Senior Manager of Offensive Security

Twilio

4h • Remote

About The Position

As the Senior Manager of Offensive Security and Red Teaming, you will lead an elite team of ethical hackers and security penetration testers dedicated to proactively uncovering and mitigating vulnerabilities across the enterprise and our products. You are a technical expert and a strategic leader. You will design and oversee sophisticated adversary emulation exercises that challenge our defenses, ensuring that our security team and overall security posture are prepared for real-world threats.

Requirements

• Experience: Minimum of 10+ years in cybersecurity, with at least 5 years specifically in offensive security roles and 2+ years in a leadership or management capacity.
• Technical Expertise: Deep knowledge of security frameworks like the MITRE ATT&CK framework, Cyber Kill Chain, and advanced exploitation techniques (e.g., AD, cloud, and applications attacks).
• Certifications: Possession of advanced industry certifications such as OSCP, OSEP, OSWE, GXPN or similar
• Infrastructure Knowledge: Proficient in attacking and defending diverse environments including AWS/Azure/GCP, Kubernetes, and hybrid-cloud architectures.
• Hands-on AI Testing: Proven experience in automating red teaming for GenAI and proficiency in using AI offensive tools like PyRIT, Prompfoo, Xbow or Counterfit to build and stage AI powered attacks
• Tooling Proficiency: Advanced experience with red team and penetration testing tools such as Cobalt Strike, Burp Suite Pro, Metasploit, BloodHound, and Sliver.
• Programming Skills: Strong ability to code or script in Python, PowerShell, Go, or C++ for exploit development and task automation.
• Analytical Thinking: Proven ability to connect individual vulnerabilities into complex attack chains that demonstrate significant business impact.
• Ethical Integrity: A flawless record of ethical conduct and the ability to handle extremely sensitive access and information with total discretion.

Nice To Haves

• Telecom expertise is preferred

Responsibilities

• Strategic Leadership: Develop and execute a multi-year roadmap for offensive security, including red teaming, penetration testing, bug bounty, and vulnerability research.
• Adversary Emulation: Design and lead full-scope red team engagements that simulate Advanced Persistent Threats (APTs) to test detection and response capabilities.
• Program Management: Oversee the end-to-end lifecycle of offensive engagements, from initial scoping and Rules of Engagement (RoE) to final reporting.
• Purple Teaming: Facilitate collaborative "Purple Team" exercises with Detection and Response (TDR) to improve detection logic and incident response playbooks.
• Executive Communication: Translate complex technical findings into actionable business risk assessments for C-suite executives and Board members.
• Team Mentorship: Recruit, retain, and develop a high-performing team of offensive security engineers, providing technical guidance and career coaching.
• Vulnerability Management Integration: Partner with vulnerability management, product, and engineering to ensure that findings from offensive tests are prioritized and remediated effectively.
• Tooling & Automation: Oversee the development of custom scripts, payloads, and C2 (Command and Control) frameworks to enhance the team’s stealth and efficiency.
• Adversarial AI Testing: Conduct specialized threat modeling for AI-native applications, focusing on the OWASP Top 10 for LLMs and MITRE ATLAS (Adversarial Threat Landscape for AI Systems).
• AI attacks and mitigations: Design and execute manual and automated Prompt Injection & Jailbreaking to bypass model guardrails, system prompts, and safety filters.
• Regulatory Compliance: Ensure all offensive activities align with legal, ethical, and regulatory standards (e.g., GDPR, SOC2, PCI-DSS).
• Threat Intelligence Integration: Incorporate current Cyber Threat Intelligence (CTI) into attack scenarios to ensure they reflect the latest real-world TTPs (Tactics, Techniques, and Procedures).
• Third-Party Oversight: Manage relationships and quality control for external security consultancy firms performing third-party penetration tests.
• Research & Development: Encourage and lead research into emerging technologies to identify future attack vectors.
• Cross-Functional Collaboration: Work closely with Product and Engineering teams to bake security into the Software Development Life Cycle (SDLC) through testing and assessments

Benefits

• Working at Twilio offers many benefits, including competitive pay, generous time off, ample parental and wellness leave, healthcare, a retirement savings program, and much more.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed