Coffee with CISOs featuring Jake Bernardes

In this episode of Coffee with CISOs, Katelyn Ruby sits down with Jake Bernardes, CISO at Anecdotes, to discuss his unconventional path into cybersecurity, the evolution of the modern CISO role, and why business leadership matters just as much as technical expertise in today's security landscape. Growing up in the Midlands of England, Jake's curiosity for understanding how things work led him from tinkering with computers and breaking video games to careers in consulting, penetration testing, IT leadership, and ultimately the CISO seat. Along the way, he developed a unique perspective on what separates strong security practitioners from strong business leaders. Together, they dive into topics including: ☕ How curiosity, hacking, and early exposure to technology shaped Jake's career ☕ Why financial literacy and business acumen are critical skills for today's CISOs ☕ The growing importance of executive leadership in cybersecurity ☕ Why AI is making security leaders more valuable... not less ☕ The role mentorship plays in accelerating career growth ☕ Building authentic relationships in an increasingly AI-driven world ☕ Raising resilient kids in the age of instant answers and automation ☕ What it takes to lead security teams through constant change and uncertainty One insight from Jake that stood out: "If a CISO is having to justify their role to the executive team, they're probably not acting like an executive." Throughout the conversation, Jake shares candid perspectives on leadership, resilience, mentorship, and the future of cybersecurity - offering practical advice for anyone looking to grow their impact inside and outside the security industry. If you enjoyed this episode, make sure to like, comment, and subscribe for more conversations with cybersecurity leaders shaping the future of the industry. Connect with Jake on LinkedIn:   / jakeleobernardes   Connect with Katelyn on LinkedIn:   / katelynruby   Stay connected and follow Lockstep on LinkedIn:   / lockstepvc   Learn more about Lockstep: https://www.lockstep.vc/