A Roadmap for a Career in Cybersecurity

Written by
Rebecca Smith

Sep 28, 2021

Sep 28, 2021 • by Rebecca Smith

Few cybersecurity areas 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 forestall real-world attacks. A pentester worth their salt should have outstanding tech skills, be a social engineering guru, and have enough confidence to outsmart seasoned IT professionals working for large corporations.

The Need for Pentesters is Growing

The bitter truth is that there is a big talent gap in cybersecurity these days. The demand for such professionals propels the financial rewards in this niche. According to Payscale, the average salary of a mid-level pentester is $103,000. The bar is set high in terms of qualifications, too. To excel in this job, a pentester has to master the following skills:

  • Fluency in programming.
  • Expertise in cybersecurity and adjacent areas, including forensics and system analysis.
  • Having an idea of how crooks piggyback on the human factor to gain a foothold in IT systems.
  • Understanding the financial, reputational, and managerial impacts of a virus attack or a security breach.
  • Problem-solving and communication skills.
  • Ability to document the discovered vulnerabilities in a clear-cut way.

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

A Rundown of a Pentester’s Duties

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 the findings, and in some cases facilitating patches and fine-tuning security protocols. 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 require better physical protection.
  • Determining the techniques threat actors can leverage to exploit weak links in the organization’s security posture.
  • Analyzing, documenting, and discussing pentest results with the company’s IT personnel and senior executives.
  • 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

First things first, 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 function.

Self-organization is also 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.

In most scenarios, pentesters spend many hours at their keyboard examining the organization’s IT infrastructure remotely. But sometimes, they have to visit the client’s premises and employees’ workplaces to learn additional details. 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.

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. 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 find.

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)

Also, make sure you stay on top of the current pentesting trends. Watch security conferences like DEF CON 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 refine your skills.