# Virtual CISO (vCISO) > WEBIT Services · Naperville, United States (Hybrid) · Full-time · Posted 2026-08-03 **Salary:** USD 100,000–130,000 **Workplace:** hybrid **Department:** Sales & Marketing ## Description 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 ## Apply [Apply at WEBIT Services](https://apply.workable.com/webitservices/j/F65DD5FA4F/apply) --- Powered by [Workable](https://www.workable.com)