AI Penetration Tester

BMO•Florida, MA

1d•$122,400 - $228,000•Remote

About The Position

Be among the first dedicated AI Penetration Testers at BMO and help shape how AI systems are secured, challenged, and trusted at enterprise scale. As part of BMO's Security Testing Team, you'll play a key role in building and advancing our AI Security Testing capability, assessing cutting-edge AI technologies, large language models (LLMs), AI agents, and GenAI solutions before they are deployed across the organization. In this highly visible role, you'll partner with cybersecurity leaders, engineers, architects, data scientists, and AI governance teams to identify emerging risks, develop innovative testing methodologies, and influence how AI security practices evolve across the enterprise. What Makes This Role Unique? Build something new: Help create and mature a first-of-its-kind AI Security Testing capability within BMO's Security Testing Team. Work with emerging technology: Evaluate LLMs, AI agents, GenAI platforms, and machine learning systems using cutting-edge adversarial testing techniques. Drive enterprise impact: Shape security outcomes for some of the bank's most strategic AI initiatives before they reach production. Create the future of AI testing: Design and develop new AI adversarial testing methodologies that become part of BMO's long-term security testing strategy. Expand your expertise: Lead security testing exercises, conduct AI threat research, and simulate emerging attack techniques targeting AI systems. Work alongside experts: Collaborate with leading security practitioners, AI engineers, architects, and governance teams to solve complex security challenges. Flexible remote work: Work remotely within EST or CST time zones. This role offers a rare opportunity to help define an emerging cybersecurity discipline while building expertise that is becoming increasingly critical across the industry. You'll have the opportunity to influence how AI is securely adopted at scale within one of North America's leading financial institutions. If you're passionate about offensive security, AI, and pushing the boundaries of what security testing can accomplish, this is a unique opportunity to help define the future of AI security at BMO. Work remotely in the USA within EST or CST time zones.

Requirements

Advanced penetration testing experience across web applications, APIs, and cloud environments.
Hands-on experience assessing AI/LLM technologies, AI agents, ML models, or GenAI applications.
Strong understanding of offensive security methodologies and adversarial attack techniques.
Experience with Python scripting and security tool development/automation.
Knowledge of OWASP Top 10, API Security Top 10, and emerging OWASP LLM Security risks.
Experience performing threat modeling and security assessments.
Strong understanding of authentication, authorization, identity, and cloud security concepts.
Ability to clearly document findings and remediation recommendations.
Typically 7+ years of relevant experience and a post-secondary degree in Information Security, Computer Science, Engineering, Information Systems, Business or in a related field of study or an equivalent combination of education and experience.
Multiple Information Security certifications from a well-recognized institution (e.g. (ISC)2, ISACA, SANS).
Expert in information security, technology, business requirements gathering and reporting in a financial services setting.
Data manipulation and analysis skills with the ability to collect, organize, analyze and disseminate significant amounts of information with attention to detail and accuracy - Expert.
Knowledge of Information Security processes, procedures and controls - Expert.
Understanding and problem solving ability of Information Security issues across the bank - Expert.
Understanding of industry standards and frameworks e.g. NIST Cyber Security Framework (CSF), ISO 27001 and 27002 - Expert.
Understanding of Information Security risk and regulatory requirements - In-depth.
Understanding of the scope of complexity that exists in the computing environment and the ways which security platforms impact that environment.
Seasoned professional with a combination of education, experience and industry knowledge.
Verbal & written communication skills - In-depth / Expert.
Analytical and problem solving skills - In-depth / Expert.
Influence skills - In-depth / Expert.
Collaboration & team skills; with a focus on cross-group collaboration - In-depth / Expert.
Able to manage ambiguity.
Data driven decision making - In-depth / Expert.

Responsibilities

Conduct security assessments of AI systems, LLMs, AI agents, and machine learning applications.
Perform adversarial testing including prompt injection, jailbreaks, model manipulation, and abuse-case testing.
Execute application, API, and cloud security testing supporting AI-enabled solutions.
Develop repeatable AI security testing methodologies, tools, and automation.
Partner with development and engineering teams to validate and remediate findings.
Produce technical reports and executive summaries communicating risks and recommendations.
Research emerging AI threats and attack techniques.
Support red team exercises involving AI-enabled attack scenarios.