Penetration Tester

Bank of Montreal•Virtual, TX

7d•Remote

About The Position

Join a team where your work goes beyond checklists protecting critical Network and Cloud environments with real business and regulatory impact. This role offers high-impact, meaningful work where you will directly influence the security of Network/Cloud environments and AI solutions. You will focus on deep, manual penetration testing (Network, Cloud, and AI with human in the loop), not automated, scanner-driven assessments. Work in complex, enterprise-scale environments that expose you to advanced architectures and evolving threats, providing accelerated technical growth. You will engage across the full lifecycle: scoping → testing → reporting → remediation, with visibility and influence throughout. Use advanced testing tools to enhance testing depth and efficiency, experiencing fewer, higher-quality engagements versus consulting-style, high-volume work. Ongoing training is expensed.

Requirements

Bachelor’s degree in Information Security, Information Technology, Information Systems Management, Computer Science, Engineering or related field(s) or equivalent demonstrated work experience.
Strong written and verbal skills with the ability to present complex technical observations to a non-technical audience.
Good time management skills; the ability to commit and adhere to time-sensitive deliverables.
Ability to work remotely, with or without others, take direction, and be a self-starter that takes initiative.
Min of 3+ years experience with Manual Penetration Testing of Networks, Cloud Environments.
Strong exposure for testing in the following areas: Active Directory Environments and associated vulnerabilities and exploitation techniques.
Strong exposure for testing in Cloud Environments and associated vulnerabilities in commonly used features utilized in large multi-tenant and hybrid enterprise environments.
Strong proficiency with security testing tools and penetration testing Linux distributions such as Kali.
Deep practical knowledge of applying the Mitre Attack framework.
Ability to identify and exploit vulnerabilities in Active Directory environments and Cloud workflows as well as multi-step attack paths.
Network and Cloud architecture understanding.
Proficiency in at least one scripting language.
Ability in documenting reproducible steps for technical accurate findings.
Typically between 4 - 7 years of relevant experience and a post-secondary degree in Information Security, Computer Science, Engineering, and/or Information Systems or a related field of study or an equivalent combination of education and experience.
Understanding of industry standards and frameworks e.g. NIST Cyber Security Framework (CSF), ISO 27001 and 27002, Payment Card Industry (PCI) Data Security Standard (DSS), etc. - In-depth.
Experience in information security concepts and methodology.
Knowledge of business analysis, project delivery practices and standards across the project lifecycle - In-depth.
Knowledge of information security processes, procedures and controls - In-depth.
Understanding of and problem solving ability for information security issues within their business group - Working.
Understanding of information security risk and regulatory requirements - Working.
Deep knowledge and technical proficiency gained through extensive education and business experience.
Verbal & written communication skills - In-depth.
Collaboration & team skills - In-depth.
Analytical and problem solving skills - In-depth.
Influence skills - In-depth.
Data driven decision making - In-depth.

Nice To Haves

Preference for candidates who have at least one certification in a related field, with strong preference for Information security certifications from a well-recognized institution (e.g. OSCP, OSEP, HackTheBox Cloud security testing certificates, etc).
Experience with security testing of agentic AI solution is a plus.
Experience with security testing of CI/CD pipelines is a plus.
Preference for candidates who have at least one certification in a related field, with strong preference for Information security certifications from a well-recognized institution (e.g. (ISC)2, ISACA, SANS).

Responsibilities

Assists in delivery of security testing projects according to a structured process, to include writing test reports.
Assists with the execution of highly technical/analytical security assessments of Active Directory environments, network infrastructure, cloud environments, and AI technologies, including manual, custom and industry known attack methods using a risk-based intelligence-led methodology.
Identifies potential misuse scenarios.
Advises on secure development practices.
Provides technical leadership to business areas as a Security Testing subject matter expert.
Assists with efforts on the execution of security testing operations to include pre-engagement (scoping), engagement (testing) and post-engagement activities (reporting).
Works with leadership to mature security testing team capabilities including reporting and remediation guidance in alignment with local and global regulatory requirements.
Identifies security gaps and deficiencies by conducting risk assessments; able to recommend corrective action of identified vulnerabilities and weaknesses.
Assists with the execution of planning, testing, tracking, and advises on necessary risk acceptance for identified security risks.
Assists security testing activities aimed at exploiting vulnerabilities in order to enhance the security of BMO network, cloud, and AI technologies.
Works with management and peers to foster the development of less experienced Security Testing Consultants.
Performs hands-on penetration testing for BMO overall and businesses/groups.
Liaises with stakeholders to understand problems and opportunities and enables BMO to meet its goals by understanding business vision, objectives and KPIs.
Provides technical consultation to business areas as a Security Testing subject matter expert.
Assists with efforts on the execution of security testing operations to include pre-engagement (scoping), engagement (testing) and post-engagement activities).
Understands and can explain to others the core processes, risks and mitigation techniques for identified security gaps.
Develops and champions information security best practices, including staying abreast of industry information security and business trends through participation in professional associations.
Facilitates discussions and follows a disciplined approach to plan, elicit, analyse, document, communicate and manage initiatives and issues with stakeholders by applying a variety of elicitation techniques to probe, challenge and understand associated risks.
Provides information security consulting services for BMO overall and businesses/groups.
Leads the development of information security strategy by understanding business processes, policies, information and information systems.
Builds exceptional relationships with internal and external stakeholders.
Ensures that requirements and solutions align to a real business need, are approved by all relevant stakeholders, and meets essential information security standards.
Provides thought leadership, promotes new processes and methodologies and emerging technologies, with the flexibility to align to the unique requirements of the business/group and deliverables.
Acts as a trusted advisor to assigned business/group.
Assists in the development of strategic plans.
Understands and can explain to others the core processes, risks and mitigation techniques for designated areas.
Supports the execution of strategic initiatives in collaboration with internal and external stakeholders.
Helps determine business priorities and best sequence for execution of business/group strategy.
Breaks down strategic problems, and analyses data and information to provide insights and recommendations.
Acts as the day to day contact for vendors; supports the implementation, maintenance, and sustainment of vendor solutions.
Understands the strategy, plans, activities and needs of all stakeholders and translates those business needs into solutions and makes recommendations.
Provides advice, counsel and support on information security matters and recommends solutions to assigned business/group leaders on principles, frameworks, programs, approaches, trends, legislation and regulatory requirements including interpretation of policy and identification and management of risk.
Builds credibility and influences/negotiates effectively to drive business performance through development and delivery of information security solutions.
Tracks metrics and milestones, providing recommendations for resolution and escalating as appropriate when issues arise.
Promotes process improvements and methodologies; keeps emerging information security issues and trends in mind and ensures standards are followed.
Creates professional presentations and deliver them in a meaningful concise way.
Assesses information security impact to a project’s benefits and risks when scope changes.
Gathers, examines and interprets data and information to extract meaningful insights, answer business questions and provide actionable recommendations.
Assists with continuous improvement activities and root cause analysis with the goal of strengthening information security capabilities.
Ensures consistent, high quality practices/work and the achievement of business results in alignment with business/group strategies and with productivity goals.
Provides specialized consulting, analytical and technical support.
Exercises judgment to identify, diagnose, and solve problems within given rules.
Works independently and regularly handles non-routine situations.
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.