Staff Engineer, Offensive Security at Twilio

This role is designed for a seasoned offensive security expert with 7–10 years of experience who wants to operate at the intersection of traditional penetration testing and cutting-edge AI security. As a technical lead, you won't just be running scanners; you will be designing complex attack chains, conducting Red Team operations, and building automated frameworks to probe LLMs for vulnerabilities like prompt injection and data leakage. Twilio offers a fully remote environment in Ireland with a culture that prioritizes professional autonomy and "remote-first" collaboration. This position provides a unique opportunity to shape the security posture of a global communications giant, moving beyond standard AppSec to tackle sophisticated cloud infrastructure attacks (AWS/Azure/K8s) and adversary emulation. **You might be a good fit if you...** * Have a deep background in manual penetration testing and hold advanced certifications like OSCP, OSEP, or GXPN. * Are proficient in Python or C++ and can write custom exploits that bypass EDR/AV detection. * Feel comfortable leading multi-week Red Team engagements and collaborating with SIRT on "Purple Teaming" to improve detection. * Are curious about AI security and have experience with tools like Burp Suite, Cobalt Strike, or adversarial ML frameworks.