Staff Engineer, Offensive Security

Twilio is a company shaping the future of communications by providing innovative solutions to businesses and developers worldwide. The Staff Engineer in Offensive Security acts as a Technical Lead, focusing on penetration testing and vulnerability management while also designing complex attack simulations to assess systemic risks.

Responsibilities:

• Full-Stack Penetration Testing: Perform manual and automated testing of web applications, APIs, and mobile apps (iOS/Android)
• Internal/External Network Audits: Conduct network and cloud level assessments with various tooling
• Vulnerability Validation: Triage and validate reports from automated scanners or bug bounty hunters to eliminate false positives and escalate true positives
• AI/LLM Probing: Perform initial prompt injection and jailbreak tests on AI prototypes, services, and applications using established checklists (OWASP Top 10 for LLMs)
• Technical Reporting: Draft high-quality reports that detail the "path to compromise" with clear, reproducible steps for developers
• Tool Maintenance: Manage and update the team's testing infrastructure (e.g., Burp Suite, and basic C2 listeners)
• Remediation Support: Provide direct technical guidance to engineering teams on how to patch vulnerabilities like XSS, SQLi, and IDOR
• Adversary Emulation: Design and lead multi-week Red Team operations that mimic specific threat actors (APTs) to test the SIRT detection capabilities
• Custom Exploit Development: Build custom payloads, droppers, and obfuscated scripts to bypass EDR/AV and maintain stealth
• 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
• Cloud & Infrastructure Attacks: Execute sophisticated attacks against AWS/Azure/K8s, focusing on IAM misconfigurations and container escapes
• Purple Teaming: Collaborate with SIRT and Detection Engineering to tune SIEM alerts based on the techniques used during an engagement
• Strategic Bug Bounty Management: Oversee the organization's bug bounty program, identifying trends in submissions to suggest broad architectural security changes

Requirements:

• Experience: 7-10 years in offensive security, penetration testing, a high-volume bug bounty background, AppSec, or vulnerability exploitation, and track record of finding high/critical vulnerabilities in complex environments using pentesting commercial or custom tools
• Concepts: Expert Knowledge and solid understanding of the MITRE ATT&CK matrix and the OWASP Top 10 for web applications and top 10 for LLMs, post exploitation (lateral movement, persistence, data exfiltration) and Adversarial ML
• Tooling: Proficient in OffSec popular tools like Burp Suite professional, Nmap, Metasploit, Wireshark etc... and AI security tools such as LangChain, TensorFlow for adversarial testing or, as well as use of C2 frameworks (Cobalt Strike, Sliver, Havoc) or similar tools
• Scripting and Coding: Ability to write functional scripts in Python or Bash to automate repetitive testing tasks and proficiency in coding and scripting like Python, C++, and scripting for creating custom offensive exploits that avoids signature-based detection
• Certifications: Possession of advanced industry certifications such as OSCP, OSEP, OSWE, GXPN or similar training in OffSec tracks is highly desirable
• Telecom expertise is preferred
• Excellent written and verbal communication skills
• Ability to influence and build effective working relationships with all levels of the organization
• Proficiency in multiple languages applicable to the region