A Roadmap for Becoming a Penetration Tester in 2023

Few areas of cybersecurity measure up against penetration testing in terms of importance and excitement. This activity boils down to finding flaws in computer systems so that organizations can address them proactively and forestall real-world attacks.

A pentester worth their salt should have outstanding tech skills, be a social engineering guru, and have enough confidence to try and outsmart seasoned IT professionals working for large corporations. Pentesters are often referred to as ethical hackers, and for good reason – they need to infiltrate well-secured systems to pinpoint loopholes that black hat hackers can parasitize for nefarious purposes.

The Need for Pentesters Is Growing

When it comes to expertise required for effective pentesting, the bar is set so high that companies run into serious hurdles hiring qualified specialists for the job. The challenge stems from the fact that there is a big talent gap in cybersecurity these days. The demand propels significant financial rewards in this market niche. According to Cyberseek, the average salary of a mid-level pentester is $101,000.

To excel in unveiling security imperfections in IT environments, a pentester has to master the following skills:

Programming skills needed to infiltrate digital networks.
Expertise in cybersecurity and adjacent areas, including forensics and system analysis.
Having an idea of how real crooks piggyback the human factor to gain a foothold in IT systems.
Understanding the financial, reputational, and managerial impacts of a security breach.
Problem-solving and communication skills.
Ability to document the discovered vulnerabilities in a clear-cut way.
Keeping abreast of the latest security perils.

It’s also noteworthy that every instance of penetration testing should fit the context of a specific organization and the industry it represents.

Pentester’s Duties

Thinking like an attacker is a hugely important prerequisite for a successful penetration testing exercise. This provides visibility of the full spectrum of methods in a cybercriminal’s repertoire. Unsurprisingly, some of the best pentesters out there are former hackers who repurposed their skills to assist companies in safeguarding their systems.

If you want to build a career in this area, your work will include planning and carrying out simulated attacks, documenting your techniques along with findings, and in some cases facilitating patches and fine-tuning security protocols to fend off emerging cyber threats. The following list of responsibilities will give you the bigger picture:

Probing digital systems and applications for security flaws.
Coming up with new mechanisms to spot security holes.
Assessing the security of servers and other network gear to find areas that could use better physical protection.
Determining the techniques threat actors can leverage to exploit weak links in an organization’s security posture.
Analyzing, documenting, and discussing pentest results with the company’s IT personnel and senior executives.
Providing feedback regarding the efficiency of security enhancements that the customer has implemented.
Suggesting refinements of the existing security solutions, procedures, and policies.
Singling out areas where security awareness training of the personnel is necessary.

The Ins and Outs of a Penetration Tester’s Job

Ideally, before taking this route you need to hone your technical skills by working as a coder or a system administrator for some time. This will give you a deep understanding of how enterprise resource planning (ERP), customer relationship management (CRM), virtual private network (VPN), and other commonplace enterprise systems operate.

Also, keep in mind that this activity isn’t always fun. Be ready to tackle the adverse “byproducts” of pentesting, such as stress, fatigue, and occasional slip-ups. Self-organization is hugely important, because you will have to stick with three distinct stages of a pentest. First, you must scrutinize the architecture of the target system and evaluate its defenses. Then comes the hacking part. Finally, you need to thoroughly document and explain your findings to the customer, including non-technical management staff.

In most scenarios, pentesters spend many hours at their keyboard examining the organization’s IT infrastructure remotely. But sometimes, they visit the client’s premises and employees’ workplaces to learn additional details. This largely depends on the selected pentesting method relating to the scope of access to network infrastructure, such as black-box, gray-box, or white-box testing.

Pentesting vs Vulnerability Assessment vs Bug Bounties

Vulnerability assessment is geared toward identifying all security flaws in a system and prioritizing the patches based on their severity. This kind of service is very useful for companies whose executives understand that they have issues and need assistance in addressing them.

Contrary to this, pentesters are usually hired by customers who think they have matured in terms of security and want to make doubly sure that their defenses are strong enough and they comply with industry regulations. The report should explain how a specific area was compromised to achieve a predefined goal, such as accessing the customer database or changing a record in the staff management system.

Bug bounty programs resemble pentesting in a way, except that they involve any number of experts who look for weaknesses and errors in customers’ systems. Also, pentesters are paid hourly or get regular wages, whereas bug bounty hunters earn rewards based on the severity of vulnerabilities they found.

Certifications and Other Prerequisites for a Bright Pentesting Career

When deciding whom to hire for a pentest, many customers pay attention to industry certifications in addition to a candidate’s practical experience. Here is a list of the documents that are widely recognized across the board:

Certified Ethical Hacker (CEH)
Certified Expert Penetration Tester (CEPT)
Certified Mobile and Web Application Penetration Tester (CMWAPT)
Certified Penetration Tester (CPT)
GIAC Certified Penetration Tester (GPEN)
Offensive Security Certified Professional (OSCP)

Today’s trend toward democratizing the certification area is warmly received by wannabe pentesters who can get started on a career at zero cost. Some of the top free cyber security certifications from reputable organizations include:

Certified in Cybersecurity (by International Information Systems Security Certification Consortium)
Kali Linux Fundamentals (by Cybrary)
Networking Essentials (by Cisco)
Ethical Hacking Essentials (by EC-Council)
Risk Management (by Open University)
NSE 1: Network Security Associate 1 (by Fortinet)

Also, make sure you stay on top of the current pentesting tendencies. Watch security conferences like DEFCON and Black Hat, sign up for relevant training courses, and get the hang of popular penetration testing tools such as Metasploit, Nessus, and Nmap to continuously polish your skills.

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