Lead Penetration Tester

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The McKesson Pentest Team is seeking a Lead Penetration Testing Engineer to help scale McKessons 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 McKessons 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 McKessons offensive security capabilities.

• Lead the design implementation and scaling of McKessons 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.

• Lead the design implementation and scaling of McKessons 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.

• 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.

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 McKessons 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 pleaseclick here.

Our Base Pay Range for this position

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