Aug 11, 2026
Introducing the AI Red Teaming Upskill Program
Introducing AI Red Teaming Upskill Program. New way to build AI security capabilities across teams with different roles and levels of experience.
AI introduces new attack paths, requiring security teams to assess AI systems, as well as the applications, APIs, cloud environments, and identity systems surrounding each deployment.
This makes AI security an immediate workforce priority. Your organization needs people who understand how these systems can be attacked, how weaknesses across the wider environment can be combined, and how to test whether security controls hold up in practice.
Your Challenge: Building those capabilities across teams with different roles and levels of experience.
- Hiring specialists can add expertise, but the available talent pool is limited and hiring alone is difficult to scale.
- Giving everyone access to the same course does not account for existing skills or confirm that your team has the necessary foundations.
OffSec’s new AI Red Teaming Upskill Program, available with Learn Enterprise, provides a structured way to develop expertise internally. It assesses what each security team member already knows, assigns a role-aligned development path, and tracks progress toward the AI Red Team Operator role.
Your existing workforce already has skills that can contribute to AI security. Penetration testers understand exploitation, security engineers know your architecture and controls, and infrastructure teams understand the environments supporting AI applications. The opportunity is to build on that existing knowledge.
Without a structured development path, you must manually:
- Determine which employees are suitable
- Identify their individual knowledge gaps
- Select the right content
- Judge when they are ready to advance
That approach becomes difficult to manage across larger teams and often produces inconsistent results.
The AI Red Teaming Upskill Program automates this process into one guided experience. You can place employees at the appropriate level, focus training on the skills each person needs, and follow their development through a consistent progression model.
AI security cannot be separated from the wider environment in which AI systems operate. Practitioners may need to assess the application layer, APIs, cloud infrastructure, containers, identity systems, and other technologies surrounding an AI deployment.
The AI Red Teaming Upskill Program addresses these skillsets through six stages:
- Foundations of Cybersecurity & Computing
- Offensive Security & Web/API Attacks
- Cloud, Containers & Modern Infrastructure
- Red Team Operations: AD Lateral Movement & Evasion
- LLM Red Teaming
- Advanced AI Red Teaming
Your organization can leverage the Upskill program to streamline development standards while accommodating employees at every experience level.
The AI Red Teaming Upskill Program provides a repeatable process that you can apply across teams.
Each learner completes a placement assessment that evaluates current competencies and recommends the appropriate starting stage.
Learners can test out of earlier stages when they demonstrate the required skills. This helps you avoid assigning unnecessary training and direct development time toward the areas that need attention.
Learners complete job-role-aligned modules and hands-on labs within each stage. Content builds toward the technical responsibilities of the next role instead of presenting employees with an open catalog and leaving them to determine what to study.
This provides managers a ready-made progression path and creates a more consistent learning experience across the workforce.
Optional four-hour stage assessments use objective-based grading to verify readiness for more advanced work. Learners who achieve at least 70% of the assessed objectives confirm that they are prepared to move forward.
The final stage concludes with Synthetic Siege, an AI-300 Challenge Lab that assesses practical application. Learners can complete the Upskill Program without taking a separate certification exam. The associated certification remains available for employees who choose to pursue it.
The platform tracks skills and progress at each stage. Overall program completion includes both learning content and assessments.
You gain a clearer view of how employees are progressing toward the AI Red Team Operator role, rather than relying only on enrollment numbers or course completion.
The program gives you a practical way to build specialized capability internally while making workforce development easier to target, manage, and measure.
Rather than relying solely on external hiring, you can identify promising employees, develop them through a structured progression, and prepare them for increasingly specialized AI security responsibilities. Placement assessments show which employees already possess relevant skills and how much additional development they require. You can use that information to identify internal candidates for AI security responsibilities and assign training based on demonstrated needs.
The Upskill program empowers leaders to train the right people at the right level. Employees begin at the stage that reflects their current abilities. Experienced practitioners avoid repeating foundational content, while less experienced learners receive the preparation they need before entering advanced training.
The six-stage structure establishes a common set of skills for progression toward the AI Red Team Operator role. Your managers can evaluate readiness against the same standard without creating separate development plans for every employee.
Hands-on labs and objective-based assessments provide more insight than content completion alone. Your employees work through practical exercises and demonstrate the skills associated with each stage.
The AI Red Teaming Upskill Program is the first program delivered through OffSec’s new Upskill Programs experience. The same stage-based model can support additional roles and technical domains as your priorities change.
Through Learn Enterprise, you can combine structured Upskill Programs with hands-on labs, Cyber Ranges, custom Learning Paths, progress tracking, and industry-recognized certifications. This gives you a repeatable way to translate workforce priorities into defined development journeys.
You no longer have to choose between searching for specialized AI talent and hoping employees are ready for advanced training. Assess existing skills, build missing capabilities, validate progress, and develop AI red teamers through one structured program.