Virtual Chief Information Officer

The Virtual Chief Information Officer (vCIO) serves as a strategic technology advisor to Proven IT clients. This role bridges business strategy and technology execution by developing IT roadmaps, driving strategic planning sessions, identifying risk, and ensuring technology investments align with client business goals.

Key Responsibilities

Strategic Leadership

• Develop and maintain multi-year IT roadmaps aligned with client business goals
• Lead quarterly and annual strategic business reviews (QBRs/BRs)
• Provide budgeting guidance, forecasting, and lifecycle planning
• Identify technology gaps, risks, and opportunities

Client Relationship Management

• Serve as the primary strategic advisor for assigned accounts
• Build trusted relationships with executive stakeholders (CEO, CFO, COO, etc.)
• Translate technical initiatives into business outcomes
• Ensure consistent communication of IT strategy and progress

Business & Financial Alignment

• Develop annual IT budgets and technology investment plans
• Present ROI analysis and cost-optimization strategies
• Align technology initiatives with operational efficiency and revenue growth

Risk & Compliance Oversight

• Conduct risk assessments and maturity evaluations
• Guide clients on cybersecurity posture and compliance frameworks
• Collaborate with security and operations teams to remediate risks

Internal Collaboration

• Work closely with Service Delivery, Project Management, Sales, and Engineering teams
• Identify upsell and cross-sell opportunities aligned with client strategy
• Provide clear documentation of client environments, goals, and roadmaps

Key Performance Indicators (KPIs)

• Client satisfaction and retention
• Roadmap adoption and strategic alignment
• Recurring revenue growth within assigned accounts
• Budget adherence and lifecycle management
• Reduction of unmanaged risk and technical debt

Required Qualifications

• 7+ years of progressive IT leadership experience
• Experience in managed services (MSP) or multi-client environments preferred
• Strong understanding of cybersecurity, cloud, infrastructure, and business systems
• Proven ability to communicate technical concepts to non-technical executives
• Experience with IT budgeting and financial planning

Preferred Qualifications

• Bachelor’s degree in IT, Business, or related field
• ITIL, CISSP, CISM, or similar certifications
• Experience with compliance frameworks (NIST, CIS, HIPAA, SOC 2, etc.)
• Experience leading digital transformation initiatives

Physical Requirements 

• Sit for prolonged periods at a desk and use a computer.
• Travel to client sites (up to 25%); must have valid driver's license and reliable transportation.
• Lift and carry up to 35 pounds (e.g., laptops, equipment).
• Enter and work in confined spaces such as server closets when needed.
• Use hands/fingers for typing, writing, and handling IT equipment.

Benefits

GROUP HEALTH INSURANCE:  After a 30-day waiting period, full-time employees (who work at least 30 hours per week) and their dependents, are eligible to enroll in health benefits utilizing the Cigna network. Health options include a choice of 2 PPO plans or a High Deductible Health Plan with employer contributions to a Health Savings Account (HSA). In addition, Dental benefits are available as well as a Vision PPO plan utilizing the EyeMed network. Proven also offers voluntary worksite benefits including critical illness, hospital indemnity, accident coverage, short-term disability insurance, supplemental life and pet insurance. Additional offerings include an employee discount program, home and auto insurance services and commuter/transit FSA.

EMPLOYER PROVIDED LIFE/AD&D INSURANCE:  After a 30-day waiting period, Proven IT provides a flat $25,000 Life Insurance benefit, administered by BlueCross BlueShield, to all full-time employees (who work at least 30 hours per week). Accidental Death & Dismemberment (AD&D) benefit payments are determined based on the type of loss incurred and are payable up to the full Life Insurance benefit amount. Life and AD&D Insurance coverage amounts are reduced at ages 65, 70 and 75.

EMPLOYER PROVIDED LTD: Long-Term Disability (LTD) insurance is an employer-provided benefit and provides protection from loss of income in the event that an employee is unable to work due to illness, injury, or accident for a long period of time.  The elimination period is 90-days, and the maximum benefit is 60% of covered payroll up to $6000/month. This benefit is paid entirely by Proven IT and has no cost to the employee.

EMPLOYEE ASSISTANCE PROGRAM: All employees may utilize the Disability Resource Services through BlueCross BlueShield of Illinois to assist themselves and their immediate family with convenient resources to help address emotional, legal and financial issues. Telephonic counseling and web-based services are available as well as a limited number of geographically accessible face-to-face sessions.

401K PLAN: All employees are eligible after 120 days of service to contribute on either a pre-tax or post-tax (Roth) basis to the 401K plan, administered by Principal Financial Services. Proven offers an employer match equal to 100% of the first 3% of deferrals plus 50% of the next 2% of deferrals. 

FINANCIAL ADVISORY SERVICES:  Proven IT partners with Merrill Lynch to offer financial advisement to all employees. Merrill Lynch financial advisors are available to assist employees at no cost, with their 401k and retirement questions.  

PERMISSIVE TIME OFF POLICY: Proven provides a competitive paid time off policy for all full-time regular employees after a 90-day waiting period. Proven IT empowers their employees to work with their managers and team to coordinate all time off. Managers may impose a limit to requests for time off based on performance and tenure.

PARENTAL LEAVE: Proven IT offers a generous parental leave policy for new parents. After 24-months of employment, Proven provides full-time regular employees with 90-days of paid Maternity leave and 10-days of paid Paternity leave. Employees with less than 24-months of service may take the same amount of unpaid time off.

FITNESS CENTER:  Proven IT offers a free on-site fitness center at the Tinley Park headquarters office location to all employees 24/7 Monday through Sunday. Employees utilize the gym equipment at their own risk.

Proven IT is an Equal Opportunity Employer. We are committed to creating a diverse and inclusive workplace and welcome applicants from all backgrounds. All employment decisions are based on qualifications, merit, and business needs. If you need assistance or accommodation during the hiring process, please contact us.

This job description reflects management’s assignment of essential functions; it does not prescribe or restrict the tasks that may be assigned.