Pentesting or ethical hacking as it is more commonly known has become a much sought-after job by people in IT, InfoSec, or those just trying to get into the industry. In this presentation Phillip Wylie shares the blueprint for becoming a pentester. The presentation combines Phillip’s experience as a pentester and ethical hacking instructor to give attendees a guide to how to pursue a career as a pentester. Phillip shares what has worked for his students and people that he has mentored over his years as a pentester. This presentation covers the knowledge and skills needed to become a pentester as well as the steps to achieve them.


  1. Defining pentesting

    Discuss what a pentester is and a pentest their role in security. Discuss the different types of pentests including network, wireless, application, IoT and other hardware types as well as pentest specializations.

    Why become a pentester? -

    Discuss the benefits and outlook of pentesting career opportunities. Discuss other jobs where pentesting and hacking skills are useful.

  2. The Blueprint to Becoming a Pentester:

  • Foundation -
    Discuss the foundational perquisite knowledge needed to become a pentester. Discuss the IT basic skills such as operating systems, networking and security needed to be a pentester.

  • Hacking skills
    Discuss developing hacking skills and the hacker mindset.

  • Education options
    Discuss learning options such as college classes, security training providers and self-study.

  • Education resources
    Discuss education resources including; books, videos, conferences and community.

  • Certifications and degrees
    Discuss credentials useful for gaining employment as a pentester including; degrees and certificates.

  • Getting Experience – Discuss methods for developing hacking/pentesting skills such as labs (third party and home), CTFs, bug bounties,pro bono/volunteer work.

  • Developing a plan
    Discuss how to assess current skillset and knowledge to find a starting place and the perform a gap analysis to develop a learning plan. Discuss goal setting and educational milestones to track progress.

  • Getting employed as a pentester
    Discuss how to find a job as a pentester through networking, social media and community evolvement.

About Champion:

Phillip Wylie is a Principal InfoSec Engineer on the Assessment Services Penetration Testing Team at U.S. Bank. Phillip is an Adjunct Instructor at Richland College teaching Ethical Hacking and System Defense. Phillip is a Bugcrowd Ambassador and the founder of The Pwn School Project. Phillip has over 21 years of experience in InfoSec and IT and has performed pentests on networks, wireless networks, applications including thick client, web application and mobile. Phillip has a passion for sharing, mentoring and educating. This passion was his motivation to start teaching and founding The Pwn School Project, a free monthly educational meetup with a focus on hacking. Phillip holds the following certifications; CISSP, NSA-IAM, OSCP, GWAPT.


Phillip Wylie


Starts at Saturday April 13 2019, 07:30 PM. The sessions runs for about 2 hours.