Cynthia Wyre — Project Manager at Rapid7 and the Queen of Cyber Media

Episode 71 — Cynthia Wyre

Cynthia Wyre —Project Manager at Rapid7 and the Queen of Cyber Media

Cynthia Wyre is a Senior Strategic Engagement Project Manager at Rapid7, where she helps connect academic research and industry. Her path into cybersecurity innovation was untraditional, moving from healthcare and construction project management into vulnerability research and academic partnerships.

Cynthia reflects how she applied for a role she did not think she was qualified for, why professionals of all backgrounds belong in cyber, and how project management skills can open unexpected doors.

Jack Clabby of Carlton Fields, P.A., and K. Melton of the Cognitive Security Institute welcome Cynthia live from CyberBay 2026 in Tampa for a conversation about research, resilience, and relationship-building in cybersecurity. Cynthia explains Rapid7’s partnership with USF and Cyber Florida, including her efforts to support research around SOC analyst training and burnout, and the future of cyber education.

Throughout the conversation, Cynthia highlights the importance of community, mentorship, and helping people see that cybersecurity is not limited to one path or one type of person.

The episode wraps with the Lifestyle Polygraph, where Cynthia reveals how she would work a room full of strangers and how she won a costume contest moments before meeting rapper Young Gravy. She also earns a crown of her own, officially joining the No Password Required fantasy cybersecurity squad as Queen of the Podcast.

Follow Cynthia on LinkedIn: https://www.linkedin.com/in/cynthiawyre/

Presented by ThreatLocker
Follow ThreatLocker on LinkedIn: https://www.linkedin.com/company/threatlockerinc/posts/

Jon Schipp — From Heavy Metal to the Front Lines of Cyber Innovation

No Password Required Podcast Episode 63 — Jon Schipp

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/