Cracking the Code: A Buyer’s Guide to Penetration Testing Providers
- Fayyaz Rajpari
- May 13
- 6 min read
Updated: May 28
What CIOs and CISOs need to know before introducing penetration testing into their environment.
Why Penetration Testing Matters?
As cybersecurity threats grow in complexity, companies face a constant barrage of vulnerabilities from both external and internal sources. Penetration testing (or “pentesting”) offers a proactive solution by simulating real-world attacks to identify weaknesses before attackers exploit them. For mid-market companies, penetration testing is especially crucial due to the increasing frequency of targeted attacks aimed at organizations that may not have the same defenses as larger enterprises but still hold valuable data.
Key reasons why penetration testing should be a priority for your organization
Rising Threat Landscape
Cyberattacks have become more sophisticated, and with technologies like AI being used for automated attacks, even small vulnerabilities can lead to massive breaches.
Data Analysis
According to a 2023 study, 43% of all cyberattacks target small and midsize businesses, and the average cost of a data breach exceeds $3 million. Organizations with regular penetration testing had 45% fewer security incidents than those without.
Compliance Requirements
Many industries, such as finance, healthcare, and retail, have strict regulations that require regular security testing, including penetration testing, to meet compliance standards.
Reputation Management
A single security breach can significantly damage a company's reputation, leading to loss of customers, trust, and revenue.
Cost-Effectiveness
Fixing vulnerabilities before they are exploited is far less costly than addressing the aftermath of an attack. Proactively investing in penetration testing can save money in the long run.
Real-World Insights
Penetration testing not only identifies technical vulnerabilities but also highlights how human errors and business processes might contribute to security gaps.
What to Consider Before Introducing Penetration Testing
Understanding Your Attack Surface
Identify your most critical assets—whether it’s sensitive data, customer information, or intellectual property—and determine the scope of testing.
Internal vs. External Testing
Decide whether to focus on external threats (from outside attackers) orinternal threats (from within your organization, such as employee mistakes).
Frequency of Testing
A one-time penetration test is not sufficient, as this is a point-in-time assessment. Consider how frequently testing should occur based on your business, compliance requirements, and industry risks as they evolve.
Remediation Planning
A one-time penetration test is not sufficient, as this is a point-in-time assessment. Consider how frequently testing should occur based on your business, compliance requirements, and industry risks as they evolve.
Testing Methodologies
Penetration testing can be conducted manually or automatically. Understanding the pros and cons of each approach is critical.
10 Key Questions Senior Leaders Should Ask Potential Penetration Testing Vendors
Before selecting a penetration testing vendor, it’s essential to ask the right questions. The following questions will help you assess the vendor’s capabilities, methodologies, and the overall fit for your company.
What is your approach to scoping a penetration test?
Why ask: A clear scope ensures that critical assets are tested and that the vendor understands your business needs and objectives.
What methodologies do you use for penetration testing?
Why ask: Penetration testing can follow different frameworks (e.g., OWASP, NIST).
Understanding the methodology ensures it aligns with your security requirements.
Do you offer both manual and automated testing?
Why ask: While automated testing can be quicker and less costly, manual testing provides a deeper, more nuanced analysis, especially for complex environments.
How do you handle remediation and retesting?
Why ask: Vulnerabilities need to be fixed after they are discovered. Ensure the vendor offers clear remediation guidance and is willing to retest after fixes.
What is your process for reporting findings?
Why ask: A detailed and understandable report is critical for your team to prioritize and act on vulnerabilities. Ensure the reporting process is transparent and actionable.
What certifications and qualifications do your testers hold?
Why ask: Certifications like OSCP, CEH, and CISSP show that the testers are qualified and have the skills necessary to perform a comprehensive penetration test.
What is your pricing model & how do you calculate costs?
Why ask: Understand whether pricing is based on the size of the environment, the scope of testing, or the time involved. This helps you budget appropriately.
Do you provide post-test support or consultation?
Why ask: You want a vendor who will not just perform the test but also support you in understanding and addressing the findings.
How do you ensure minimal disruption to our operations during testing?
Why ask: Penetration testing can sometimes impact business operations. A good vendor will have a plan to minimize downtime and interruptions.
Can you provide references or case studies of similar companies in our industry?
Why ask: Knowing the vendor has experience with companies of similar size and industry gives confidence that they can handle your specific challenges.
The IntelliGuards Difference
At IntelliGuards, we offer intelligence-led penetration testing that combines cutting-edge technology with real-world expertise. Let’s discuss how we can support your cybersecurity goals and protect your business from potential threats.
What is your approach to scoping a penetration test?
IntelliGuards: Our approach to scoping begins with an introductory/discovery call, during which we ask a focused set of scoping questions to understand the client's objectives, environment, and constraints. We then provide a comprehensive scoping document that covers all areas of an organization's attack surface, including External Network, Internal Network, Web Applications, Wireless, Social Engineering, and more. To ensure transparency and accuracy, we use our proprietary scoping calculator to generate a tailored, budgetary quote based on the engagement’s size and complexity.
What methodologies do you use for penetration testing?
IntelliGuards: Our penetration testing approach is grounded in industry-standard frameworks and best practices. We incorporate Tactics, Techniques, and Procedures (TTPs) aligned with MITRE ATT&CK, NIST SP 800-115, OWASP, and guidance from CISA. This ensures consistency, effectiveness, and coverage of real-world attack vectors.
Do you offer both manual and automated testing?
IntelliGuards: Yes. We employ a hybrid testing approach that combines automation and manual efforts. Automated tools are used for external asset discovery (ASM), vulnerability scanning, and compliance mapping. Manual testing is performed for nuanced assessments such as web application penetration testing, social engineering campaigns, and exploit validation to uncover complex logic flaws and business logic vulnerabilities.
How do you handle remediation and retesting?
IntelliGuards: We offer complimentary remediation testing as part of our standard engagement. Once the client has addressed the vulnerabilities identified in the original report, we re-test the affected assets and issue a final report that validates fixes and updates the risk posture accordingly.
What is your process for reporting findings?
IntelliGuards: Our deliverables are designed to cater to both technical and non-technical audiences and include:
Detailed Assessment Report
Executive Summary Report
Penetration Testing Methodology Overview
Attack Path Narratives (when applicable)
Vulnerability Summary and Risk Ratings
Debrief Call: A live walkthrough of the findings and recommendations with our security team
Do you provide post-test support or consultation?
IntelliGuards: Yes. Beyond the complimentary remediation testing, we offer post-assessment support, including:
Security awareness and technical training (e.g., Cyber Incident Tabletop Exercises)
Advisory services such as vSPM (Virtual Security Program Manager), providing ongoing security program oversight and strategy
What certifications and qualifications do your testers hold?
IntelliGuards: Our team includes certified professionals with diverse backgrounds in
penetration testing, system administration, and security governance. Relevant certifications
include:
CISSP – Certified Information Systems Security Professional
OSCP – Offensive Security Certified Professional
CRISC – Certified in Risk and Information Systems Control
CWAPT – Certified Web Application Penetration Tester
CEH – Certified Ethical Hacker v11
CHFI – Certified Hacking Forensic Investigator
CCNA – Certified Cisco Network Associate
MCSE / MCSA – Microsoft Certified Systems Engineer/Administrator
ACE – Palo Alto Accredited Configuration Engineer
What is your pricing model & how do you calculate costs?
IntelliGuards: Our pricing is based on:
Type and scope of the assessment (e.g., External Network, Internal Network, Web Applications, etc.)
Number of assets, endpoints, or applications in scope
Frequency of testing (e.g., one-time, quarterly, annual, etc.)
We provide transparent, line-itemized quotes to help clients understand cost drivers and make informed decisions.
How do you ensure minimal disruption to our operations during testing?
IntelliGuards: We strive to minimize operational impact through:
Testing in staging/test environments when possible
Scheduling work during off-hours or weekends for production systems
Maintaining continuous communication with client stakeholders before, during, and after the engagement to align expectations and address concerns in real time
Can you provide references or case studies of similar companies in our industry?
IntelliGuards: As a cyber risk services provider, we have experience supporting clients across diverse industries and security maturity levels. While client confidentiality prevents us from publicly disclosing names or detailed case studies, references can be made available upon special request under a mutual NDA.
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