In a digital age marked by rapid technological advancements and increased global connectivity, ensuring cybersecurity for large corporations can often seem daunting. Today, I am joined by Doug Shepherd, Senior Director of Offensive Security and Global Insider Risk for Jones Lang LaSalle (JLL). This leading, billion-dollar real-estate services company spans 80 countries. JLL's challenges are multifaceted: ensuring the safety of a decentralized workforce, navigating the complex terrains of diverse privacy laws and regulations across continents, and maintaining real-time visibility into an impressive 100,000 endpoints. During our insightful chat, we delved deep into the previous security issues faced by JLL. The intricacies of having endpoint checks just every 75 days, coinciding with password changes, posed significant risks. Doug sheds light on the dynamics of managing security across different jurisdictions, emphasizing the importance of local expertise and overarching global strategies. Together, we explore the prevalent cyber threats that JLL and other organizations of its stature grapple with. Doug shares the transformative impact of real-time endpoint monitoring on JLL's cybersecurity posture, highlighting its role in enhancing incident response capabilities. The broader industry has its challenges.  Doug and I discuss the relentless pace of the cybersecurity sector, the balancing act between data privacy and augmented security measures, and the critical symbiosis between security and business. The episode also touches on innovative training programs and technologies, such as Immersive Labs and CASB, that are ushering in a new era of cybersecurity preparedness. Wrapping up, Doug, with his rich background as a former 'spook' and red team leader, offers a nuanced perspective on the pressing need to find the middle ground between rigorous data collection and upholding privacy. Join us in this riveting episode as we journey through the cyber labyrinths of a global giant and uncover the strategies, challenges, and solutions that shape the future of organizational security.