Explore the application of ChatOps to penetration testing in this conference talk from the Hack In The Box Security Conference. Learn how chatroom-driven DevOps concepts can be adapted for distributed penetration testing teams, utilizing chatbots like Hubot to execute custom scripts and plugins. Discover the tools used, including RocketChat, Hubot, Gitlab, and various pentesting tools, and gain insights from real-world experiences of implementing Pentesting ChatOps. Delve into topics such as routine scanning, spearphishing, and pentest gamification. The speaker, Melanie Rieback, CEO and Co-founder of Radically Open Security, shares her expertise in computer security, RFID security research, and cyber crime analysis, drawing from her diverse background in academia, industry, and entrepreneurship.