
Episode #3
Listening is the Super Power in the World of AI
In this episode of 2 Cyber Chicks, we’re joined by Jessica Weiland of Bishop Fox — part relationship builder, part problem solver, and part professional cat herder — who spends her days helping security teams tackle challenges, reduce risk, and move their programs forward. Whether she’s coordinating offensive security testing, planning strategic initiatives, or translating security-speak into business outcomes, Jessica works to make security easier to navigate and a lot less painful. In this conversation she gets practical about cutting through the AI hype and meeting both technical teams and business leaders exactly where they are — empathy and listening first. In this conversation, we dive into: • How to separate real AI risk from AI hype when you’re actually talking to a client • Explaining AI risk so it lands with technical teams and business leaders alike • Where AI fits into offensive security testing and red teaming • The misconception about AI and cybersecurity she wishes more people understood — and how to stay innovative while leading human-first This episode is a must-listen for security leaders, practitioners, and anyone who wants AI security to be less about hype and more about people, clarity, and outcomes that actually move the program forward. Guest Information: Jessica Weiland | Account Executive, Bishop Fox LinkedIn: https://www.linkedin.com/in/jessicaweiland/ ========================= Connect with 2 Cyber Chicks: LinkedIn: 2 Cyber Chicks Podcast Email us: 2CyberChicks@gmail.com Jax Scott, Founder, @TheZaraAI - Jax on LinkedIn: https://linkedin.com/in/iamjax - YouTube: Outpost Gray - Twitter/X: @outpostgray - Website: iamjax.me Erika McDuffie, Managing Principal, Coalfire Systems - Erika on LinkedIn: https://www.linkedin.com/in/erika-mcduffie-767394bb #2cyberchicks ========================= Learn more about our Season Sponsor @ThreatLocker Stop ransomware without the hassle. Allow what you need and block the rest with ThreatLocker Zero Trust Platform — simple to deploy, simple to manage. Learn more at https://threatlocker.com/2cyberchicks . ========================= All the ways to connect with @SimplyCyber https://SimplyCyber.io/Socials

