Staff Adversarial Engineer

Okta, Inc.; Toronto; Remote; CAD 125,000 - 150,000; Full time

Job summary

Join a forward-thinking company as a Cybersecurity Operator, where you'll play a crucial role in enhancing defenses against sophisticated threats. This dynamic position involves collaborating with various teams to simulate realistic threat scenarios and conducting in-depth research to uncover vulnerabilities. You'll provide actionable insights that empower teams to strengthen their detection and response capabilities. If you're passionate about cybersecurity and eager to make a significant impact in a collaborative environment, this opportunity is perfect for you.

Qualifications

• Experience in cybersecurity with a focus on adversary simulation and red/purple teaming.
• Strong understanding of attack techniques and threat actor methodologies.

Responsibilities

• Collaborate with Cyber Defense teams to simulate real-world threats.
• Conduct adversarial research to identify potential security gaps.

Skills

Cybersecurity

Adversary Simulation

Red Teaming

Security Research

Analytical Skills

Communication Skills

Education

Relevant Certifications (OSCP, OSEP, etc.)

Job description

Get to know Okta

Okta is The World’s Identity Company. We free everyone to safely use any technology—anywhere, on any device or app. Our Workforce and Customer Identity Clouds enable secure yet flexible access, authentication, and automation that transforms how people move through the digital world, putting Identity at the heart of business security and growth.

At Okta, we celebrate a variety of perspectives and experiences. We are not looking for someone who checks every single box - we’re looking for lifelong learners and people who can make us better with their unique experiences.

Join our team! We’re building a world where Identity belongs to you.

The Okta Security team’s mission is to strengthen Okta’s position as the leading Identity-as-a-Service solution through identifying and resolving risks to our employees, products, and most importantly, our customers. With the ever-increasing pace of cloud application adoption, companies are struggling to find ways to accurately assess risk and act at the speed of their business.

In addition to driving security in our Corporate environment and the Okta service, the Security team is deeply entrenched in the Okta business. As such, we contribute to product roadmaps, branding, research and other strategic aspects of our operations. We work across multiple functions, business partners and the research community. We are an engineering-focused team that seeks to stay on the cutting edge of security technology and the threat landscape.

The Role

The Adversarial Engineering and Operations team is integral to Cyber Defense’s intelligence-led strategy to safeguard Okta’s infrastructure, products and customers. We specialize in planning and executing adversarial operations alongside Defensive Cyber Operations, simulating sophisticated threat actors and scenarios to provide critical insights into Cyber Defense’s ability to detect and respond to threats.

We’re seeking a highly skilled operator to join our global team. In this role, you’ll be responsible for planning, executing, and delivering adversarial operations and research engagements. You’ll work directly with Defensive Cyber Operations to simulate realistic threat scenarios, analyze security gaps, and uncover areas where we can strengthen our detection and response capabilities.

This is not a penetration testing or traditional red team role. While you may identify vulnerabilities or weaknesses in our infrastructure, the primary purpose of this role is to provide actionable insights and enhance our overall ability to detect and respond to sophisticated threats.

Core Responsibilities:

• Collaborate Across Cyber Defense: Work closely with various teams within Cyber Defense, including Defensive Cyber Operations, to simulate real-world threat scenarios.
• Simulate and Document Attacker Behavior: Replicate sophisticated adversary tactics to enhance threat detection and response strategies, ensuring real-world scenarios are accurately represented.
• Conduct Adversarial Research: Perform in-depth research on Okta’s products and platforms from an adversarial perspective to identify potential avenues of exploitation, abuse, and overlooked attack vectors.
• Provide Actionable Insights: Translate adversarial operations and research into actionable recommendations that empower teams to implement proactive detection strategies and improve incident response workflows.
• Partner Across Teams: Collaborate with the broader security and engineering teams to share findings, highlight security gaps, and drive improvements.
• Document and Present Findings: Clearly document research, adversarial operations, and results, presenting actionable insights to stakeholders at all levels.
• Contribute to Program Development: Drive the continuous improvement of the Adversarial Engineering and Operations program by developing internal tools, methodologies, and processes that enhance our approach and capabilities.

What does it take?

You’re a team player with excellent communication skills and a deep curiosity for understanding complex systems. You know that to defend a system effectively, you must first understand how it works. You enjoy testing assumptions, uncovering hidden risks, and making your own life harder in the process.

You come from a strong offensive security background, with experience in red or purple team roles. However, you're now looking for an opportunity to work more closely with defensive teams, using your skills to help build stronger, proactive defenses. You’re well-versed in attacker techniques, and can articulate how they work and how they can be detected and investigated. You don’t just identify problems — you’re motivated to partner with others across teams to drive solutions.

You have experience working with remote teams and can remain self-motivated and focused, contributing effectively outside of a traditional office environment.

Skills and Experience

• Proven experience in cybersecurity and/or related fields, with hands-on expertise in adversary simulation, red/purple teaming, or security research.
• Proven experience simulating attacker behavior in SaaS applications, user endpoints, and cloud environments, including containerized infrastructure.
• Strong understanding of cybersecurity principles, attack techniques, and threat actor methodologies.
• Analytical mindset, with excellent problem-solving skills to uncover potential risks and improve detection and response.
• Outstanding communication and collaboration skills, with the ability to work effectively across teams and geographies.
• Relevant certifications are a plus (OSCP, OSEP, OSMR, GXPN, GDAT, etc)

Okta is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, ancestry, marital status, age, physical or mental disability, or status as a protected veteran.