Lead Penetration Tester

McKesson; Mississauga; Hybrid; CAD 174,000 - 232,000; Full time

Job summary

McKesson seeks a Lead Penetration Testing Engineer to scale its CART program and strengthen its enterprise security posture. You will lead offensive security initiatives, focusing on AI-enabled testing, cloud and web app assessments, and vulnerability validation across large portfolios.

You will partner with engineering, product, cloud, and security teams to identify attack paths, validate threats, and drive remediation while shaping the future direction of McKesson’s offensive security

Qualifications

• Experience implementing, operating, or scaling continuous security testing, attack simulation, breach and attack simulation, or automated offensive security capabilities.
• Experience establishing governance, onboarding processes, service‑level objectives, success metrics, reporting, and operational workflows for security programs.
• Experience evaluating, validating, and triaging findings from automated or AI‑assisted security testing platforms.
• Experience evaluating security technologies and managing relationships with security vendors and service providers.
• Experience assessing AI‑enabled applications, agent‑based systems, LLM integrations, or AI security risks.
• Familiarity with DevSecOps, CI/CD security controls, and secure software development practices.
• Knowledge of OWASP Top 10, API Security Top 10, threat modeling, and secure design principles.
• Experience supporting regulated industries such as healthcare, finance, or other highly regulated environments.
• Relevant certifications such as OSCP, OSWE, OSWA, OSAI, HTB CWES, HTB CWEE, OSEP, GPEN, GWAPT or equivalent.

Responsibilities

• Lead the design, implementation, and scaling of McKesson’s CART program across large application portfolios.
• Develop the CART operating model, including governance, onboarding, testing cadence, and remediation workflows.
• Establish guardrails and controls for autonomous and AI-assisted offensive security technologies.
• Define testing standards for web apps, APIs, cloud-native apps, and modern architectures.
• Lead continuous AI-assisted penetration tests, onboarding, orchestration, validation, and remediation coordination.
• Define quality standards for evidence, reproducibility, severity, and finding acceptance.
• Design integrations between CART platforms and vulnerability management, engineering, and reporting workflows.
• Provide technical leadership and strategic guidance to influence security roadmaps and architecture.

Skills

Continuous security testing

Attack simulation

Breach & attack simulation

AI‑assisted security testing

DevSecOps

Threat modeling

API security

OWASP Top 10

Security certifications

Job description

McKesson is an impact-driven, Fortune 10 company that touches virtually every aspect of healthcare. We are known for delivering insights, products, and services that make quality care more accessible and affordable. Here, we focus on the health, happiness, and well-being of you and those we serve – we care. What you do at McKesson matters. We foster a culture where you can grow, make an impact, and are empowered to bring new ideas. Together, we thrive as we shape the future of health for patients, our communities, and our people. If you want to be part of tomorrow’s health today, we want to hear from you.

About the Role

The McKesson Pentest Team is seeking a Lead Penetration Testing Engineer to help scale McKesson's Continuous Adversarial Testing (CART) program and strengthen the security posture of our enterprise application ecosystem. This role provides technical leadership for offensive security programs, focusing on AI-enabled security testing, web application penetration testing, cloud security assessments, vulnerability validation, and adversarial testing across large-scale application portfolios. The individual in this role will partner with engineering, product, cloud, and security teams to identify complex attack paths, validate threats, and drive remediation efforts that reduce business risk. The position will play a key role in operationalizing autonomous security testing capabilities, integrating CART outputs into security operations, and advancing McKesson's offensive security strategy. This role will also help shape the future direction of AI-assisted security testing, automation, and modern offensive security methodologies across the enterprise. This is a hands‑on technical leadership role for someone who can build a new security program while also performing advanced technical testing, validating AI‑generated findings, solving operational challenges, and guiding the long‑term direction of McKesson’s offensive security capabilities.

What You’ll Do

• Lead the design, implementation, and scaling of McKesson’s Continuous Adversarial Testing program across large application portfolios.
• Develop the CART operating model, including service definition, governance, intake, application prioritization, onboarding, testing cadence, validation, reporting, escalation, and remediation workflows.
• Establish roles and responsibilities, decision authorities, guardrails, and controls for the safe use of autonomous and AI-assisted offensive security technologies.
• Define application eligibility, readiness, and prioritization criteria based on business criticality, exposure, data sensitivity, architecture, authentication requirements, and regulatory obligations.
• Develop repeatable onboarding processes covering application context, test accounts, authentication, authorization roles, test data, rate limits, WAF coordination, exclusions, maintenance windows, and emergency stop procedures.
• Define testing standards and methodologies for web applications, APIs, cloud-native applications, and modern application architectures.
• Establish human‑in‑the‑loop processes for reviewing, reproducing, validating, prioritizing, and communicating findings generated by autonomous testing platforms.
• Lead the execution of continuous AI assisted penetration tests across high‑priority enterprise web applications, including application onboarding, test orchestration, execution oversight, findings validation, and remediation coordination.
• Define quality standards for evidence, reproducibility, severity, exploitability, business impact, false‑positive disposition, and finding acceptance.
• Design integrations between CART platforms and vulnerability management, engineering, reporting, and remediation workflows.
• Establish service metrics, key risk indicators, and executive reporting for application coverage, onboarding progress, testing frequency, finding quality, validated risk, remediation performance, retest outcomes, and program effectiveness.
• Build mechanisms for measuring false‑positive rates, duplicate findings, testing completeness, platform utilization, and actionable vulnerability yield.
• Evaluate emerging autonomous security testing capabilities and recommend changes to CART strategy, tooling, and service delivery.
• Create program documentation, playbooks, runbooks, technical standards, training materials, and stakeholder communications.
• Provide technical leadership, mentoring, and strategic guidance while influencing enterprise security roadmaps, offensive security strategy, and architecture decisions.

Preferred Skills/Experience

Experience implementing, operating, or scaling continuous security testing, attack simulation, breach and attack simulation, or automated offensive security capabilities.

Experience establishing governance, onboarding processes, service‑level objectives, success metrics, reporting, and operational workflows for security programs.

Experience evaluating, validating, and triaging findings from automated or AI‑assisted security testing platforms.

Experience evaluating security technologies and managing relationships with security vendors and service providers.

Experience assessing AI‑enabled applications, agent‑based systems, LLM integrations, or AI security risks.

Familiarity with DevSecOps, CI/CD security controls, and secure software development practices.

Knowledge of OWASP Top 10, API Security Top 10, threat modeling, and secure design principles.

Experience supporting regulated industries such as healthcare, finance, or other highly regulated environments.

Relevant certifications such as OSCP, OSWE, OSWA, OSAI, HTB CWES, HTB CWEE, OSEP, GPEN, GWAPT or equivalent.

Knowledge of offensive security automation frameworks and AI‑assisted security testing capabilities.

Experience developing proof‑of‑concept exploits and adversary emulation scenarios.

Travel / Work Environment / Physical Requirements

• Limited travel may be required based on business needs.
• Hybrid or remote work arrangements may be available in accordance with company policy.
• Ability to work at a computer and participate in virtual meetings for extended periods.
• May be required to support cybersecurity incident response activities outside standard business hours when necessary.

Compensation / Benefits

We are proud to offer a competitive compensation package at McKesson as part of our Total Rewards. This is determined by several factors, including performance, experience and skills, equity, regular job market evaluations, and geographical markets. The pay range shown below is aligned with McKesson's pay philosophy, and pay will always be compliant with any applicable regulations. In addition to base pay, other compensation, such as an annual bonus or long‑term incentive opportunities may be offered. For more information regarding benefits at McKesson, please click here.

Our Base Pay Range for this position $122,100 - $162,800

Equal Employment Opportunity

McKesson is an Equal Opportunity Employer McKesson provides equal employment opportunities to applicants and employees, without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, protected veteran status, disability, age, genetic information, or any other legally protected category.

For additional information on McKesson’s full Equal Employment Opportunity policies, visit our Equal Employment Opportunity page.

McKesson is committed to being an Equal Employment Opportunity Employer and offers opportunities to all job seekers including job seekers with disabilities.

If you need a reasonable accommodation to assist with your job search or application for employment, please contact us by sending an email to (United States) [e-mail] or (Canada) [e-mail].

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