Joanna Wiggum is the founder and agency principal of Countervail, a cybersecurity and licensed investigative agency providing fractional CISO services, cybercrime investigations, and adversary-informed training shaped by Fortune 100 security leadership, red-team expertise, enterprise incident response, and the operational discipline of military aviation.

She brings more than two decades of experience across Air Force mission operations, enterprise cybersecurity leadership, Big Tech incident response, red-team operations, and cybercrime prevention. Joanna began her career as an Air Force Interface Control Technician supporting operations during Operation Enduring Freedom and Operation Iraqi Freedom. After three years of enlisted service, she was awarded a command-nominated scholarship to commission as an officer, and later earned her wings as a B-52 Weapons Systems Officer, operating in high-consequence environments where timing, trust, and decision discipline directly affected mission outcomes.

Her cybersecurity career includes building and delivering Starbucks’ red team, serving as Director of Cybersecurity over Application Security and Vulnerability Management, leading Oracle Cloud red-team operations, building Oracle Cloud’s Trust and Safety program, and leading Microsoft security incident response across Azure Cloud and AI environments.

Joanna holds a bachelor’s degree in International Security Studies and a master’s degree in Human Relations, combining formal study in security, strategy, and human behavior with operational experience across military and enterprise cybersecurity environments. Her current work focuses on how adversaries exploit trust, authority, pressure, and human decision-making in ways traditional security controls often miss.