{"id":2832106,"url":"https://alion.io/job/mckesson-lead-penetration-tester","title":"Lead Penetration Tester","company":{"id":4393,"name":"McKesson","domain":"mckesson.com","url":"https://alion.io/company/mckesson","size_band":"5000+","is_staffing_agency":false,"employer_type":"direct","is_intermediary":false,"listed_via":null,"ats_vendor":"Workday","truth_index":{"grade":"B","score":80,"open_postings":33,"ghost_share":0,"stale_share":1,"repost_share":0,"time_to_fill_p50_days":12,"computed_at":"2026-10-24T06:02:35Z"}},"role":"Security","role_family":"Security","seniority":"lead","employment_type":"full_time","work_mode":"hybrid","remote_scope":null,"remote_scope_basis":null,"remote_working_hours":null,"hiring_geo_confidence":"structured","locations":["Mississauga, Canada"],"countries":["CA"],"hiring_countries":[],"hiring_countries_total":0,"salary":null,"salary_estimate":{"min_usd":77000,"max_usd":148000,"period":"year","method":"role_seniority_country_remote_cell","sample_n":16},"experience_years_min":null,"visa_sponsorship":false,"relocation_package":false,"has_equity":false,"technologies":[{"name":"Human-in-the-Loop","optional":false},{"name":"LLM Guardrails","optional":false},{"name":"CI/CD","optional":true},{"name":"Gmail","optional":true},{"name":"LLM","optional":true},{"name":"OWASP Top 10","optional":true},{"name":"Threat Modeling","optional":true}],"status":"live","first_seen_at":"2026-10-13T00:00:00Z","employer_posted_date":"2026-10-13","last_verified_at":"2026-10-23T07:59:57Z","board_verified":true,"closed_at":null,"days_open":12,"trust":{"level":"ok","repost_count":null,"flags":[],"days_open":12},"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.\nWhat 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.\nAbout the Role\nThe 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.\nThe 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.\nThis 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.\nWhat You'll Do\nLead the design, implementation, and scaling of McKesson’s Continuous Adversarial Testing program across large application portfolios.\nDevelop the CART operating model, including service definition, governance, intake, application prioritization, onboarding, testing cadence, validation, reporting, escalation, and remediation workflows.\nEstablish roles and responsibilities, decision authorities, guardrails, and controls for the safe use of autonomous and AI-assisted offensive security technologies.\nDefine application eligibility, readiness, and prioritization criteria based on business criticality, exposure, data sensitivity, architecture, authentication requirements, and regulatory obligations.\nDevelop repeatable onboarding processes covering application context, test accounts, authentication, authorization roles, test data, rate limits, WAF coordination, exclusions, maintenance windows, and emergency stop procedures.\nDefine testing standards and methodologies for web applications, APIs, cloud-native applications, and modern application architectures.\nEstablish human-in-the-loop processes for reviewing, reproducing, validating, prioritizing, and communicating findings generated by autonomous testing platforms.\nLead 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.\nDefine quality standards for evidence, reproducibility, severity, exploitability, business impact, false-positive disposition, and finding acceptance.\nDesign integrations between CART platforms and vulnerability management, engineering, reporting, and remediation workflows.\nEstablish 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.\nBuild mechanisms for measuring false-positive rates, duplicate findings, testing completeness, platform utilization, and actionable vulnerability yield.\nEvaluate emerging autonomous security testing capabilities and recommend changes to CART strategy, tooling, and service delivery.\nCreate program documentation, playbooks, runbooks, technical standards, training materials, and stakeholder communications.\nProvide technical leadership, mentoring, and strategic guidance while influencing enterprise security roadmaps, offensive security strategy, and architecture decisions.\nBasic Requirements\nLead the design, implementation, and scaling of McKesson's Continuous Adversarial Testing program across large application portfolios.\nDevelop the CART operating model, including service definition, governance, intake, application prioritization, onboarding, testing cadence, validation, reporting, escalation, and remediation workflows.\nEstablish roles and responsibilities, decision authorities, guardrails, and controls for the safe use of autonomous and AI-assisted offensive security technologies.\nDefine application eligibility, readiness, and prioritization criteria based on business criticality, exposure, data sensitivity, architecture, authentication requirements, and regulatory obligations.\nDevelop repeatable onboarding processes covering application context, test accounts, authentication, authorization roles, test data, rate limits, WAF coordination, exclusions, maintenance windows, and emergency stop procedures.\nDefine testing standards and methodologies for web applications, APIs, cloud-native applications, and modern application architectures.\nEstablish human-in-the-loop processes for reviewing, reproducing, validating, prioritizing, and communicating findings generated by autonomous testing platforms.\nLead 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.\nDefine quality standards for evidence, reproducibility, severity, exploitability, business impact, false-positive disposition, and finding acceptance.\nDesign integrations between CART platforms and vulnerability management, engineering, reporting, and remediation workflows.\nEstablish 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.\nBuild mechanisms for measuring false-positive rates, duplicate findings, testing completeness, platform utilization, and actionable vulnerability yield.\nEvaluate emerging autonomous security testing capabilities and recommend changes to CART strategy, tooling, and service delivery.\nCreate program documentation, playbooks, runbooks, technical standards, training materials, and stakeholder communications.\nProvide technical leadership, mentoring, and strategic guidance while influencing enterprise security roadmaps, offensive security strategy, and architecture decisions.\nPreferred Skills/Experience\nExperience implementing, operating, or scaling continuous security testing, attack simulation, breach and attack simulation, or automated offensive security capabilities.\nExperience establishing governance, onboarding processes, service-level objectives, success metrics, reporting, and operational workflows for security programs.\nExperience evaluating, validating, and triaging findings from automated or AI-assisted security testing platforms.\nExperience evaluating security technologies and managing relationships with security vendors and service providers.\nExperience assessing AI-enabled applications, agent-based systems, LLM integrations, or AI security risks.\nFamiliarity with DevSecOps, CI/CD security controls, and secure software development practices.\nKnowledge of OWASP Top 10, API Security Top 10, threat modeling, and secure design principles.\nExperience supporting regulated industries such as healthcare, finance, or other highly regulated environments.\nRelevant certifications such as OSCP, OSWE, OSWA, OSAI, HTB CWES, HTB CWEE, OSEP, GPEN, GWAPT or equivalent.\nKnowledge of offensive security automation frameworks and AI-assisted security testing capabilities.\nExperience developing proof-of-concept exploits and adversary emulation scenarios.\nTravel / Work Environment / Physical Requirements\nLimited travel may be required based on business needs.\nHybrid or remote work arrangements may be available in accordance with company policy.\nAbility to work at a computer and participate in virtual meetings for extended periods.\nMay be required to support cybersecurity incident response activities outside standard business hours when necessary.\nWe 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.\nOur Base Pay Range for this position\n$122,100 - $162,800McKesson has become aware of online recruiting-related scams in which individuals who are not affiliated with or authorized by McKesson are using McKesson’s (or affiliated entities, like CoverMyMeds or RxCrossroads) name in fraudulent emails, job postings or social media messages. In light of these scams, please bear the following in mind:\nMcKesson Talent Advisors will never solicit money or credit card information in connection with a McKesson job application.\nMcKesson Talent Advisors do not communicate with candidates via online chatrooms or using email accounts such as Gmail or Hotmail. Note that McKesson does rely on a virtual assistant (Gia) for certain recruiting-related communications with candidates.\nMcKesson job postings are posted on our career site: careers.mckesson.com.\nMcKesson is an Equal Opportunity Employer\nMcKesson 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.\nMcKesson 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)  or (Canada) . Resumes or CVs submitted to this email box will not be accepted.\nJoin us at McKesson!","description_format":"text","description_chars":11188,"description_truncated":false,"requirements":{"experience_years_min":null,"management_years_min":null,"team_size_min":null,"manages_managers":false,"education":null,"security_clearance":false,"languages":[]},"benefits":["Equity"],"hiring_locations":[{"name":"Canada","iso":"CA","kind":"country"}],"hiring_excludes":[],"relocation_offered":false,"industries":["Penetration Testing","Health Care","Pharmaceutical Distribution","Medical Equipment Distribution"],"lifecycle":[{"event":"open","at":"2026-10-19T03:39:23Z"}],"visa":[],"liveness":{"score":42,"band":"fade","label":"Fading","p_open":1,"p_active":0.554,"p_room":0.75,"age_days":11,"expected_fill_days":12,"reasons":["conf:22","stale_co","velocity","win:late","comp:brand"],"computed_at":"2026-10-24T06:02:35Z"},"pay":null,"html_url":"https://alion.io/job/mckesson-lead-penetration-tester","json_url":"https://alion.io/job/mckesson-lead-penetration-tester.json","meta":{"generated_at":"2026-10-25T04:10:13Z","cache_seconds":300,"methodology":"https://alion.io/methodology","terms":"https://alion.io/terms","contact":"https://alion.io/contact","api":"https://alion.io/developers","about":"Alion is a live layer of people, companies and AI agents: who they are, whether they are real and active right now, what they do and how to work with them, readable by people and by agents and paid per call.","catalog":"https://alion.io/catalog.json","usage":{"tier":"crawler_verified","counted_by":"address","units_charged":1,"used_today":5383,"day_limit":null,"remaining_today":null,"minute_limit":300,"resets_at":"2026-10-26T00:00:00Z"}},"offers":[{"id":"company.slices","title":"One company in depth, by slice","status":"live","price":{"credits":0.02,"usd":0.002,"plus_per_slice":{"credits":0.05,"usd":0.005}},"unit":"per company, plus each slice with data","note":"the employer in depth","call":{"mcp_tool":"get_company","arguments":{"id":4393},"rest":"https://alion.io/mcp/rest/get_company?id=4393"},"human":"https://alion.io/catalog?offer=company.slices&for=job%2Fmckesson-lead-penetration-tester"},{"id":"market.stats","title":"A market slice: pay, demand and time to fill","status":"live","price":{"credits":1,"usd":0.1},"unit":"per slice","note":"pay, demand and time to fill for this role and place","call":{"mcp_tool":"market_stats"},"human":"https://alion.io/catalog?offer=market.stats&for=job%2Fmckesson-lead-penetration-tester"},{"id":"job.search","title":"Open jobs by role, technology, place, pay and visa","status":"live","price":{"credits":0.02,"usd":0.002},"unit":"per posting in a list","note":"similar open postings","call":{"mcp_tool":"search_jobs"},"human":"https://alion.io/catalog?offer=job.search&for=job%2Fmckesson-lead-penetration-tester"},{"id":"company.verify","title":"Is this company real and active right now","status":"pilot","price":null,"unit":"per company","request":{"url":"https://alion.io/catalog/request","method":"POST","body":"{\"offer\": \"company.verify\", \"for\": \"job/mckesson-lead-penetration-tester\", \"note\": \"what you need it for\"}"},"human":"https://alion.io/catalog?offer=company.verify&for=job%2Fmckesson-lead-penetration-tester"}]}