Signs You Need a CISO

An honest checklist for growing companies.

Count how many apply to your organization. The more you check, the more urgent the need for security leadership.

Signs checked: 0 / 33

Signs Your Customers Are Noticing

The external pressure is building

Security questionnaires are piling up in someone's inbox Your sales team hesitates before sending security documentation A prospect asked for your SOC 2 report and no one was sure how to respond You've lost a deal because a competitor had a compliance certification you didn't Enterprise customers are requiring annual security reviews that no one knows how to run Your security questionnaire responses rely heavily on last year's answers and best guesses

Signs Your Team Is Noticing

Internal gaps are becoming obvious

The "security person" is actually a senior engineer handling it on top of their day job Your security policy is a document from years ago that still says "Draft" The person who set up the company password manager has since left Onboarding new employees involves broad access grants without clear process Offboarding doesn't happen consistently or quickly Your engineers keep asking about security best practices and no one can give them a consistent answer Security decisions are made ad hoc by whoever has time Someone recently discovered a cloud resource that's been misconfigured for a while

Signs You Notice at 2am

The concerns that keep leaders up at night

You've wondered what would actually happen if credentials were exposed The phrase "we should really do something about security" has come up in multiple board meetings You read about a breach at a similar company and recognized the parallels Your incident response plan is informal at best You're not entirely sure if your backups work because no one has tested them There's a growing concern that your logging and monitoring has gaps You've thought about security more in the last few weeks than in the previous year combined

Signs the Market Is Noticing

External stakeholders are asking questions

Your cyber insurance application raised more questions than you expected Investors are asking about security posture during due diligence A potential acquirer asked about your security program and you had to improvise Your insurance premiums increased and the renewal questionnaire got more complex The board wants a security update at the next meeting and you're not sure what to present Your legal team is asking questions about data handling that no one can answer confidently

Signs the Regulators Might Notice Soon

Compliance is becoming unavoidable

You're handling health data and HIPAA compliance is "on the roadmap" You process payments and PCI compliance remains unclear You're expanding into Europe and GDPR requirements are unfamiliar A customer asked about your data retention policy and you realized you don't have one You're pursuing enterprise clients who require compliance certifications you don't have Compliance frameworks come up in conversation but no one owns them

What Your Score Means

0-5 signs

You're in decent shape

You're either early stage, well-organized, or haven't hit the triggers yet. Worth monitoring, but not urgent.

6-12 signs

Time to get serious

The gap between "we should address this" and "we needed to address this" is narrowing. One customer request or incident could accelerate the timeline.

13-20 signs

Security leadership is overdue

Multiple areas of your business are feeling the pressure. This isn't about compliance checkboxes. It's about reducing real risk before something breaks.

21+ signs

Act now

You've been operating with significant gaps. The good news: you've identified the problem. The better news: this is fixable with the right leadership.

Start planning now to get ahead

The best time to bring in security leadership is before you need it urgently. A fractional CISO can help you build a security foundation now, so you're protected before threats arrive and prepared when customers ask.

What does a Fractional CISO do? Get started