Caroline Wong, the Chief Strategy Officer at Cobalt.io, is known for her practical information security knowledge that stems from her diverse experiences as a Cigital consultant, a semantic product manager, and day-to-day leadership roles at both eBay and Zynga. Caroline teaches cybersecurity courses on LinkedIn Learning, is a member of the Forbes Technology Council, and was named 2019’s Cyber Educator of the Year in the 6th annual Cyberjutsu Awards. She graduated from UC Berkeley with a BS in Electrical Engineering and Computer Science, holds a Certificate in Finance and Accounting from Stanford Graduate School of Business, and authored the well-known textbook, Security Metrics, A Beginner’s Guide. In today’s episode, we have a personal and candid conversation with Caroline about the influence of her father in her decision to study engineering and her approach as a woman in the tech sector. She not only shares key leadership insights but also talks about how she shifted from relying on unhealthy coping mechanisms to a philosophy focused on meeting uncertainties and challenges with the perspective that it can be figured out once you get there.