Virtual CISO (vCISO)

WEBIT Services•Naperville, IL

5d•Onsite

About The Position

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.

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 Haves

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)

Responsibilities

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.
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
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
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
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
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