material risks are clearly communicated and tracked through remediation or documented acceptance.

- Client commitments and internal follow-ups are completed on time.

- Clients demonstrate progress against agreed technology and business priorities.

- Strong client retention, executive engagement, and adoption of appropriate recommendations.