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Unpacking the Interview: Penetration Tester

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By: Shelby Welty

December 21, 2020

Unpacking the Interview: Penetration Tester

More than sixty percent of web applications are vulnerable to high- or critical-risk vulnerabilities outside the OWASP top 10 list. For companies, this creates a serious cybersecurity gap. If apps and services contain undetected weaknesses that hackers could exploit to compromise IT environments at scale-enterprises could find themselves dealing with massive data exfiltration or complete system shutdowns. As a result, the role of penetration tester is more important than ever. These IT professionals are responsible for identifying, exploiting, and ultimately remediating infrastructure, platform, and software weaknesses to help companies reduce total risk.

From certifications such as CEH and OSCP to hands-on skills in cryptography, mobile hacking, and vulnerability scanning, penetration testers combine the ethical mindset of white hat security pros with black hat hackers' strategic acumen making them a valuable asset for any IT team.

A challenge for many potential pen testers Is navigating the initial interview — ensuring the talents and training they possess come across clearly to HR managers, existing IT staff, and C-suite members alike. This piece will unpack the penetration testing interview to help prospective pen testers ace the interview and land the job.

Testing, Testing…

As data compliance and regulatory rules evolve across the globe — from California's CCPA to the EU's GDPR, companies can't afford the risk that comes with vulnerable applications, processes, or services. Here's why: Even if organizations are unaware of these issues, they're still responsible for safeguarding customer, staff, and corporate data. This falls under the broader concept of "due diligence," which requires businesses to make every effort possible to secure data sources.

This is the role of penetration testers — to uncover issues that may be hiding in plain sight or buried in complex IT frameworks, understand how they work, and ultimately improve corporate cybersecurity. Understandably, enterprises want to make sure they're hiring the best.

Question 1: What is penetration testing?

Expect this question in any pen-testing interview. It's almost always included as a way to ensure prospective candidates can articulate what they're doing and why it matters. With a host of cybersecurity certifications now available and many that offer overlapping content, this question helps interviewers ensure potential employees are the cybersecurity fit.

When answering this question, it's critical to highlight the difference between vulnerability assessments and penetration testing —while the former focuses on scanning systems for potential weak points, the latter involves a full-scale cyberattack on corporate systems to evaluate key defenses.

It's also worth mentioning the role of different "teams" in the pen testing process: The blue team (defenders), red team (attackers), and purple team (neutral observers).

Question 2: Describe some of the most common pen testing techniques

While the general category of pen testing describes the process of compromising key systems, focused techniques exist to help assess specific security concerns. Five common categories exist:

  • Web application testing
  • Wireless network and device testing
  • Network infrastructure testing
  • Social engineering testing
  • Client-side app testing

The ability to describe both the theoretical and practical application of these techniques is critical for effective pen testing frameworks.

Question 3: Walk us through a network intrusion attack

How does a network intrusion attack happen? While there's no hard-and-fast framework, typical phases include:

  • Reconnaissance

Reconnaissance first involves finding target IP addresses, discovering domain names, and assessing DNS records. Next, attackers — and their pen testing counterparts — typically scan target systems to determine what services are in operation, if any open ports exist, and if any firewalls are in place.

  • Gaining access

Armed with reconnaissance data, pen testers look to gain access by exploiting discovered weaknesses. This might include detected vulnerabilities in existing software that haven't been properly patched or existing processes that provide an opportunity for social engineering to compromise business email accounts.

  • Maintaining access

It's one thing to gain access — it's another to maintain it over time. Here, the goal of pen testers is to evaluate the potential for persistent threats on corporate networks. How long can attacks remain undetected? Is it possible to create network backdoors that circumvent security processes on-demand?

  • Obscuring attack actions

Finally, pen-testing teams need to assess attackers' ability to cover their tracks and leave no trace. If teams can create attacks that aren't easily detected, this speaks to the need for more robust security controls.

Charting a Career in Compromise

As the demand for in-depth penetration testing increases, careers in compromise are expanding. From entry-level roles, such as system admins and SOC analysts, to mid-level ethical hacking, incident responders, and IT auditors to advanced positions including cybersecurity managers and architects, the need for reliable and robust pen-testing can't be overstated.

For prospective penetration testers, this career path starts with common certifications such as CompTIA Security+, CEH, and OSCP. It is bolstered by in-depth, hands-on training in vulnerability detection, exploitation, and remediation.

So, what's the bottom line? Organizations need IT pros capable of thinking like hackers but acting as defenders by compromising — and then enhancing — network, infrastructure, and application security with advanced pen testing tactics and techniques.

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