Jon Schipp — From Heavy Metal to the Front Lines of Cyber Innovation Jon Schipp, the “Ric Flair of Cybersecurity,” is the Senior Director of Inorganic Growth Strategy at Rapid7. Schipp 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, P.A., 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, Schipp 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 push-up challenge that became an unforgettable part of a job interview—and meet Kayley’s cat, Little Baby, making her YouTube debut. Follow Jon on LinkedIn: https://www.linkedin.com/in/jonschipp/
Summary
In this episode of No Password Required, host Jack Clabby and co-host Kayleigh Melton engage in a lively conversation with John Shipp, a product strategist at Rapid7. They explore John's unique journey from a metalhead to a cybersecurity expert, discussing the importance of passion in career development, the intricacies of product management, and the significance of customer insights in shaping cybersecurity solutions. John shares his early experiences in hacking, the influence of music on his life, and the value of building strong teams and company culture. The episode concludes with a fun segment called the Lifestyle Polygraph, where John answers quirky questions about his ideal cyber team and his dream day with Ric Flair.
Chapters
00:00 Introduction to Cybersecurity and Personal Journeys
02:49 The Role of Passion in Career Development
05:21 Navigating Product Management and Market Strategy
08:23 The Evolution of Cybersecurity Skills
11:37 The Importance of Customer Insights in Product Development
14:35 Early Experiences in Hacking and Cybersecurity
17:24 The Influence of Music on Personal and Professional Life
20:19 Building Teams and Company Culture
23:10 Startup Life and Risk Management
26:08 Lifestyle Polygraph: Fun Questions and Insights
29:13 Final Thoughts and Connections