Leading the Agentic Era: 5 Key Takeaways on the Future of Workforce Development

The pace of AI innovation, the rise of agentic systems, and the continued pressure on organizations to prove resilience are changing what security leaders need from workforce development.

Our webinar, “Leading the Agentic Era: Inside HTB’s New Enterprise Model for Cyber Readiness,” explored what this shift means for enterprises, government organizations, and practitioners preparing for the next generation of cyber threats.

Hosted by Petros Perselis, SVP of Customer Success at Hack The Box, the session featured members of our leadership team, including Christine Bartlett, SVP of Marketing, Gibb Whitman, President, and Gerasimos Marketos, Chief Product Officer. Together, they discussed our recognition as a Leader in the 2026 Forrester Wave™, the growing importance of agentic AI readiness, and the role of hands-on, measurable training in helping security teams move from theoretical knowledge to operational confidence.

Let’s dive into five of the most interesting topics and takeaways from the discussion.

1. Why hands-on experience is becoming essential for cyber readiness

The market has moved beyond passive cybersecurity training. Security leaders need environments that reflect how teams actually operate when facing real threats.

That means high-fidelity labs, real-world scenarios, and collaborative exercises where practitioners can learn by doing. The goal should be to build the judgment, confidence, and speed needed to act under pressure.

Christine Bartlett, SVP of Marketing at Hack The Box, captured the shift:

“That shift signals an increased demand in the market to not just simply train your cybersecurity workforce with multiple choice questions or video. It needs to be real-life simulations where folks are actively learning. There’s a teaming environment, and we like to look at it in a holistic, programmatic approach: how are your teams learning tactically, operationally, and strategically?”

This is especially important as cybersecurity teams become more cross-functional. Offensive practitioners need to understand defensive workflows. Blue teamers benefit from understanding attacker behavior. Teams need to collaborate across disciplines, not train in silos.

Hands-on environments allow teams to fail safely, learn quickly, and return to their organizations better prepared to respond when it matters.

“Teams need the ability to train and practice with high-fidelity labs and scenarios that simulate real-world activation. So folks can fail fast, learn, build that confidence, and then give back to their teams so they can move faster operationally.”

2. AI is raising the bar for human cyber expertise

Does the rise of AI in cybersecurity mean the importance of human skill is reduced? Actually, it increases the need for it.

AI-enabled tools can support faster analysis, automation, and decision-making, but they still depend on skilled practitioners who understand the context, know how to evaluate outputs, and can apply judgment in complex environments.

The cyber workforce remains the most important line of defense. Security professionals are responsible for selecting, configuring, using, and extracting value from the tools deployed across the enterprise — including AI.

Gibb Witham, President at Hack The Box, emphasized the importance of human context:

“The human security context and domain knowledge is incredibly important to be able to leverage the benefits of AI, as well as familiarity with using AI to augment our customers’ ability to navigate in this new paradigm.”

That has major implications for security leaders. AI adoption should not be treated as a shortcut around workforce development. Instead, upskilling becomes the foundation for getting meaningful value from AI-enabled security operations.

Skilled practitioners can use AI to move faster and work more effectively. Less prepared teams risk misunderstanding outputs, automating weak processes, or introducing new operational blind spots.

3. Agentic AI readiness is becoming a new enterprise priority

A major theme of the discussion was the emergence of agentic AI readiness: the ability to prepare people, teams, and systems for a future where AI agents play a larger role in cyber operations.

This readiness challenge has two sides.

The first is security for AI: learning how to secure, test, red team, and defend AI systems. That includes generative AI, but also traditional AI and machine learning systems that are already embedded across many organizations.

The second is AI for security: helping practitioners understand how to use AI to become more effective in offensive, defensive, and operational workflows.

Gerasimos Marketos, Chief Product Officer at Hack The Box, explained the distinction:

“When we’re talking about AI security, we can break this down into two things. It comes down to security for AI, which means how we secure AI systems, how we defend AI systems, how we test AI systems. And there is also AI for security, which means when it comes to pentesters, SOC analysts, blue teamers, what do they need to know in order to be more effective and efficient in their job?”

This is where agentic systems introduce a new layer of complexity. Enterprises need to understand how AI agents perform in realistic cybersecurity scenarios, where they succeed, where they fail, and how humans should work alongside them.

“The fact that it’s AI doesn’t mean that it necessarily performs on the level that it should be performing. Organizations and vendors need an environment where they can plug in these agents or LLMs and understand how they perform and how they can improve the capabilities of these models or agents.”

For security leaders, the implication is clear: AI agents need to be benchmarked, tested, and improved in purpose-built environments. Readiness can no longer focus only on humans or tools in isolation. It must account for how humans and AI systems perform together.

4. The biggest AI gains come when skilled humans are in the loop

One of the most compelling insights from the webinar came from our large-scale CTF evaluation comparing human-only teams with AI-augmented human teams.

Across the overall participant population, AI-augmented teams completed cybersecurity challenges faster. But the most interesting finding was what happened as skill levels increased: the performance gains grew significantly among stronger practitioners.

“There was a 40% uplift in speed of completing various security challenges. But as you started to compare the different skill levels — the top 50%, top 20%, top 10% — that relationship went up nonlinearly. If you take someone who is highly skilled or even intermediate skilled, we found on average a two to four times increase, and in some cases on specific challenges, a 30 times increase in performance.”

This reinforces an important point for enterprise security programs: AI does not create expertise on its own. It amplifies the capabilities of people who already have the right foundation.

The better the practitioner understands the domain, the better they can prompt, validate, challenge, and operationalize AI output. That means the future of cyber readiness is not just about adopting AI tools. It is about building teams that know how to use those tools effectively.

5. Measurable readiness is replacing completion-based training

How do you know your security team is actually getting better? Completion rates and engagement metrics can tell part of the story, but security leaders need evidence that teams are becoming more capable.

That is why measurable readiness was a recurring theme throughout the webinar. Hands-on learning becomes most valuable when it connects to real operational outcomes: job readiness, framework alignment, team performance, and metrics that executives and boards can understand.

The discussion highlighted three areas that matter most to security leaders: realistic performance conditions, proof of job readiness, and workforce alignment to recognized frameworks such as MITRE ATT&CK and NIST.

Security leaders are looking for three things. The first one is they want to make sure that their teams perform under realistic conditions. The second one is around job readiness, which means people can follow certifications, paths, and collections and prove that they’re ready to perform in a real-world environment. And the third layer is workforce alignment to recognized frameworks like NIST, NICE, and MITRE.

This is also where reporting becomes critical. As cyber readiness becomes more strategic, organizations need unified visibility across individual learning, team-based exercises, CTF performance, and operational simulations.

A CISO needs the big picture: where the organization is strong, where the gaps are, and whether teams are improving over time. Team leads and power users need the ability to drill down into specific strengths, weaknesses, and role-based progress.

The future of cyber workforce development will be measured less by whether people completed training and more by whether they can prove readiness in realistic, high-pressure environments.

Final takeaway

The agentic era is changing what cybersecurity readiness looks like.

Organizations need practitioners who can operate confidently in realistic conditions, security teams that can collaborate under pressure, and leaders who can measure whether their workforce is prepared for AI-enabled threats.

The central message from the discussion was clear: the future of cyber resilience will depend on the combination of human expertise, AI capability, and measurable hands-on readiness.

As organizations evaluate how to build and measure readiness in this new landscape, independent industry research can provide valuable guidance. To learn more about the trends shaping cyber workforce development and why Hack The Box was recognized as a Leader, explore the 2026 Forrester Wave™ report using the link below.

Read the report Watch the full session