Join host G Mark Hardy in this episode of CISO Tradecraft as he welcomes Olivia Rose, an experienced CISO and founder of the Rose CISO Group. Olivia discusses her journey in cybersecurity from her start in marketing to becoming a VCISO. They delve into key topics including the transition from CISO to VCISO, strategies for managing time and stress, the importance of understanding board dynamics, and practical advice on mentoring new entrants in the cybersecurity field. Olivia also shares her insights on maintaining business alignment, handling insurance as a contractor, and building a personal brand in the cybersecurity community. Olivia Rose: https://www.linkedin.com/in/oliviarosecybersecurity/ Transcripts: https://docs.google.com/document/d/1S42BepIh1QQHVWsdhhgx6x99U188q5eL Chapters 00:00 Introduction and Guest Welcome 01:14 Olivia Rose's Career Journey 06:42 Challenges in Cybersecurity Careers 15:47 Communicating with the Board 22:57 Navigating Compliance and Legal Challenges 24:10 Building Strategic Relationships 25:46 Aligning Security with Business Goals 35:05 The Importance of Reputation and Branding