Lead Penetration Tester

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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.

Basic Requirements

• 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.

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

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