Adversarial AI, Offensive Security Analyst

Vanguard

Senior Offensive Security Analyst leading AI-augmented red team engagements. Harnessing AI and automation for enhanced security operations across various threats and vulnerabilities.

Posted 6/9/2026full-timeMalvern • North Carolina, Pennsylvania, Texas • 🇺🇸 United StatesMid-LevelSeniorWebsite

Tech Stack

Tools & technologies

Cyber SecurityPython

About the role

Key responsibilities & impact

Plan & Execute AI-Enhanced Attacks: Lead red team operations and penetration tests that incorporate LLM-driven techniques and agentic automation to simulate sophisticated adversaries at scale.
Maintain human-in-the-loop oversight to ensure safe, controlled execution.
Custom Tooling & Automation: Design or integrate custom offensive tools and scripts that use AI/ML (e.g. LLM APIs, automation frameworks) to accelerate vulnerability discovery, exploit development, and testing workflows.
For example, develop internal frameworks that interface LLMs with red team C2 platforms (like MythicMCP, SliverMCP) to enable autonomous or semi-autonomous operations.
Adversarial Simulation & Fraud Testing: Conduct adversarial exercises targeting both technical systems and fraud controls, using AI to emulate how attackers might abuse scale and automation.
Work with fraud risk teams to simulate large-scale abuse scenarios (bots, deepfakes, automated scams) using AI capabilities.
Collaboration & Purple Teaming: Partner closely with blue teams (SOC, Detection Engineering) and fraud prevention teams to share insights from AI-augmented tests.
Help validate and improve detection and response for AI-driven attack techniques through joint purple team exercises.
Reporting & Knowledge Sharing: Document attack scenarios, findings, and mitigations in clear reports. Present results and risk insights to both technical staff and executives, translating complex AI-augmented attack methods into actionable defense improvements.
Mentor colleagues in adopting AI-assisted tools and foster a culture of innovation in the team.

Requirements

What you’ll need

5–7+ years of hands-on experience in penetration testing, red teaming, or adversary simulation with a strong track record.
Deep understanding of network/web application security, exploitation techniques, and attacker TTPs (MITRE ATT&CK).
Proven experience leveraging AI/ML or automation in cybersecurity (e.g. using LLM APIs, scripting against AI services, building security chatbots or automation pipelines).
Ability to craft effective prompts and interpret LLM outputs.
Familiarity with integrating AI into tools or workflows (experience with frameworks like Model Context Protocol (MCP) servers is a strong plus).
Proficiency in Python or similar languages for developing custom tools, automation scripts, and integrating APIs.
Bachelor's degree in computer science, engineering, or equivalent experience.
Industry certifications such as OSCP, CRTE or similar are preferred, demonstrating advanced offensive skills.

Benefits

Comp & perks

Health insurance
Retirement plans
Paid time off
Flexible work arrangements
Professional development

ATS Keywords

✓ Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

penetration testingred teamingadversary simulationnetwork securityweb application securityexploitation techniquesAI/MLscriptingPythonprompt crafting

Soft Skills

collaborationmentoringcommunicationreportingknowledge sharinginnovation

Certifications

OSCPCRTE