Small Business Cybersecurity Testing: What You Need to Know to Ensure Your Survival

Apr 26, 2023 | Things You Need To Have

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Explore cybersecurity testing methods for businesses: vulnerability assessments, penetration testing, & red team tests. Stay secure!

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Episode Transcript

In today’s increasingly digital world, cybersecurity is of utmost importance for businesses of all sizes. Determining what that security protects against – or more importantly what it may fail to protect against – is a pretty important step in keeping your data safe. The traditional method – getting hacked – tends to be disfavored among most people today, particularly those who, to put it frankly, do not want to get hacked. Probably because it’s dumb.

For safer ways to test the quality of your cybersecurity, there are a number of options available. In this episode of the Fearless Paranoia podcast, we discuss three different cybersecurity testing methodologies: vulnerability assessments, penetration testing, and red team tests, including what they are, how they’re different, and how they overlap.

Vulnerability Assessments

A vulnerability assessment is the broad scanning of your system looking for certain known vulnerabilities. It is a basic system for identifying, quantifying, and prioritizing the vulnerabilities in a system, network, or application. It is an essential first step in managing and mitigating potential threats to an organization’s digital infrastructure.

By conducting a vulnerability assessment, small businesses can gain a comprehensive, if basic and of limited depth, understanding of their security posture, uncovering weaknesses that could be exploited by attackers, particularly the low-hanging fruit consisting of unpatched vulnerabilities and software that hasn’t been updated.

Vulnerability assessments typically involve automated scanning tools that check systems for known vulnerabilities, although for more significant projects, using an external vendor or an internal team may be appropriate. These tools can identify potential security issues, such as misconfigurations, outdated software, and weak passwords.

Penetration Testing

Penetration testing, also known as “ethical hacking” or “pen testing,” is a more active approach to cybersecurity. While vulnerability assessments focus on identifying potential weaknesses, penetration testing goes a step further by actively exploiting any vulnerabilities they identify, attempting to determine how far a real-world attacker would be able to get into the target system. The test seeks to uncover vulnerabilities that are capable of being exploited before a real attacker does.

Penetration testing can be carried out in various ways, with the pen testers having varying levels of knowledge of the systems they are attempting to breach. Essentially, the main purpose of the pen testers is to breach the defensive perimeter using methods a malicious actor may use and demonstrate all the ways the malicious hacker could not only exploit any vulnerabilities in the defenses but also to what extent or end. As such, a pen tester will attempt to escalate privileges, gain persistence, exfiltrate data, or any other action that helps to establish the nature and extent of any vulnerabilities in the target’s defenses.

Red Team Tests

Red team tests, or red teaming, is an even more advanced and comprehensive approach to cybersecurity. A red team test involves simulating a full-scale, real-world cyberattack against an organization’s systems, processes, and people. This exercise is designed to test the organization’s overall security readiness, including its ability to detect, respond to, and recover from a breach.

To that end, Red Team tests are usually conducted without providing advanced notice to an entire organization, and usually have a specific target in mind, such as a specific document containing particularly important (but usually fake) information).

How The Methodologies Compare

While all three methodologies aim to improve an organization’s cybersecurity posture, they have key differences. Vulnerability assessments focus on identifying weaknesses in a system, providing a baseline understanding of an organization’s security posture. This process is often more passive and relies heavily on automated tools. Given the broad, baseline security information that a vulnerability assessment provides, it should come as no surprise that these exams are now frequently required by insurance companies and vendor contracts.

Penetration testing is a more active and targeted approach, simulating real-world cyberattacks to identify vulnerabilities that may be exploited by hackers, and to what extent. This method provides insight into how well an organization’s security measures can withstand a real attack, and which of their vulnerabilities has the greatest likelihood of allowing a malicious actor to gain the most access to critical systems.

Red team tests are the most comprehensive and thorough, evaluating an organization’s entire security strategy, including its people and processes. This method aims to uncover any weaknesses in a company’s ability to detect, respond to, and recover from a cyberattack, providing the most accurate assessment of an organization’s overall security readiness.

How Expensive Are They?

No comparison of these methodologies would be complete without acknowledging the potentially extreme difference in cost between them. Vulnerability assessments, which tend to be automated and are intended to be a broad-but-limited analysis of your environment, are the least expensive to perform and should probably be conducted at least annually. Penetration testing is more expensive, but to what extent depends largely on the intensity and quality of the testing. Automated solutions are available, but having vendors or internal teams perform the tests will be much more comprehensive (and more expensive). Red teaming usually involves hiring experts to conduct the tests from within a company, although hiring outside vendors is possible as well. Unsurprisingly, red team testing is by far the most expensive to perform and is usually reserved for highly specialized circumstances.


Understanding the differences between vulnerability assessments, penetration testing, and red team tests is crucial for small businesses seeking to improve their cybersecurity posture. Each method offers unique benefits and insights and using them in combination can provide a well-rounded view of an organization’s security strengths and weaknesses.

As cyber threats continue to evolve, it’s essential to remain vigilant and proactive with your cybersecurity efforts. By regularly conducting vulnerability assessments, penetration tests, and red team exercises, organizations can better protect their valuable assets, maintain customer trust, and avoid the costly consequences of a data breach.

We’re here to help make the complex language of cybersecurity understandable. So if there are topics or issues that you’d like Ryan and I to break down in an episode, send us an email at or reach out to us on Facebook or LinkedIn. For more information about today’s episode, be sure to check out Fearless where you’ll find a full transcript as well as links to helpful resources and any research and reports discussed during this episode. While you’re there, check out our other posts and podcasts as well as additional helpful resources for learning about cybersecurity.

We aim…

to make cybersecurity understandable to everyone, in short, digestable bites, and guide you through being able to understand what you and your business need to focus on in order to get the most benefit for your cybersecurity spend.

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