Virtual CISO (vCISO)

Jobtailor

Naperville (IL)

On-site

USD 140,000 - 200,000

Full time

14 days+

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Job summary

Jobtailor seeks a seasoned vCISO to serve as the trusted security leader for assigned clients in Naperville, IL. You will own and maintain a comprehensive security roadmap, lead executive briefings with CIO/board-level stakeholders, and coordinate with the vCIO team to deliver quarterly reporting.

You will manage patching compliance, vulnerability remediation, and risk acceptance, translating technical risk into business language for executives while leveraging tools such as Huntress,

Qualifications

5+ years in security advisory, CISO, or vCISO roles within MSP/ MSSP environments.
CISSP or CISM certification and ability to translate risk for executives.
Experience identifying revenue opportunities through consultative client work.
Familiarity with NIST CSF 2.0 or similar frameworks; strong documentation.
Experience with Control Map or similar gap assessment methods is a plus.
Knowledge of Autotask, ScalePad, Huntress, Threatlocker, Connect Secure, Datto RMM.

Responsibilities

Serve as the named vCISO and trusted security leader for assigned clients.
Own and maintain a comprehensive Security Roadmap updated quarterly.
Lead executive relationships with quarterly briefings to C-suite/board.
Partner with vCIO team, providing quarterly client reporting.
Conduct quarterly Control Map gap assessments using NIST CSF 2.0.
Identify NRR opportunities and articulate them in business terms.

Skills

VCISO Experience

NIST CSF 2.0 Framework

Client Relationship Management

Incident Response Leadership

Consultative Client Engagement

Education

CISSP

CISM

Tools

Huntress

Threatlocker

ConnectSecure

Datto RMM

Autotask

ScalePad Lifecycle Manager

Job description

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 elevate 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)

Core Competencies

Demonstrates expertise as a vCISO, effectively translating technical risks into business language for executive stakeholders while maintaining compliance with frameworks such as NIST CSF 2.0. Proven ability to identify revenue opportunities and manage security roadmaps, ensuring adherence to patching compliance and vulnerability remediation.

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