Penetration testing (pentesting), long the cornerstone of validating a company’s defenses, is being fundamentally rebuilt. What was once a slow, expensive, and episodic service is transforming into an intelligent, continuous, and integrated layer for modern infrastructure.

This isn’t just about automation; it’s about autonomy. And it’s an opportunity to redefine a foundational pillar of cybersecurity.

For decades, pentesting has been synonymous with human expertise. Elite red teams and consulting firms were hired for costly, time- and scope-boxed engagements to simulate attacks and uncover vulnerabilities before adversaries could. While deep, these assessments have been highly manual and disconnected from the pace of modern engineering.

In today’s development environment, that model simply cannot scale. Code deploys daily. Cloud permissions change hourly. The attack surface is expanding faster than humans can map.

Meanwhile, attackers are augmenting their own capabilities with AI, compounding the asymmetry between threat velocity and defensive readiness. Security leaders already know the current paradigm is broken. They do not need more annual or biannual point-in-time PDFs that are stale on arrival: they need persistent signal, contextual insights, and always-on adversarial testing.

A New Model Is Emerging

This shift can be understood as a three-act evolution, moving from a manual service toward truly intelligent infrastructure.

Phase 1 – Manual Services:
The original model relied on boutique consultancies and internal red teams delivering high-touch, labor-intensive projects. While technically rigorous, it was constrained by high costs ($25,000–$100,000 per test), slow delivery cycles that took weeks or months and a lack of scalability.

Phase 2 – Automation-Forward Platforms:
The last decade saw the rise of Penetration Testing as a Service (PTaaS) with platforms like Cobalt, Pentera, and Horizon3.ai productizing the workflow. They brought repeatability and speed, compressing testing cycles and broadening access. However, this was automation around pentesting — accelerating execution and reporting — not the automation of pentesting itself. The logic remained predefined and dependent on human input.

Phase 3 – Agentic, AI-Native Systems:
The current frontier, though early, is defined by agentic platforms built to emulate the creativity and persistence of real adversaries. These systems do not just automate steps: they autonomously reason through environments, adapt to context, and simulate dynamic exploit chains. By blending LLMs, symbolic reasoning, and exploit simulation, they move beyond known vulnerabilities to surface business-impacting attack paths.

This is a full-stack transformation: from point-in-time audits to persistent validation, from human bottlenecks to autonomous reasoning, and from siloed PDF output to embedded DevSecOps workflows.

Why Now? The Catalysts Driving Change

Several macro forces are accelerating demand for a new pentesting approach:

• Expanding Attack Surfaces: Cloud services, APIs, and SaaS tools have multiplied entry points, too many for humans alone to test effectively.

• Regulatory and Compliance Pressure: Evolving standards like PCI DSS 4.0 and HIPAA require more frequent and rigorous testing, driving demand for scalable, repeatable solutions.

• AI Adoption: AI boosts threat detection capabilities but also introduces novel vulnerabilities traditional pentesting cannot uncover.

• SecOps Burnout and Alert Fatigue: Security teams are drowning in alerts and triage queues. There is demand for tools that prioritize real risk and cut noise.

• Consulting Bottlenecks: Top-tier consulting firms are booked months in advance, forcing buyers to choose between delays or suboptimal tools. Agentic platforms offer elastic, on-demand alternatives.

Open Questions on the Road Ahead

The trajectory is clear. We are still early. For this category to mature, builders and investors must navigate key questions:

1. Can platforms overcome the trust gap?
   Security leaders are intrigued but cautious about granting autonomous systems broad access. Winning platforms will offer human-in-the-loop controls, transparent reporting, and safe, sandboxed execution. Regulators will need to decide what level of agentic involvement they will accept for compliance.

2. Who wins the battle for the buyer?
   Pentesting ownership is shifting from compliance-led to security-led mandates embedded in developer workflows. Developers, the new users, resist tools that do not fit cleanly into CI/CD pipelines. Will the winning model enhance existing service providers or target engineering and security teams directly with developer-first products?

3. Standalone platform or integrated feature?
   While agentic pentesting could emerge as a standalone category. The reality is that most tools today still have narrow vulnerability or attack surface coverage. Will they expand rapidly in scope, or be absorbed as features into broader security platforms?

Our Hill

We believe agentic pentesting is inevitable, rooted in a few core beliefs:

1. Security validation must be continuous and integrated.
   Annual testing is obsolete. Validation should live in CI/CD pipelines, cloud-native workflows, and runtime telemetry.

2. Trust will come through workflow utility.
   Adoption will begin with tool consolidation, not full autonomy, and grow as confidence builds.

3. The mid-market will drive adoption.
   Historically underserved by expensive consulting, SMBs and mid-market companies stand to benefit most. Agentic platforms democratize offensive security through better pricing and usability.

4. Exploitability will replace CVE count as the north star.
   Security teams want verified, contextual findings tied to real business impact, not noise.

The companies leading this shift are still in early stages, testing deployment models, pricing, and coverage. But the architectural pattern is converging: persistent agents, environment-aware context, and a real-time feedback loop is being embedded into how software is built and shipped.

Agentic platforms will not entirely replace red teams. But they are already reshaping where, how, and how often offensive validation happens, becoming the default for high-frequency workflows where legacy approaches fail to scale. The opportunity is clear: rebuild penetration testing from the ground up as intelligent, autonomous infrastructure.

If you are building it, we want to hear from you.

This article is for informational purposes only and does not constitute investment advice. Views expressed represent the opinions of the author and Jump Capital. Jump Capital may have investments in or pursue investments in the legal technology sectors discussed. References to specific approaches or technologies do not constitute investment recommendations.