Overcoming Cybersecurity Challenges with Offensive Security Solutions

How do you do more with less in cybersecurity where you must constantly stay one step ahead of attackers? The easy answer is you turn to the tools and techniques of those attackers to test and improve defenses - and evaluate the ROI on your existing controls.

The Attack Surface Keeps Expanding

As businesses embrace digital transformation and move to the cloud, traditional, perimeter-based defenses are no longer sufficient. Today’s software-defined infrastructure is blurring the lines between network and compute, introducing new layers of risk that on-premise systems of the past never had to manage. Modern applications rely on microservices, APIs, and dynamic cloud environments, which continuously evolve. This evolution is a joy for developers but a headache for security as cloud platforms introduce new forms of exposure, and organizations must adapt quickly to identify and manage risks across distributed infrastructure.

Even with robust internal checks, vulnerabilities such as server misconfigurations, XSS, and outdated software continue to plague organizations, leaving sensitive systems open to exploitation. Cobalt’s State of Pentesting 2024 found that misconfigurations and broken access controls remain top risks across industries. 

Security Teams Face Talent Shortages and Mounting Workloads

While having to deal with the challenge of an expanding attack surface, security teams are simultaneously struggling with finding enough people to address the issues. Good security experts are difficult to come by. The 2023 ISC2 Cybersecurity Workforce Study found that 67% of organizations reported a shortage of cybersecurity professionals, while 92% cited critical skills gaps—particularly in cloud security and AI-related roles​. 

This isn’t new. 

This has been a topic broadly covered for years; including in 2017, when 40,000 jobs for information security analysts were going unfilled, and in 2015 when Yahoo! (remember them?) complained about not being able to find talent.  

Talent shortages slow down vulnerability remediation. In Cobalt’s pentesting data, it often took over 30 days to resolve vulnerabilities like outdated software, adding to the security debt that companies carry year after year. While many are hoping AI can solve some of these gaps, code writing co-pilots also lead to additional pain; AI tools are accelerating software production but also introducing more flaws, further burdening already stretched security teams.​

So what? 

With an increasing attack surface to secure and fewer hands to help, many teams are starting to look at security prioritization differently.  

Fact 1: Automated tools and defenses - while necessary - can miss subtle flaws that human malicious actors exploit. 

To deal with this fact and to be more efficient with time and resources, companies are turning to an offensive security approach to strengthen and prioritize their defensive efforts. And they are looking to scale this effort.

What does Offensive Security mean in practice?

Offensive Security is a proactive cybersecurity strategy focused on identifying and exploiting system, network, and application vulnerabilities by mimicking real-world attack methods, tools, and techniques. The goal is to discover security weaknesses before malicious actors can exploit them, enabling organizations to strengthen their defenses. Unlike defensive security, which focuses on prevention and mitigation, offensive security actively tests the effectiveness of those defenses by adopting the mindset and tactics of attackers.

Key Components of Offensive Security:

• Pentesting: Simulates real-world cyberattacks to identify exploitable vulnerabilities in applications, infrastructure, or systems.
• Attack Surface Management (ASM): Monitors the continuously expanding perimeter of cloud services, APIs, and digital assets to detect vulnerabilities proactively​​.
• Red Teaming: A more advanced form of testing where security experts perform stealth attacks to assess how well an organization detects and responds to intrusions.
• Dynamic Application Security Testing (DAST): Automated testing plays a crucial role by analyzing applications as they are updated to ensure a continuous view of the risk posture of the application in between human-led pentest engagements.
• Advanced Cybersecurity services: including digital risk assessments to understand what data is available on the internet including in social media, public git repositories, and on the dark web.
• Rapid Feedback Loops: through all offense security efforts, findings must be routed to the resolving team quickly to ensure security

Offensive security blends human expertise with automated tools to identify subtle, hard-to-find weaknesses. These offensive methodologies integrate automated testing with collaborative workflows, enabling faster detection and remediation of vulnerabilities across the attack surface​. This method complements defensive strategies, providing an additional layer of assurance by validating that existing security controls work as intended.

Organizations increasingly rely on offensive security approaches to stay ahead of rapidly evolving threats,   shifting from a reactive stance to a proactive one. This allows them to anticipate and address vulnerabilities before attackers exploit them, enhancing resilience and minimizing risk.

In 2023, GigaOm recognized Cobalt as the only Outperformer leading the PtaaS market. Check out this report to learn more about the pentesting market and what sets Pentesting as a Service (PtaaS) apart as well as the common factors buyers use to evaluate PtaaS providers. 

Cobalt is constantly looking at the market from the practitioner's perspective and asking how we can help teams do more with the challenges they are facing. In 2024, Cobalt partnered with GigaOm to dig deeper into our Offensive Security Testing approach and how we help support companies looking to build and scale their offensive security efforts. The GigaOm eBook, CxO Decision Brief: Offensive Security Testing and Pentest as a Service - Inside Cobalt’s Proactive Cyber Defense details the challenges we are seeing and how we help. 

In Closing

In today’s evolving cybersecurity landscape, staying ahead of threats demands both strategic prioritization and operational efficiency. As attack surfaces grow and talent shortages, as well as workload pressures, persist, offensive security approaches—like pentesting, red teaming, and attack surface management— are necessary to keep ahead. By combining human expertise with automation, offensive security not only identifies vulnerabilities but also ensures defenses are tested, validated, and optimized continuously. As more organizations turn to solutions like Cobalt, they can proactively address risks, streamline compliance, and improve resilience. Ultimately, the shift toward offensive security empowers security teams to do more with less, driving stronger outcomes amidst complexity. Ready to get started? Let’s connect and show you why we are the leader in this space.