Introduction Summary: In this episode of Cyber 909, host Den Jones introduces the podcast and welcomes guest Jake Bernardes, a seasoned multi-CISO and host of the Risking It All podcast. [00:20] Den highlights Jake's extensive experience in the cybersecurity field and his involvement in the CSO Society group. Guest Highlights: Background: Jake Bernardes is a seasoned multi-CISO and host of the Risking It All podcast. He has a diverse background, having worked in various regions including the UK, US, Far East, and Middle East. Key Contributions: Hosts the Risking It All podcast, focusing on people and leadership topics. [00:53] Currently the CISO at Anecdotes, a GRC automation platform. [14:04] Holds advisory and fractional CISO roles. [31:54] Extensive experience in pen testing, consulting, and working with startups. Known for his expertise in social engineering and cybersecurity strategy. Main Topics Covered: Jake's Background and Journey: Discussion on Jake's career path, including his early interest in computers, university studies in Chinese, and various roles in cybersecurity. [03:51] Role of Compliance in Cybersecurity: Debate on whether compliance equals security, with Jake emphasizing that they are different but both important. [25:40] Cyber Insurance: Jake's critical view on the effectiveness of cyber insurance and its role in the industry. [29:44] CISO's Role and Evolution: Conversation on the evolving role of CISOs, the importance of business acumen, and the need for CISOs to demonstrate value beyond technical expertise. [33:25] Strategic Security Management: Insights into how CISOs can align security strategies with business goals and the importance of being adaptable and creative in problem-solving. [33:25]