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The Art of CTO Security Assessment Checklist is a free 34-control security posture checklist across six categories — authentication and access control, data protection, application security, infrastructure security, monitoring and logging, and compliance and governance — with each control tagged to OWASP Top 10, SOC 2, GDPR, HIPAA and ISO 27001, reporting completion per category and per framework.

Where are our security gaps?

A posture score across every domain with a prioritised checklist.

About 20 min · Assessment · Free

About this toolWhy it matters, common mistakes, FAQ

Where Are The Gaps You Have Stopped Noticing?

Security debt accumulates quietly and is usually discovered by someone else — a pentester if you are lucky, an attacker or a customer's security questionnaire if you are not. The cost of finding it yourself is always lower.

Effort concentrates where the team is already comfortable, usually application security, while identity, secrets handling and third-party access go unexamined. Attackers do not respect the boundary of what you enjoy working on.

Questions CTOs ask

What does a security posture assessment cover?
A full security posture assessment covers network security, application security, access controls, data protection and incident readiness. This checklist covers 34 controls across six categories — authentication and access control, data protection, application security, infrastructure security, monitoring and logging, and compliance and governance — each tagged to OWASP Top 10, SOC 2, GDPR, HIPAA and ISO 27001. It reports completion per category and per framework with open critical and high-priority items called out. It is a coverage checklist rather than a ranked findings report, and it does not cover SAST/DAST, SSO, data classification or tabletop exercises.
How do you prioritize security vulnerabilities?
Prioritize vulnerabilities using a risk-based approach that considers exploitability (is there a known exploit in the wild), impact (what data or systems are exposed), and exposure (is the vulnerable component internet-facing). CVSS scores provide a starting baseline, but context matters more — a medium-severity vulnerability on a public-facing authentication endpoint is higher priority than a critical vulnerability on an isolated internal tool. Focus remediation efforts on the intersection of high impact and high exploitability.

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