Continuous Pen Testing: The AI Revolution in Cybersecurity
Cybersecurity leaders have long wrestled with a fundamental challenge: how to stay ahead of evolving digital threats while managing limited resources and expertise. Enter Plainsea, a groundbreaking platform that’s reimagining penetration testing through the power of artificial intelligence.
At the heart of this innovation is Marko Simeonov, CEO of Plainsea, who brings a wealth of experience from the managed security service provider (MSSP) world. His team has identified critical pain points that have plagued traditional pen testing for years.
“The traditional model is very expensive for clients,” Simeonov explains. “You need high expertise, and it’s a costly job. It’s incredibly difficult to hire expert pen testers and even harder to retain them because they get bored easily and want to do interesting work.”
The Fragmented Landscape of Cybersecurity
Testing Pen testing has long been a critical but cumbersome process. Organizations typically rely on annual assessments that provide nothing more than a snapshot of security at a single moment in time. This approach leaves massive gaps in continuous protection. Simeonov and his team recognized that modern critical systems are constantly evolving. New functionalities, updates, and changes occur rapidly, rendering traditional pen testing methods obsolete almost immediately after completion.
“Sure, you can find vulnerabilities,” Simeonov notes, “but your systems won’t remain in the same state. Within months, they’ll start to evolve with new functionalities and changes.”
The AI-Powered Solution
Plainsea’s platform introduces a revolutionary approach to continuous pen testing. Their AI assistant doesn’t replace human expertise but augments it, providing real-time guidance and recommendations throughout the testing process.
Key features include:
- Automated vulnerability data enrichment
- Real-time risk scoring
- Automated reporting
- Compliance-ready checklists
- Continuous testing capabilities
The AI assistant can provide specific steps and recommendations, allowing organizations with limited cybersecurity expertise to conduct more comprehensive security assessments.
Breaking Down Barriers to Entry
Traditionally, building an internal pen testing team has been prohibitively expensive and complex. Plainsea’s platform democratizes this process, enabling organizations of various sizes to implement robust security testing.
“We’re allowing organizations to use our platform without vast experience,” Simeonov emphasizes. “They can now have continuous pen testing in-house at a much cheaper price than hiring third-party providers.”
Flexibility and Customization
The platform offers multiple subscription packages tailored to an organization’s specific needs. A free version allows initial exploration, while proof-of-concept options provide deeper insights. Compliance doesn’t become an afterthought. Plainsea’s platform generates reports that can be customized to meet specific industry requirements, ensuring organizations remain audit-ready.
The Human Element
While AI plays a crucial role, Plainsea understands that human expertise remains irreplaceable. Their subscription model includes human validation hours, ensuring that critical vulnerabilities receive expert attention.
“AI cannot always guide you to finding a critical vulnerability,” Simeonov candidly admits. “That requires creative exploitation, something AI hasn’t fully mastered.”
A New Paradigm for Cybersecurity
Plainsea represents more than just a technological solution. It’s a fundamental reimagining of how organizations approach security testing. By making continuous pen testing accessible, affordable, and intelligent, they’re helping close critical security gaps.
Call to Action
CISOs looking to transform their security testing approach should:
- Request a demo of the Plainsea platform
- Explore the free version to understand its capabilities
- Consider a proof-of-concept to evaluate its potential
Learn more at: https://plainsea.com/
Author’s Note: This exclusive interview was conducted live at the 2025 Black Hat Conference in Las Vegas, providing an unprecedented look into the future of cybersecurity testing.
About the Author
Pete Green is the CISO / CTO of Anvil Works, a ProCloud SaaS company and co-author of “The vCISO Playbook: How Virtual CISOs Deliver Enterprise-Grade Cybersecurity to Small and Medium Businesses (SMBs)”. With over 25 years of experience in information technology and cybersecurity, Pete is a seasoned and accomplished security practitioner.
Throughout his career, he has held a wide range of technical and leadership roles, including LAN/WLAN Engineer, Threat Analyst, Security Project Manager, Security Architect, Cloud Security Architect, Principal Security Consultant, Director of IT, CTO, CEO, Virtual CISO, and CISO.
Pete has supported clients across numerous industries, including federal, state, and local government, as well as financial services, healthcare, food services, manufacturing, technology, transportation, and hospitality.
He holds a Master of Computer Information Systems in Information Security from Boston University, which is recognized as a National Center of Academic Excellence in Information Assurance / Cyber Defense (CAE IA/CD) by the NSA and DHS. He also holds a Master of Business Administration in Informatics.
