If you have ever thought of becoming a pen tester, then this article is for you. You'll learn fundamentally everything about becoming a pen tester; how they work, what they do on a typical day, where they work, how much they make, what training is needed, the dangers involved in this job, the chances of being replaced by robots (including artificial intelligence) and finally at what age do pen testers retire at. I call the pen testers "the shadow guardians" because you don't necessarily know they exist, but they are here and supporting the society. One thing is certain, without them, it would be chaos.
Being a pen tester means getting paid to hack a company's systems before an actual criminal do. You can either work remotely or on site. A big part of being a pen tester is writing reports documenting how you got in and how to fix it (or what you are planning to do next). It can be particularly stressful when time pressures you, but the rhythm installs itself.
Simple, pen testers, from its longer form penetration testers, are cybersecurity professionals who use a handful of hacking tools to patch security holes. In other words, they are the hackers of the good side. Let me develop more, the companies hire them to voluntarily hack their apps, networks, websites, pretty much anything the company has. By voluntarily hacking, pen testers can find security weaknesses and fix them before a real hacker finds the vulnerability and cause damage to the company.
Pen testers working for a company begin the day of work by reviewing their schedule and objectives for the day. After that, they start to hack the organisation within ethical boundaries of course. First, the scanning part; know the environment to hack inside and out. While the scans are still running, the pen testers analyse the information in real time and are already planning what to do next. If there are any vulnerabilities, it is imperative to report them to the team. To conclude the day, pen testers write a report on what they saw, what they did, and what they plan to do the next days.
Pen testers work in government, financial services, healthcare and, of course, IT enterprise. In Canada, this includes federal agencies, the RCMP (or GRC in French) and DND (or MDN in French). Pen testers can work from their house for a company, or even as freelancers. They can also work hybrid, meaning half the time they work on-site.
To become a pen tester, you need to learn the fundamentals which are networking, operating systems and basic scripting. A degree helps a lot but isn't required. To gain experience, practice on platforms like Hackthebox or Tryhackme, enter competitions and earn certifications such as CEH, Security+ or OSCP. Alternatively, to gain experience, many people start to work in an IT role not necessarily related to cybersecurity. They do that just to add something to the resume. After that, they apply for junior pen tester positions.
Now, let's talk money. In 2026, an entry-level pen tester earns between $65,000 and $86,000 before taxes (0 to 2 years of experience). A mid-level pen-tester earns between $95,000 and $115,000 (3 to 5 years of experience). Finally, a senior-level pen tester earns between $130,000 and $175,000 (6+ years of experience). The average salary is around $102,000. Keep in mind that those salaries are before taxes.
If you're a student who has a normal path through university and get his degree, I'm sorry to announce it, but it won't be enough. A pen tester absolutely needs experience through internships and certifications. Common ones are Comptia PenTest+, CEH and Security+ to start things off. A more advanced one is OSCP, which employers really prefer the most. Pen testers also keep learning through labs, competitions and learn even more like cloud and AI security. In other words, they never stop learning.
The dangers of being a pen tester are mostly psychological, not physical. Tight client deadlines and the pressure of results that directly affects a company's security can lead to burnout, which is a known circumstance in the field. There are also legal risks such as working outside the limits given by the company, accidentally accessing an unauthorized system, or leaking sensitive data.
For now, the chances are pretty low, but the market is constantly changing. AI and automated tools already handle routine work like scanning and basic exploitation, which hurts entry-level roles, and indirectly, people who are motivated to start working in this field. However, AI still struggles with complex flaws and creative attack chains. In a Hackerone survey, only 12% of researchers believed AI would replace them. As of now...
It's not a job with a fixed retirement age, so it depends on each individual and each employer.
In conclusion, pen testing is a demanding but rewarding career in which professionals legally hack systems of organizations to prevent a real criminal exploiting a vulnerability. It requires experience and certifications more than a degree. Plus, it pays well in Canada, from $65,000 to over $170,000. Now, due to multiple attacks on cyber infrastructures from unregulated AIs, in the future, will AI itself secure our systems against his "comrades" (AI attackers)? The enemy may be closer than we think...
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