AI Penetration Tester

AI Penetration Tester

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.

Salary: $ - $

Pay Type:

Salaried

The above represents BMO Financial Group's pay range and type. Salaries will vary based on factors such as location, skills, experience, education, and qualifications for the role, and may include a commission structure. Salaries for part-time roles will be pro-rated based on number of hours regularly worked. For commission roles, the salary listed above represents BMO Financial Group's expected target for the first year in this position.

BMO Financial Group's total compensation package will vary based on the pay type of the position and may include performance-based incentives, discretionary bonuses, as well as other perks and rewards. BMO also offers health insurance, tuition reimbursement, accident and life insurance, and retirement savings plans.