Senior Manager of Offensive Security at Twilio

This is a high-impact leadership role for a veteran security professional with over 10 years of experience, specifically in offensive security and red teaming. The ideal candidate is a "technical leader" who hasn't lost their edge; you should be as comfortable discussing business risk with the Board as you are overseeing exploit development or specialized AI threat modeling. Twilio offers a competitive salary (up to $276k in some regions) plus equity and bonuses in a remote-first culture. This role is particularly interesting because it bridges traditional penetration testing with cutting-edge **Adversarial AI testing**, challenging you to secure LLMs and GenAI features against prompt injection and jailbreaking. **You might be a good fit if you...** * Have a deep background in red teaming environments across AWS, GCP, and Kubernetes. * Hold advanced certifications like OSCP, OSEP, or GXPN and can script in Python, Go, or C++. * Are experienced in "Purple Teaming," collaborating with defense teams to turn attack findings into better detection logic. * Live in a permitted US state (Note: Candidates in CA, CT, NJ, NY, PA, and WA are **not** eligible for hire per the "Location" section, though the compensation section lists several of these states—candidates should clarify residency eligibility early).