Information Security Specialist (US) - AI Penetration Tester

About the position The Information Security Specialist – AI Penetration Tester is responsible for conducting advanced offensive security testing across AI/ML systems, LLM integrations, GenAI platforms, and associated infrastructure. This role serves as a subject-matter expert in AI/LLM security, partnering with engineering, cyber, cloud, and architecture teams to identify vulnerabilities, improve controls, and ensure safe and compliant deployment of AI capabilities across the enterprise.

Responsibilities

• Conduct Penetration Tests: Design and execute comprehensive penetration tests targeting AI/ML models, LLM applications, model pipelines, retrieval systems, data agents, and AI-enabled business workflows.
• AI/LLM Vulnerability Analysis: Identify vulnerabilities such as jailbreaking, prompt injection, model extraction, adversarial ML attacks, data poisoning, RAG bypasses, and safety guardrail circumvention.
• Tooling & Automation: Evaluate and develop tooling (including internal utilities and open‑source frameworks) to automate and scale AI/LLM security testing.
• Assess Security Posture: Analyze training data governance, guardrail design, inference endpoints, system prompts, agent autonomy, model monitoring, and model‑ops pipelines.
• Risk Assessments: Perform security and safety risk analyses on new and existing AI/ML deployments, including cloud‑based services, APIs, model marketplaces, and third-party LLM integrations.
• Model Supply Chain Security: Assess AI supply chain risks, dependency integrity, and alignment with enterprise standards and regulatory obligations.
• Report Findings: Deliver clear, actionable findings to both technical and non‑technical stakeholders.
• Produce detailed reporting including: Executive summaries Technical proof‑of‑concepts Prioritized remediation recommendations
• Stakeholder Engagement: Collaborate with Engineering, Data Science, Cloud, Cyber Defense, Architecture, and Risk to remediate findings and improve AI security posture.
• Develop Best Practices: Contribute to organization-wide AI security standards, policies, control objectives, and hardening practices.
• Regulatory Compliance: Ensure AI penetration testing aligns with regulatory, privacy, model safety, and internal policy requirements.
• Continuous Learning: Maintain deep expertise in emerging AI threats, industry frameworks, evaluation methodologies, and global safety standards.
• Participate in AI/ML–related security incident investigations, providing subject-matter expertise on root cause analysis and exploitation methods.
• Support audit preparation and assist in drafting management responses, remediation plans, and risk treatment documentation.

Requirements

• 7+ years of relevant experience
• Expert knowledge of IT security and risk disciplines and practices
• Bachelor's degree preferred
• Information security certification / accreditation an asset

Nice-to-haves

• 5+ years in application security or penetration testing, with hands-on experience in AI/ML environments preferred.
• 7+ years of experience using penetration testing tools (Metasploit, Burp Suite, Nmap, Kali, etc.).
• Strong knowledge of AI/LLM vulnerabilities including OWASP Top 10 for LLMs, adversarial attacks, prompt injection, and model safety testing frameworks.
• Familiarity with scripting and automation (Python preferred), model interrogation techniques, and cloud-native AI services (Azure, AWS, GCP).
• Experience penetration testing AI/LLM platforms, cloud workloads, and PCI-scoped environments.
• Knowledge of security frameworks (NIST AI RMF, OWASP LLM/ML, ISO 42001, MITRE ATLAS).
• Relevant certifications: OSCP, CEH, GPEN, CISSP, or AI/ML security certifications.
• Experience supporting audits, compliance reviews, and incident response activities.

Benefits

• Total Rewards at TD includes base salary and variable compensation/incentive awards (e.g., eligibility for cash and/or equity incentive awards, generally through participation in an incentive plan) and several other key plans such as health and well-being benefits, savings and retirement programs, paid time off (including Vacation PTO, Flex PTO, and Holiday PTO), banking benefits and discounts, career development, and reward and recognition.

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