Question 1

What cybersecurity decisions actually require CEO involvement vs delegating to IT?

Accepted Answer

CEO must decide: risk tolerance (how much to spend on security vs accept risk), incident response authorities (who can authorize paying ransom, taking systems offline, notifying customers), compliance strategy (which frameworks to pursue—SOC 2, ISO 27001), cyber insurance limits ($1M vs $5M coverage). Delegate to IT/CISO: tool selection (which EDR, SIEM, firewall), technical implementation, day-to-day operations, vendor management. CEO involvement needed when: decision has business impact (spending $100K on security tools affects budget), legal/regulatory implications (breach notification, compliance), or reputation risk (customer notification, media response). Don't micromanage: daily security operations, tool configurations, technical details. Do set strategy: security budget, risk appetite, compliance goals, incident response authorities. Meeting cadence: monthly security updates (15-30 minutes), quarterly risk reviews (1-2 hours), immediate notification for critical incidents.

Question 2

How much should we actually budget for cybersecurity?

Accepted Answer

Industry benchmark: 5-15% of IT budget for cybersecurity (varies by industry—healthcare/finance higher, retail lower). For SMB with $500K IT budget: $25K-$75K annually for security. Breakdown: security tools (EDR, email security, backups—$15K-$30K), security assessments (penetration testing, risk assessment—$10K-$25K), training ($2K-$5K), cyber insurance ($5K-$15K). Minimum viable security (any business): EDR ($10K-$20K), email security ($3K-$10K), backups ($5K-$10K), training ($2K), insurance ($5K-$10K) = $25K-$52K annually. More if: regulated industry (add $50K-$150K for compliance), high-value target (add $30K-$100K for advanced monitoring), large company (costs scale with employees/systems). ROI calculation: average breach costs $150K-$500K, spending $50K annually on security to prevent breach pays for itself if it prevents one incident every 3-10 years.

Question 3

What are the warning signs our cybersecurity isn't adequate?

Accepted Answer

Red flags: cyber insurance application rejected or premiums spiking 50%+ (indicates insurer sees high risk), compliance audits revealing gaps (SOC 2/HIPAA audit finds major deficiencies), staff bypassing security (using personal Dropbox because work tools are blocked/inconvenient), no testing (backups never restored, incident response never practiced), or security team of one (single person knows all passwords, no backup if they leave). Other warnings: can't answer basic questions (who has admin access to what? when did we last patch? where is our data?), multiple near-misses (caught malware infections by luck not monitoring), or regulatory pressure (customers/partners demanding security attestations we can't provide). If you see 3+ of these: immediate security assessment needed ($5K-$15K, 2-4 weeks). Don't wait for actual breach—these are warnings that incident is likely.

Question 4

Should we hire a CISO or use vCISO services?

Accepted Answer

Full-time CISO ($150K-$300K+ salary) makes sense when: 500+ employees, heavily regulated industry (healthcare, finance, defense), frequent audits/compliance needs, or building security team (CISO manages multiple security staff). vCISO ($3K-$10K/month, 10-20 hours/month) makes sense when: under 500 employees, need strategic security leadership but not 40 hours/week, want flexibility (scale up/down as needed), or testing before full-time hire. vCISO provides: security strategy, risk assessments, board reporting, vendor management, compliance guidance, incident response leadership. Doesn't provide: day-to-day security operations (that's your IT team or MDR service). Break-even: vCISO at $5K/month = $60K/year vs full-time CISO at $200K+. For most SMBs: vCISO until you need full-time (usually around 200-500 employees or heavy compliance needs).

Question 5

What's the most important security investment a CEO can make?

Accepted Answer

Cyber insurance with incident response coverage ($1M-$5M limits, $5K-$25K annually depending on revenue/industry). Why: breaches happen despite best security (ransomware success rate is high, human error is inevitable), insurance covers: ransom payment (if you choose to pay), forensics and recovery ($50K-$200K typical), legal fees ($25K-$100K), customer notification ($10K-$50K), business interruption losses. Insurance also provides: 24/7 incident response hotline (know who to call at 2AM), access to forensics experts (included in coverage), legal guidance (breach notification requirements), negotiation support (ransomware payment). Without insurance: breach costs $150K-$500K out of pocket. With insurance: covered minus deductible ($5K-$25K). Additionally: cyber insurance application forces security improvements (insurers require MFA, EDR, backups—implementing these reduces risk even without claim). This single decision—buying cyber insurance—often drives other security improvements and provides safety net when prevention fails.

Cybersecurity for CEOs | Protect Your Business Now

Get your book today!

What you will learn

Speak the Language of Cybersecurity

Protect Your Business from Costly Mistakes

Build a Culture of Cyber Resilience

About the book

Get your copy now!

About the author

Frequently Asked Questions

Need Expert Cybersecurity Guidance?

Data breach trends 2023-2025: What organizations and consumers need to know

Common employee cybersecurity mistakes and how to prevent them

CrowdStrike Outage Analysis: What Happened & What's Next