Penetration testing is something that we've all been through and understand. We have a certain level we expect from our penetration tests and testers but as we begin to look at what penetration tests symbolize and give us, they are fundamentally flawed and lacking. The Information Security field in general is relatively new in lifespan and as a maturity model we have to grow. Penetration tests should focus on understanding the business, understanding the organization, and impacting what hurts the organization the most, their bottom line. This talk will focus on strategically attacking an organization and how a penetration test should really be done and what it needs to be used for. We'll of course be showing some exploitation techniques and the latest and greatest sexy hacker moves.