Fairly or unfairly, penetration testing has attracted a lot of interest from infosec wannabes. As a result, there seem to be a lot of presentations catering to aspiring penetration testers that turn out to be a 50 minute sign that says “Learn Metasploit.” This presentation is a fast-paced, often hilarious, 30-45 minute (tailorable for room for questions) romp that explores practical career points from a penetration tester. Rather than a dictionary of tools you should learn, or an encyclopedia of certifications, this presentation explores the breadth of infosec as a career discipline, the varieties of pentesting within that, and day today challenges within pentesting consulting and corporate security as a result of surveying dozens of pentest pros. The presentation will explore traits of successful pentesters who attack these daily challenges and offer insight into penetration testing as a career for those who think they may be interested. Heather Pilkington is a penetration testing consultant for Accuvant, and formerly a member of Spiderlabs. She has inflicted her fast-paced and humor driven speaking style on audiences at local conferences and bsides events for several years. With more than ten years of experience in information security (including more than 5 years in threat and vulnerability management), she has a breadth of disciplines from which to draw.