**_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 interact with APIs, including automation and integration validation. + Demonstrated ability to create advanced scripts, tools, and automation using PowerShell, Python, or Bash. + Strong report‑writing skills with the ability to translate technical findings into business‑aligned risk and actionable remediation. + Leadership qualities to support technical development of team members. **Tooling Expectations (Hands‑On):** + Recon & Enumeration: Nmap, Masscan, Amass, Subfinder, Nuclei, Nikto, whatweb, dnsrecon, enum4linux‑ng + Web & API Testing: OWASP ZAP, sqlmap, ffuf/gobuster, testssl.sh, JWT tooling, Burp Suite + Exploit & Post‑Exploitation: Metasploit, Impacket, BloodHound, Responder, Kerbrute, CrackMapExec/NetExec, smbclient, LDAP tooling + Passwords & Traffic: Wireshark/tshark, John the Ripper, Hashcat, Hydra **Responsibilities:** + Conduct authenticated and unauthenticated web application penetration tests on internal and third‑party applications; identify vulnerabilities aligned to OWASP Top 10/ASVS, demonstrate exploitability, and validate fixes. + Perform internal and external network penetration tests, including attack path discovery, privilege escalation, lateral movement, segmentation validation, and internet‑facing exposure reviews. + Execute targeted security testing in additional domains such as APIs, mobile applications (as applicable), cloud configuration/exposure validation, and wireless assessments. + Build and maintain repeatable testing playbooks covering reconnaissance, exploitation, post‑exploitation, evidence collection, and remediation validation. + Produce clear deliverables including executive summaries, technical reports, reproducible steps, risk ratings, and remediation guidance; brief engineers, stakeholders, and security leadership. + Partner with application and infrastructure teams to remediate findings, conduct retesting, confirm closure, and improve secure SDLC practices. + Support purple‑team activities by collaborating with detection and response teams to strengthen logging, alerting, and detection logic. + Develop and maintain testing tools, scripts, and automations in Python, PowerShell, and Bash. + Mentor junior team members to expand technical knowledge and hands‑on capabilities. • Work with third‑party testers to define scopes, oversee execution and reporting, and assign ownership of findings. **One or more of the following certifications:** + Highly Preferred: OSCP, OSWE, OSEP, OSWP, or OSEE + GIAC: GPEN, GWAPT, GXPN, or GWEB + eCPPT or PNPT + Bonus: CISSP, cloud security certifications (AWS/Azure), or other relevant credentials. **Core Competencies:** + Analysis: Identify issues, compare data, and draw defensible conclusions. + Communication: Clearly convey technical details and risk to engineers, finding owners, and leadership. + Judgment & Decision Making: Recommend appropriate actions based on available facts and constraints. + Technical Knowledge: Stay current on offensive security techniques, defenses, and industry trends. + Relationship Building: Collaborate effectively with partners to achieve security objectives. + Client Focus: Support internal teams as customers while managing firm‑wide risk. + Leadership: Share knowledge and provide mentorship through training and guidance.