<div class="content-intro">Who we are  At Twilio, we’re shaping the future of communications, all from the comfort of our homes. We deliver innovative solutions to<a class="c-link" href="https://customers.twilio.com/" target="_blank" data-stringify-link="https://customers.twilio.com/" data-sk="tooltip_parent"> hundreds of thousands of businesses </a>and empower millions of developers worldwide to craft personalized customer experiences. Our dedication to <a class="c-link" href="https://www.twilio.com/en-us/blog/open-work" target="_blank" data-stringify-link="https://www.twilio.com/en-us/blog/open-work" data-sk="tooltip_parent">remote-first work</a>, and strong culture of connection and global inclusion means that no matter your location, you’re part of a vibrant team with diverse experiences making a global impact each day. As we continue to revolutionize how the world interacts, we’re acquiring new skills and experiences that make work feel truly rewarding. Your career at Twilio is in your hands. A quick heads-up about hiring and how we work : We use Artificial Intelligence (AI) to help make our hiring process efficient. That said, every hiring decision is made by real Twilions!  Also, while we are a remote-first company, you may be asked to report in person on an ad-hoc basis for team gatherings, functional off-sites or customer meetings. </div>See yourself at Twilio Join the team as Twilio’s next Staff Offensive Security Engineer. About the job The Staff Engineer acts as a Technical Lead. You don t just find bugs; you design complex attack chains that demonstrate systemic risk. You spend as much time writing custom code and researching new bypasses as you do executing tests. Responsibilities In this role, you’ll: <ul> <li>Full-Stack Penetration Testing: Perform manual and automated testing of web applications, APIs, and mobile apps (iOS/Android).</li> <li>Internal/External Network Audits: Conduct network and cloud level assessments with various tooling</li> <li>Vulnerability Validation: Triage and validate reports from automated scanners or bug bounty hunters to eliminate false positives and escalate true positives</li> <li>AI/LLM Probing: Perform initial prompt injection and jailbreak tests on AI prototypes, services, and applications using established checklists (OWASP Top 10 for LLMs).</li> <li>Technical Reporting: Draft high-quality reports that detail the "path to compromise" with clear, reproducible steps for developers.</li> <li>Tool Maintenance: Manage and update the team s testing infrastructure (e.g., Burp Suite, and basic C2 listeners).</li> <li>Remediation Support: Provide direct technical guidance to engineering teams on how to patch vulnerabilities like XSS, SQLi, and IDOR.</li> <li>Adversary Emulation: Design and lead multi-week Red Team operations that mimic specific threat actors (APTs) to test the SIRT detection capabilities.</li> <li>Custom Exploit Development: Build custom payloads, droppers, and obfuscated scripts to bypass EDR/AV and maintain stealth.</li> <li>AI Red Teaming Architecture: Build automated testing frameworks for AI systems (e.g., using PyRIT, Promptfoo, or Garak) to test for models related to sensitive data leakage.</li> <li>Cloud & Infrastructure Attacks: Execute sophisticated attacks against AWS/Azure/K8s, focusing on IAM misconfigurations and container escapes.</li> <li>Purple Teaming: Collaborate with SIRT and Detection Engineering to tune SIEM alerts based on the

Staff Engineer - Offensive Security

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