Offensive Security Engineering Lead

Remote - US

Full Time USD 140K to 201K
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The Who, What, Why and Where

Twilio is growing rapidly and seeking an exceptional Offensive Security Engineering Senior Manager to help find the biggest threats to Twilio’s security. The person in this role will conduct offensive engagements both externally outside the corporate network and internally within various enterprise environments with the goal of testing/validating security controls, identifying security gaps, and testing/validating blue team detection and response.

This individual will also work strategically with our Risk teams to help prove out and tell the story around our top risks to the business.


Twilio is looking for an exceptional penetration tester who lives the Twilio Magic and also has: 

  • 5+  years of experience in Security
  • You’re able to people manage and grow a red team function
  • You're empathetic, patient, and love to help your fellow teams grow
  • You're empathetic, patient, and love to help your teammates grow
  • You’re an expert in managing and executing all steps of the engagement lifecycle
  • You have strong communication and collaboration skills. You should be able to partner with and articulate identified vulnerabilities and risks to non-technical stakeholders
  • You have a strong knowledge of and applied experience in Docker, Kubernetes, Distributed Systems, Microservice Architectures, and AWS
  • You have extensive experience building custom tooling and automation
  • OSCP or other similar certifications preferred
  • Bachelor’s degree in information security, information technology, computer science, computer engineering, or equivalent experience
  • Bonus: You’re knowledgeable of GCP and non-cloud environment 


As the Senior Manager Offensive Security & Assessments Engineer, you will live the Twilio Magic values: 

  • DON’T SETTLE: Every engagement is an opportunity for Twilio’s security and engineering programs to grow, we should take advantage of each of these opportunities. 
  • BE AN OWNER: We’re not just breaking, we’re also building and improving by working across security and engineering teams to help drive control improvements.
  • WRITE IT DOWN: It’s critical that we write down what we did, how we did, why it’s important, and how we could build a better Twilio from these engagements.
  • BE BOLD: TTPs and capabilities shouldn’t be static, but constantly evolving. We would love to see you bring new types of engagements to Twilio.
  • EMPOWER OTHERS: The best security programs do not operate in silos, we share knowledge and experience with other members of the security and engineering teams



At Twilio, maintaining customer trust is our top priority. Keeping that in mind, so we do the right thing when things go wrong requires extraordinary discipline and technical leadership. And that’s where you fit in.

Twilio is a company that is empowering the world’s developers with modern communication in order to build better applications. Twilio is truly unique; we are a company committed to your growth, your learning, your development, and your entire employee experience.  We only win when our employees succeed and we're dedicated to helping you develop your strengths. We invest in weeks dedicated to tackling hard problems and creating your own ideas. We have a cultural foundation built on diversity, inclusion, and innovation and we want you and your ideas to thrive at Twilio.


Around the world, Twilio offers benefits and perks to support the physical, financial, and emotional well being of you and your loved ones. No matter where you are based, you will experience a company that believes in small teams for maximum impact; seeks well-rounded talent to ensure a full perspective on our customers’ experience,  understands that this is a marathon, not a sprint; that continuously and purposefully builds an inclusive culture that empowers everyone to do their best work and be the best version of themselves.

About Us

Millions of developers around the world have used Twilio to unlock the magic of communications to improve any human experience. Twilio has democratized communications channels like voice, text, chat, video and email by virtualizing the world’s communications infrastructure through APIs that are simple enough for any developer to use, yet robust enough to power the world’s most demanding applications. By making communications a part of every software developer’s toolkit, Twilio is enabling innovators across every industry — from emerging leaders to the world’s largest organizations — to reinvent how companies engage with their customers.


In accordance with applicable law, the following represents Twilio's reasonable estimate of the range of possible compensation for this role if hired in Colorado. Please note that this information is provided for those hired in Colorado only, and this role is open to candidates outside of Colorado as well. 



Denver/Boulder Metro:

$160,896 - $201,120

Rest of Colorado:

$140,874 - $175,980


Additionally, this role is eligible to participate in Twilio's equity plan.


An overview of Twilio’s benefits offered is listed below:


Twilio is committed to delivering a comprehensive benefits program that provides support needed for you and your loved ones. It’s likely that you don’t think about benefits every day; however, they are an important component of your total compensation, and we want you to understand the options available to you so that you can make the most of your benefit dollars.  At the time of this posting, this role is eligible to participate in the following benefits, which Twilio reserves the right to modify at any time for any reason in accordance with applicable law:


Healthcare Insurance and Leave

  • Prescription Drug
  • Dental
  • Vision 
  • Flexible Spending and Health Savings Accounts
  • Leave programs for all of life’s moments: maternity, parental/bonding, as well medical leave to care for yourself or a loved one


Financial Benefits

  • Short and Long Term Disability Insurance
  • Life and Accidental Death & Dismemberment Insurance
  • 401(k) Retirement Savings Plan with a match


Reimbursement Programs & Stipends

  • $65 per month work-from-home stipend
  • Up to $50 per month for wellness expenses and activities
  • Up to $30 per month to use towards books/eBooks


Job region(s): Remote/Anywhere North America
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