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
Skills Required
- 5+ years of experience in a security advisory, CISO, or vCISO role
- Experience within an MSP or managed security services environment
- Relevant security certification (CISSP, CISM, or equivalent)
- Proven ability to translate technical risk into business language for executives and board-level audiences
- 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
What We Do
You rely on technology every day, but is it really working for you? Maybe it feels like IT is just one more thing holding your business back. You’ve dealt with recurring issues, sluggish support, missed opportunities, and rising security risks. You’ve invested time and money, but it’s not translating into real progress—or a competitive advantage. You want more than a vendor. You want a technology PARTNER who listens, understands your goals, and helps your team work smarter, not harder. You want proactive strategies, not just reactive fixes. And you want technology that supports growth, aligns with your business plan, and stays ahead of threats—not one that’s constantly behind. That’s where your journey with us begins. At WEBIT Services, we work with organizations that are ready for something better. We start by understanding how your business operates, what outcomes matter most to you, and what’s standing in your way. Then, we build a long-term strategy that transforms your IT from a cost center into a value driver. You don’t need more tools. You need the right ones—backed by an employee-owner team that’s invested in your success. Let’s have a conversation about what’s not working, where you want to go, and how technology can help you get there.
