AI Penetration tester

Bank of Montreal•Virtual, FL

1d•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. 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.

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.
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.
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.
Gathers requirements and documents these requirements for use in various audits, reports, & projects.
Identifies opportunities to strengthen the capability of the information security organization at BMO, such as: sharing expertise to promote technical development, mentoring employees, building communities of practice and networks across information security and technology.
Works with internal stakeholders to validate their requirements via techniques such as reviews and walkthroughs.
Facilitates discussions and follows a structured approach to plan, elicit, analyze, document, communicate and manage requirements.
Analyzes data and information to provide insights and recommendations.
Collects, organizes, analyzes and disseminates significant amounts of information with attention to detail and accuracy.
Develops and implements data collection systems and other strategies that optimize statistical efficiency and data quality.
Identifies, analyzes, and interprets trends or patterns in complex data sets.
Provides analytical support and insights.
Filters and "cleans" data, and reviews reports and key performance indicators to locate and correct data issues.
Performs documentation writing and maintenance of new and existing processes, procedures and requirements.
Recommends approaches to streamline and integrate information security processes in the organization to improve overall efficiency.
Remains alert to new information security technologies and threats that present risk to the enterprise and determines the best approach to mitigate these risks.
Stays abreast of industry trends/risks related to information security, technology and business trends / risks through participation in professional associations, practice communities & individual learning.
Ensures consistent, high quality practices/work and the achievement of business results in alignment with business/group strategies and with productivity goals.
Operates at a group/enterprise-wide level and serves as a specialist resource to senior leaders and stakeholders.
Applies expertise and thinks creatively to address unique or ambiguous situations and to find solutions to problems that can be complex and non-routine.
Implements changes in response to shifting trends.
Broader work or accountabilities may be assigned as needed.
Take measured risks while protecting the bank by applying our Risk Management Framework in the execution of your role, in line with our Risk Culture and within our approved Risk Appetite, making sound and risk informed decisions that align to business strategy, protect assets, and adhere to applicable policy documents (Frameworks, Policies, Standards, Procedures and Supporting documents), laws and regulations.