How to Become an Elite Hacker: A Pen Tester’s Career Roadmap episode artwork

EPISODE · Sep 11, 2026 · 54 MIN

How to Become an Elite Hacker: A Pen Tester’s Career Roadmap

from Tech Jobber Podcast · host Chris Schwenk

Want to become a penetration tester or start a career in ethical hacking? In this video, we break down what it actually takes to get into penetration testing and cybersecurity, from learning the technical fundamentals to getting certifications, passing technical interviews, building hands-on experience, and landing your first cybersecurity job. Cybersecurity expert Phil Wiley explains the difference between ethical hacking and penetration testing, what a penetration tester actually does, which technical skills matter, how cybersecurity certifications can help, and why hands-on ability can be more valuable than simply collecting certifications. 📌 In this video:How to become a penetration testerHow to get started in cybersecurityEthical hacking vs penetration testingRed team vs blue team vs purple teamWhat penetration testers actually doA day in the life of a pen testerCybersecurity skills you need to learnBest certifications for penetration testingHands-on cybersecurity certificationsPenetration testing interview questionsHow technical cybersecurity interviews workBug bounties and getting real-world experienceHow to get your first penetration testing jobCybersecurity career advice for beginnersHow to build a cybersecurity personal brandUsing LinkedIn to get cybersecurity jobsHow content creation can help your cybersecurity careerNetworking for cybersecurity jobsHack The Box, CTFs and hands-on practice The video also explains why beginners shouldn't jump straight into penetration testing without understanding networking, operating systems, servers and security fundamentals. It also covers technical assessments, cybersecurity certifications, bug bounty experience, personal branding, LinkedIn, networking and how demonstrating your actual skills can help you stand out when applying for cybersecurity jobs. If you're interested in ethical hacking, penetration testing, offensive security or building a cybersecurity career, this interview gives you practical advice on where to start and how to progress. 🔗 Connect with Phil Wylie🌐 Website / Show: https://phillipwylieshow.com💼 LinkedIn: https://www.linkedin.com/in/phillipwylie/📸 Instagram: https://www.instagram.com/phillipwylie/▶️ YouTube: https://www.youtube.com/channel/UCeZgoXbccmkcf9viz974MEA 📖 The Pentester BlueprintWant to learn more about building a career in penetration testing?The Pentester Blueprint: Starting a Career as an Ethical Hacker by Phil Wylie.https://www.amazon.com/dp/1119684307?lv=shuf&channelId=500&plpRedirect=mhFallback Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Episode metadata supplied by the publisher feed · Published Sep 11, 2026

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How to Become an Elite Hacker: A Pen Tester’s Career Roadmap

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