What to Expect in Your First 90 Days with a vCISO

Cybersecurity breaches are a growing concern for Irish businesses. A recent report highlighted that over 60% of Irish SMEs experienced a cyberattack in the past year, with significant financial and reputational consequences [1]. For many, the idea of bolstering their cyber defences can feel overwhelming, especially without a dedicated in-house security expert. This is where a Virtual Chief Information Security Officer (vCISO) steps in, offering strategic guidance and practical support. But what exactly happens when you bring a vCISO on board? Understanding the vCISO onboarding process and what to expect in your first 90 days with a vCISO can help you maximise the value of this crucial partnership.

The Initial Assessment: Understanding Your Unique Landscape

The first phase of your vCISO engagement is all about deep understanding. Your vCISO will conduct a comprehensive initial assessment to gain a clear picture of your current cybersecurity posture. This isn't a generic checklist; it's a tailored deep dive into your specific business operations, IT infrastructure, existing policies, and regulatory obligations. For Irish SMEs, this often includes evaluating compliance with GDPR, and increasingly, preparing for the NIS2 Directive, which will impact a broader range of entities [2].

Key areas of focus during this assessment typically include:

• Technical Infrastructure Review: Examining your networks, systems, applications, and cloud environments.
• Policy and Procedure Audit: Assessing existing security policies, incident response plans, and employee awareness programmes.
• Risk Identification: Pinpointing critical assets, potential vulnerabilities, and the specific threats your business faces.
• Compliance Landscape: Understanding your obligations under Irish and EU regulations, such as GDPR, and relevant industry standards.

This initial assessment provides the foundation for all subsequent strategic planning. It helps to identify immediate gaps and long-term objectives, ensuring that the vCISO's efforts are aligned with your business goals and risk appetite.

Quick Wins and Immediate Impact

While the comprehensive assessment is underway, a good vCISO will also identify and implement "quick wins" within the first 90 days. These are high-impact, low-effort improvements that can significantly enhance your security posture almost immediately. They demonstrate tangible value and build confidence in the partnership.

Examples of common quick wins include:

• multi-factor authentication (MFA) Deployment: Implementing MFA across critical systems to drastically reduce the risk of unauthorised access.
• Basic security awareness training: Rolling out initial training modules for employees to address common threats like phishing, a prevalent attack vector against Irish businesses [3].
• patch management Optimisation: Ensuring critical security updates are applied promptly to mitigate known vulnerabilities.
• Review of Access Controls: Tightening permissions and access rights to sensitive data and systems.

These early successes not only improve your security but also help to foster a security-conscious culture within your organisation, preparing the ground for more extensive strategic initiatives.

Strategic Planning and Roadmap Development

Following the initial assessment and the implementation of quick wins, the vCISO will work with you to develop a robust cybersecurity strategy and a clear roadmap. This plan outlines the long-term vision for your security programme, prioritising initiatives based on risk, business impact, and regulatory requirements.

Your strategic roadmap will typically cover:

• Risk Mitigation Strategies: Detailed plans to address identified risks, including technical controls, process improvements, and policy updates.
• Technology Recommendations: Guidance on selecting and implementing appropriate security tools and solutions.
• Compliance Frameworks: A plan to achieve and maintain compliance with relevant regulations, such as those from the NCSC Ireland or the Data Protection Commission.
• Budgeting and Resource Allocation: Recommendations for allocating resources effectively to support your cybersecurity objectives.
• Key Performance Indicators (KPIs): Metrics to measure the effectiveness of your security programme and demonstrate ROI.

This phase transforms the assessment findings into actionable steps, providing a clear direction for your cybersecurity journey. It ensures that your investment in security is strategic and delivers measurable results.

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Ongoing Collaboration and Evolution

The first 90 days with a vCISO are just the beginning of an ongoing partnership. Cybersecurity is not a static state but a continuous process of adaptation and improvement. Your vCISO will become an integral part of your team, providing continuous guidance, monitoring emerging threats, and adjusting your strategy as your business evolves and the threat landscape changes.

This includes:

• Regular Reporting: Providing clear, concise updates on your security posture, progress against the roadmap, and any new risks.
• Incident Response Support: Being on hand to assist with security incidents, from detection to recovery and post-incident analysis.
• Board and Management Briefings: Translating complex technical issues into business language for your leadership team, as recommended by the NCSC Ireland for effective governance [4].
• Vendor Security Management: Helping you assess and manage the cybersecurity risks associated with your third-party suppliers.

This continuous engagement ensures that your cybersecurity defences remain robust and responsive, protecting your Irish SME from evolving threats.

What This Means for Your Business

Engaging a vCISO, particularly in the Irish context, means gaining access to expert cybersecurity leadership without the overhead of a full-time executive. It means moving from a reactive stance to a proactive, strategic approach to security. For Irish SMEs, this translates into better protection against cyber threats, enhanced compliance with regulations like GDPR and the upcoming NIS2 Directive, and ultimately, greater confidence in your digital operations. The first 90 days with a vCISO lay the groundwork for a more secure and resilient future.

Ready to Strengthen Your Security Posture?

Pragmatic Security works with Irish SMEs to build practical, proportionate cybersecurity programmes that protect your business, satisfy regulators, and give you confidence. Whether you need NIS2 compliance support, a vCISO on retainer, or a one-off security assessment, we're here to help.

Book a free 20-minute strategy call today — no jargon, no hard sell, just practical advice from an experienced Irish cybersecurity professional.

Or contact us at [email protected] or call +353 870 515 776.

References

[1] Cyber Ireland. (2023). Cyber Labour Market Report 2023. https://cyberireland.ie/publications/ [2] National Cyber Security Centre (NCSC) Ireland. (n.d.). NIS2 Directive. https://www.ncsc.gov.ie/nis2/ [3] NCSC Ireland. (2022). Cyber Security Baseline Standards. https://ncsc.gov.ie/pdfs/Cyber_Security_Baseline_Standards_Rev_1_2022_Final.pdf [4] NCSC Ireland. (2019). National Cyber Security Strategy. https://www.ncsc.gov.ie/strategy/

Take the Next Step

If whether a vCISO is the right fit for your business is something you're thinking about, the best starting point is a structured conversation.

Book a free 20-minute call with our vCISO team. We work with Irish SMEs across every sector — no jargon, no scare tactics, just clear advice on what to do next.

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