AI Penetration tester

About this role

Application Deadline:

10/29/2026

Address: VIRTUAL09 - HomeRes - FL

Job Family Group: Technology

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.

KEY 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.

CORE Skills : • 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.

Provides analysis and reporting services in support of businesses/groups and BMO overall. Builds relationships and liaises with stakeholders to understand problems and opportunities and recommends solutions to enable the organization to meet its goals. Analyzes data and creates documents and plans in service of informing, advising, or updating internal stakeholders. Ensures that requirements map to a real business need, are approved by all relevant stakeholders, and meet essential quality standards. Participates or conducts user acceptance testing to ensure that changes made are in alignment with business requirements. Provides great customer service in support of the information security processes, applications and infrastructure. • Provides strategic input into business decisions as a trusted advisor. • Acts as a subject matter expert on relevant regulations and policies. • Provides specialized analytical support to senior management. • May network with industry contacts to gain competitive insights and best practices. • Understands and can explain to others the core processes, risks and mitigation techniques for designated areas. • Anticipates and reduces complexity for others. • Develops innovative approaches to resolve problems and significant issues. • Provides input to the strategic direction of the group. • Acts as the prime subject matter expert for internal/external stakeholders. • Ensures alignment between stakeholders. • Defines business requirements for analytics and reporting to ensure data insights inform business decision making. • Analyzes trends to proactively prevent problems. • Presents and communicates at all levels within IT and across business units. • Prepares and delivers presentations for senior leaders. • Leads the preparation of end user reference materials and prepares end-user training materials. • Develops innovative approaches to resolve problems and significant issues. • Works with vendors to troubleshoot issues, as required. • Assesses the quality of reports submitted and provides related coaching and support. • Looks for coaching opportunities with other team members. • Troubleshoots information security issues within designated business group. •

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