Senior Manager of Offensive Security

Who we are

At Twilio, we’re shaping the future of communications, all from the comfort of our homes. We deliver innovative solutions to

hundreds of thousands of businesses

and empower millions of developers worldwide to craft personalized customer experiences.

Our dedication to

remote-first work

, 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.

We use Artificial Intelligence (AI) to help make our hiring process efficient. That said, every hiring decision is made by real Twilions!

.

See yourself at Twilio

Join the team as Twilio’s next Senior Manager of Offensive Security.

About The Job

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.

Responsibilities

In this role, you’ll:

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

Qualifications

Twilio values diverse experiences from all kinds of industries, and we encourage everyone who meets the required qualifications to apply. If your career is just starting or hasn't followed a traditional path, don't let that stop you from considering Twilio. We are always looking for people who will bring something new to the table!

*required

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.

Desired

Telecom expertise is preferred

Location

This Role Will Be Remote,

but is not eligible to be hired in CA, CT, NJ, NY, PA, WA.

Travel

We prioritize connection and opportunities to build relationships with our customers and each other. For this role, you may be required to travel occasionally to participate in project or team in-person meetings.

What We Offer

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. Offerings vary by location.

Compensation

*Please note the salary range information provided applies only to candidates residing in California, Colorado, Hawaii, Illinois, Maryland, Massachusetts, Minnesota, New Jersey, New York, Vermont, Washington D.C., and Washington State due to local requirements. Compensation for candidates in other locations will be discussed during the hiring process. Please note that hiring for this role is not restricted to the locations listed above.

The Estimated Pay Ranges For This Role Are As Follows

Based in Colorado, Hawaii, Illinois, Maryland, Massachusetts, Minnesota, Vermont or Washington D.C. : $188, 240 - 235,300.

Based in New York, New Jersey, Washington State, or California (outside of the San Francisco Bay area): $199,280 - 249,100.

Based in the San Francisco Bay area, California: $221,360 - $276,700.

This role may be eligible to participate in Twilio’s equity plan and corporate bonus plan. All roles are generally eligible for the following benefits: health care insurance, 401(k) retirement account, paid sick time, paid personal time off, paid parental leave.

The successful candidate’s starting salary will be determined based on permissible, non-discriminatory factors such as skills, experience, and geographic location.

Applications for this role are intended to be accepted until May 21st 2026,  but may change based on business needs.

Twilio thinks big. Do you?

We like to solve problems, take initiative, pitch in when needed, and are always up for trying new things. That's why we seek out colleagues who embody our values — something we call

Twilio Magic

. Additionally, we empower employees to build

positive change in their communities

by supporting their volunteering and donation efforts.

So, if you're ready to unleash your full potential, do your best work, and be the best version of yourself, apply now! If this role isn't what you're looking for,

please consider other open positions.

Twilio is proud to be an equal opportunity employer.

We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, consistent with applicable federal, state and local law. Qualified applicants with arrest or conviction records will be considered for employment in accordance with the Los Angeles County Fair Chance Ordinance for Employers and the California Fair Chance Act. Additionally, Twilio participates in the E-Verify program in certain locations, as required by law.