Name: Benchmarking AI Models: Metrics, Evaluations & Leaderboards
Start: 2026-03-25T16:00:00Z
End: 2026-03-25T16:01:00.000Z
Location: BrightTALK

Hack The Box provides a human-first platform creating and maintaining high performing cybersecurity individuals and organizations.

This technically focused webinar explores AI red teaming—stress-testing AI models and agents to uncover real vulnerabilities. We’ll examine common attack techniques such as prompt injection, jailbreaks, tool abuse, and exploit chaining that can push AI systems beyond their intended behavior.

Using real-world examples, attendees will learn a structured approach to adversarial AI testing, from crafting malicious inputs to identifying model blind spots and safety bypasses. The session also shows how red team findings can be used to strengthen AI systems through tuning and mitigation.

Ultimately, this webinar demonstrates why breaking your AI is often the fastest way to make it safer—and how Hack The Box provides a controlled environment to do exactly that.

Red Teaming AI systems: How to break your AI (before attackers do)

AI agents are rapidly entering cybersecurity operations but their real-world effectiveness often lags behind the hype. This webinar examines what AI agents can genuinely do today, where expectations exceed reality, and why fully autonomous security workflows remain rare despite growing adoption.

The discussion will unpack recent findings where AI agents struggled with real-world security tasks, drawing on results from the Neurogrid CTF to ground the conversation in practical evidence. Attendees will explore why both attackers and defenders are racing to leverage AI, how to cut through the noise, and where meaningful opportunities actually exist.

AI agents in cybersecurity: hype vs. reality

Hack The Box and LinkedIn Learning have teamed up to bring a first-of-its-kind, hands-on cybersecurity curriculum to millions of learners.

The partnership delivers 11 interactive, browser-based labs embedded directly inside LinkedIn Learning; these courses let learners launch safe, realistic attack/defense simulations with a single click — no additional logins, tooling, or setup required.

The curriculum was designed exclusively for LinkedIn Learning to bridge foundational knowledge with practical skills across both offensive and defensive domains, preparing purple-minded analysts to detect, investigate and respond to modern, AI-augmented threats.

Join Hack The Box and LinkedIn Learning for a live webinar that walks through the curriculum, demonstrates how the labs work inside the LinkedIn Learning experience, and explores how organizations and learners can benefit from embedded, hands-on skills development.

Building job-ready cybersecurity analysts with HTB & LinkedIn Learning

Join Hack The Box experts to explore how AI is reshaping cyber risk, security roles, and organizational readiness in 2026. A strategic webinar for security leaders.

What you’ll learn:
- How AI is reshaping the security threat landscape and what that means for organizational risk in 2026
- Where AI capabilities are often over-assumed, creating gaps between adoption and actual readiness
- How security roles, responsibilities, and team structures are evolving in AI-enabled environments
- How AI red teaming can be used to evaluate and validate readiness before AI capabilities are deployed at scale

AI Security in 2026: Trends, Roles, and Readiness

Join this webinar to see how CTEM insights can be transformed into hands-on readiness. Discover how teams practice responding to incidents in a gamified, realistic environment.

Mind the gap: Turning exposure data into real-world readiness

Hack the Box and LetsDefend sit down for a fireside chat on what their partnership means for enterprise blue teams. Learn how unified hands-on training, SOC simulations, and integrated reporting will shape the next phase of defensive readiness.

Hack the Box x LetsDefend: Empowering the next blue era

OT and ICS environments are increasingly under attack, yet remain overlooked in many CTEM programs. Join Hack The Box and Dragos this November for a free webinar exploring real-world OT threats, the human readiness gap, and how to close it through hands-on CTEM training.

ICS in the crosshairs: Emerging threats in OT Environments

Learn how Scattered Spider operates, uncover their techniques, and practice detection in a follow-along investigation. Join our free webinar this October for insights and an interactive walkthrough of one of today’s most disruptive adversaries.

Dissecting Scattered Spider: A hands-on guided walkthrough

CTF-style benchmarking competitions are no longer just for fun, they’ve become critical tools for assessing cybersecurity readiness, identifying technical gaps, and guiding upskilling strategies.
In this webinar, Hack The Box experts will walk through the highlights of the Cyber Skills Benchmark Report 2025, based on performance data from this year’s Global Cyber Skills Benchmark.

Beyond the Competition: What the 2025 Global Cyber Skills Benchmark Revealed

Join us for a deep dive into the 2025 edition of the Cybersecurity Professional Development Buyers Guide by Hack The Box. In this session, we’ll walk you through the five key trends reshaping how organizations evaluate, purchase, and implement cybersecurity training solutions.

From overcoming outdated methods to securing leadership buy-in, this webinar is designed to help buyers make smarter, ROI-driven decisions. Discover what 850+ global organizations are doing to future-proof their teams, reduce human-related risks, and align training to real business goals, not vanity metrics.

Cybersecurity Training Platforms Buyers Guide 2025

Join our security experts for the final session of the Benchmarking Masterclass Series to uncover actionable strategies and real-world examples for building threat-informed training programs that close skill gaps and strengthen team readiness.
Discover how leading organizations are transforming fragmented, individual-led efforts into structured programs that prepare entire teams to tackle emerging threats while aligning with unique security goals.
Through specific examples of training paths, time management strategies, and progress measurement techniques, you’ll gain the insights needed to create a high-performing, threat-ready workforce.

From Gaps to Greatness: Developing teams for a threat-driven future

Join the Benchmarking Masterclass Series to uncover how dynamic, real-world benchmarking approaches can prepare your organisation for today's evolving threats.
Our second webinar in the series dives into the practical side of dynamic benchmarking, providing actionable insights to assess team readiness and close critical skill gaps. Register today to learn how to turn benchmarking into measurable improvements for your team.

From Theory to Action: Applying dynamic benchmarking to real-world threats

Traditional benchmarking methods, such as static metrics and certifications, are no longer enough to protect your organization against the rapidly evolving threat landscape. For cybersecurity leaders managing team readiness, adopting dynamic, real-time approaches is essential to accurately assess and strengthen capabilities in today’s complex threat environment.
Join us for the first session of the Benchmarking Masterclass Series, featuring experts from Tesco Bank and Accenture. Together, we’ll challenge outdated benchmarking methods, uncover the limitations of traditional approaches, and explore why continuous, real-world benchmarking is essential for building cyber resilience.

Rethinking Readiness: Benchmarking skills to build true cyber resilience

The cybersecurity industry is booming, yet the talent gap continues to widen. With threats evolving and organizations prioritizing digital defense, there’s a growing demand for skilled professionals to fill critical roles. For those in the military, federal service, or even private industry, transitioning into cybersecurity offers the chance to build a dynamic and impactful career. But where do you begin?

A panel of experts, featuring leaders from military, federal, education, and private-sector cybersecurity roles, will provide a candid look at the opportunities and challenges of transitioning into the cyber domain. You'll hear firsthand experiences from professionals who have made this career move and gain insights into what worked for them—and what pitfalls to avoid.

Career Transition into the Cyber Domain

Think your organization is secure? Think again. Cyber threats are evolving fast, especially in the financial sector, where gaps in operationalizing intelligence leave many vulnerable. Join us for an eye-opening webinar that reveals how to bridge the gap between threat intelligence and real action with the MITRE ATT&CK framework. We’ll show you how to maximize your CTI and SIEM tools, prioritize essential skills development, and tailor your team’s defenses to outsmart adversaries. Don’t miss this chance to transform your cybersecurity strategy.

The Uncomfortable Truth About Your Organization and MITRE ATT&CK

Get ready for evolving cyber threats with hands-on simulations in a realistic scenario. Strengthen your team's defense and attack skills on critical systems.

Firewall and Order: Defending Veloria's Digital Frontier with Hack The Box

Join Hack The Box experts for an insightful webinar exploring the positive effect of Capture the Flag (CTF) events on cybersecurity workforce development and the organizations these professionals protect. 

Learn how collaboration is fostered and gamified challenges can be applied in a real-world environment, all with a benchmark CTF. Open and relevant to everyone from entry-level cybersecurity professionals to CISO leaders, this is a session you won’t want to miss if you’re looking for an effective training program.

Beyond the Competition: How CTFs shape cybersecurity talent development.

As organizations experiment with AI in security, a key challenge is measuring whether AI agents are actually effective and improving over time.

This webinar focuses on benchmarking and evaluation methods for AI in cyber operations, exploring which performance metrics truly matter—from threat detection accuracy and exploit success rates to response speed and reliability. We’ll also walk through Hack The Box’s AI Range methodology, showcasing board-ready scorecards and leaderboards that compare AI models on common security scenarios, such as an OWASP Top 10 web application framework.

Attendees will learn how to validate AI security performance and make data-driven decisions when investing in AI-driven security tools.

Benchmarking AI Models: Metrics, Evaluations & Leaderboards

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Benchmarking AI Models: Metrics, Evaluations & Leaderboards

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