Lead Analyst - Penetration Tester at Sysco

About the role

JOB DESCRIPTION Lead Analyst - Penetration Tester  The Big Picture  Sysco LABS is the Global In-House Center of Sysco Corporation (NYSE: SYY), the world’s largest foodservice company. Sysco ranks 56th in the Fortune 500 list and is the global leader in the trillion-dollar foodservice industry.    Sysco employs over 75,000 associates, has 337 smart distribution facilities worldwide and over 14,000 IoT-enabled trucks serving 730,000 customer locations. For fiscal year 2025 that ended June 29, 2025, the company generated sales of more than $81.4 billion. Sysco LABS Sri Lanka delivers the technology that powers Sysco’s end-to-end operations.    Sysco LABS’ enterprise technology is present in the end-to-end foodservice journey, enabling the sourcing of food products, merchandising, storage and warehouse operations, order placement and pricing algorithms, the delivery of food and supplies to Sysco’s global network and the in-restaurant dining experience of the end-customer.      The Opportunity  The Lead Analyst - Penetration Tester is a key role within Sysco’s Corporate Cybersecurity organization, responsible for leading offensive security testing across web applications, APIs, cloud platforms (Azure, AWS, GCP), and internal enterprise environments.  This is a senior individual contributor role suited for an experienced penetration tester who enjoys deep manual testing, uncovering complex attack paths, and partnering closely with Application Security, Cloud Security, Vulnerability Management, and Threat Hunting teams. The role includes planned evening or weekend testing for production environments, balanced with compensatory time off to maintain a sustainable work schedule.    Responsibilities:  Leading penetration testing of web and API applications, including JavaScript-heavy applications, WordPress, and Apache-backed services, using Veracode, Burp Suite, and advanced manual testing techniques  Conducting penetration testing and security assessments of cloud platforms (Azure, AWS, GCP) and internal infrastructure, including Active Directory, Azure AD, and identity systems  Assessing modern technologies such as AI/ML and LLM-backed components to identify misuse, data exposure, and abuse scenarios  Producing clear, structured penetration testing reports, communicate risk and remediation priorities, and supporting secure SDLC activities including design and code reviews  Manually retesting vulnerabilities to validate remediation and collaborating with threat hunters and detection engineers to validate detections based on real-world attack paths  Planning and scoping penetration testing engagements, including effort estimation and coordination of off-hours testing windows in alignment with change and maintenance schedules  Maintaining and improving penetration testing standards, tools, checklists, and playbooks across application, cloud, identity, and AI testing domains  Providing technical mentoring and guidance to junior and mid-level penetration testers    Requirements:  A Bachelor’s Degree in Cybersecurity, Computer Science, or a related field  5+ years of hands-on penetration testing or offensive security experience, including leading complex engagements  Strong expertise in web and API penetration testing, including authentication/authorization flaws, business logic issues, IDOR, SSRF, and injection vulnerabilities  Experience performing cloud security assessments across Azure, AWS, and GCP, identifying misconfigurations and privilege escalation paths  Hands-on experience assessing Active Directory and Azure AD environments using tools such as BloodHound  Must possess the ability to develop scripts, proof-of-concept exploits, and small tools using languages such as Python, PowerShell, or Bash  Strong written and verbal communication skills, with the ability to clearly present findings to technical and non-technical stakeholders    Preferred Qualifications:  A Master’s Degree in Cybersecurity, Computer Science, or a related field  7+ years of offensive security or penetration testing experience  Certifications such as OSCP, GPEN, GXPN, CEH, eCPPT, eWAPT, CPENT or equivalent  Familiarity with secure SDLC practices and contributing to security standards and playbooks  Experience testing AI/ML-enabled systems and identifying AI-specific abuse cases    Work Mode & Environment  Work Mode: Hybrid  Planned participation in evening or weekend testing windows, with compensatory weekdays off  Minimal travel required  Office-type remote work environment as part of a globally distributed security team    Benefits:    US dollar-linked compensation     Performance-based annual bonus     Performance rewards and recognition     Agile Benefits - special allowances for Health, Wellness & Academic purposes     Paid birthday leave    Team engagement allowance     Comprehensive Health & Life Insurance Cover - extendable to parents and in-laws     Overseas travel opportunities and exposure to client environments     Hybrid work arrangement       Sysco LABS is an Equal Opportunity Employer.