No Password Required: From Heavy Metal to the Front Lines of Cyber Innovation
August 25, 2025
Jon Schipp, the “Ric Flair of Cybersecurity,” is the senior director of inorganic growth strategy at Rapid7. Jon mixes cyber technical mastery, business acumen, and stage presence to identity mergers and partnerships for his company’s growing cybersecurity platform. He shares his story with hosts Jack Clabby of Carlton Fields and Kayley Melton, executive director of operations at the Cognitive Security Institute, starting with his early days in the Midwestern heavy metal scene.
He opens up about couch surfing his way to hacker conferences as a teenager, the role of music in shaping his professional edge, and why knowledge — not money — has always been his North Star. With a background in security engineering, incident response, and software development, Jon explains that curiosity has been the through line in his journey and how his own startup experience prepared him to evaluate new technologies and teams. He also tells the story of a pitch so good it left the room stunned.
In the lifestyle polygraph segment, Jon reveals his dream guitar (an elusive LTD H-300 last seen in Evansville, Indiana) and gives the audience a crash course in heavy metal history. Plus, you’ll hear the tale of a pushup challenge that became an unforgettable part of a job interview — and meet Kayley’s cat, Little Baby, making her YouTube debut
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