Virtual CISO (vCISO)

WEBIT SERVICES is a Managed Services Provider in Naperville, Illinois, servicing customers in the Western Suburbs of Chicago. WEBIT Services is looking for an experienced vCISO to join our team.

Are you a security leader who's just as comfortable in the boardroom as you are in risk management? WEBIT is looking for Virtual CISO to serve as a trusted, named security advisor for our managed security clients. A person who can translate technical risk into business strategy and help executives make confident, informed decisions about security posture.

This is a strategic, client facing leadership role. You won't be doing hands-on remediation (that is what our service desk is for) --- instead, you will own the big picture: security, planning, compliance posture, executive relationships, and driving real business value through structured, evidence-based assessments.

What You'll Do

Client Security Advisory

• Serve as the named vCISO and trusted security leader for your assigned clients.
• Own and maintain a comprehensive Security Roadmap, updated quarterly based upon assessment findings
• Build and lead executive relationships, including quarterly briefings with C-suite and board members as appropriate

• Partner closely with the vCIO team, providing quarterly reporting for each client.

Driving Growth Through Control Map Assessments

• Conduct quarterly Control Map gap assessments using the NIST CSF 2.0 framework

• Identify Net Revenue Retention (NRR) opportunities and articulate them in clear business language
• Convert identified gaps into ScalePad Lifecycle Manager initiatives

• Keep the vCIO team in the loop on client changes tied to NRR projects

Security Posture Oversight

• Own patching compliance KPI's (95%+ within 14 days for OS, 90%+ within 7 days for third party, 100% of critical patches within 72 hours)
• Monitor vulnerability remediation SLA adherence (95%= target)
• Ensure full tool coverage across managed assets: Huntress, Threatlocker, ConnectSecure, and Datto RMM

Client Reporting

• Deliver monthly security posture reports in plain business language--no raw scanner output
• Lead quarterly Security Roadmap briefings with executive stakeholders
• Provide a weekly internal posture summary to WEBIT leadership

Documentation

• Keep thorough records of interactions, decisions, and action items in Autotask
• Document NRR opportunities with clear business justification
• Track risk acceptance decisions and their compensating controls

Escalation & Incident Response

• Acknowledge security incidents within 1 hour
• Coordinate response efforts with the service desk, keeping communication clear
• Immediately escalate breaches, regulatory exposure, or media -sensitive incidents to the COO

Requirements

• 5+ years of experience in a security advisory, CISO, or vCISO role - ideally within an MSP or managed security services environment
• A relevant security certification (CISSP, CISM, or equivalent)
• Proven ability to translate technical risk into business language for executives and board-level audiences
• A track record of identifying and closing revenue opportunities through consultative client facing work
• Working knowledge of the NIST CSF 2.0 framework or comparable compliance framework
• Strong documentation habits and follow through

Nice to Have

• Experience with Control Map or similar gap assessment methodologies
• Familiarity with Autotask, ScalePad Lifecycle Manager or similar PSA/ITSM tools
• Hands on exposure to Huntress, Threatlocker. Connect Secure, or Datto RMM
• Experience leading incident response tabletops or post incident reviews
• Background across multiple compliance frameworks (SOC 2, HIPPA, PCI-DSS, ISO 27001)

What Makes You Great at This

• Strong executive presence
• A consultative, relationship first approach to selling
• Methodical, process driven mindset
• Calm, sound judgement when incidents escalate
• High accountability and documentation discipline
• The ability to balance strategic advisory work with revenue goals

Why This Role Matters

As vCISO you'll close the gap between security risk and real business decisions for WEBIT's managed clients. You'll keep the security posture viable, actionable and understandable -- giving them a trusted named leader they can count on. It's a role where strategic thinking and genuine client relationships go hand in hand.

Benefits

Company Paid Day-1 Health Insurance for employee

Company Paid AD&D Insurance

Company Paid LTD& STD Insurance

Unlimited PTO after 90 days of employment

Employee Assistance Program

Dental Insurance

Vision Insurance

401k Plan

Life Insurance

Additional Information

Position is Full time salaried

Salary range $100,000 - $130,000/yr

Employee Ownership Eligible after 1 year of service