Explore a comprehensive conference talk that challenges conventional security practices and introduces the concept of "shifting left" in software development. Delve into the journey of adopting Security BSides Group (SBG) methodologies, examining both successes and challenges. Learn how to gather essential data, address knowledge gaps, and transform security teams from enforcers to enablers. Discover strategies for upskilling developers and testers, and understand the evolving role of penetration testing in modern security frameworks. Gain insights into implementing a holistic security approach, achieving unexpected wins, and ultimately improving the bottom line through proactive security measures.