Lead Penetration Testing Engineer - Raymond James Financial, Inc. - St. Petersburg, FL

Job Description Summary

The financial services industry sits squarely in the crosshairs of today’s most capable threat actors from nation states to highly organized criminal enterprises. Our internal cybersecurity organization operates where theory meets reality, continuously pressure testing defenses, exposing risk before attackers do, and raising the bar for enterprise security.

As a Lead Penetration Testing Engineer, you will lead and execute penetration testing engagements across web and mobile applications, internal and external networks, and other in-scope environments, taking ownership from planning through execution, technical debriefs with stakeholders and verifying remediation success. You will coordinate penetration tests, including red team and purple team exercises, working side by side with elite third-party testing partners as well as internal threat hunting, detection engineering, infrastructure, and security teams to turn findings into measurable security improvements.

This is a hands-on role for an offensive security professional who thrives in complex environments, enjoys breaking assumptions, and wants their work to directly shape enterprise wide defense strategy.

Job Description

This position follows our hybrid workstyle policy: Expected to be in a Raymond James office location a minimum of 10-12 days a month.

Please note: This role is not eligible for Work Visa sponsorship, either currently or in the future.

Experience & Skills:

7+ years of offensive security experience as a red team operator and penetration tester across web applications, corporate networks, and infrastructure.

Strong understanding of networking fundamentals and protocols (TCP/IP, DNS, HTTP/S, TLS, SMTP, SMB, Kerberos, LDAP, etc.).

Deep familiarity with Windows and Linux, including Active Directory, authentication flows, endpoint posture, and common misconfigurations.

Proven ability to test and in