In cybersecurity, some bugs hide in plain sight. To get ahead of attackers, CISOs rely on penetration testing (pen testing) by simulating real-world exploits. Pen testing is effective, but it’s also one of the slowest, most manual, and only gives you a snapshot in time while the environment keeps changing.
Gartner and others believe $6 to $7 billion will be spent globally on pen testing by 2032. We’ve heard many companies routinely spend six to seven figures annually on pen testing, only to receive one-off reports that are often outdated before they’re sent. As software release cycles accelerate thanks to AI, pen testing just hasn’t kept up.
This summer, we talked to dozens of leading CISOs from large and public enterprises, and nearly every single one said they wanted a new pen testing solution. CISOs found that they couldn’t rely on fully autonomous solutions, and with a 4.8M workforce gap in security services, they needed a solution that would enhance their existing team.
Penetration testing is a universal need in security. However, many early attempts in the AI version of this category failed because buyers were resistant, pricing didn’t align with expectations, or the technology was too rigid to fit customers’ existing needs.
This is precisely why we are so excited to announce that Felicis has led Terra Security’s Series A, and Jake has joined the board of directors.
Terra Security is a perfect example of how AI can augment labor in the security sector. Terra’s platform goes beyond simulating attacks. It orchestrates a swarm of over 70 specialized AI agents that behave like real adversaries. These agents combine deterministic code analysis with LLM-driven reasoning to uncover complex vulnerability chains that traditional tools often miss. The result is a system that’s thorough and dramatically more scalable than traditional pen testing consulting services. Terra offers both periodic tests and continuous monitoring, and their solution can scale up for always-on deployments.
We first met CEO Shahar Peled at an AWS re:Inforce dinner, after a Felicis founder introduced us. This person was raving about Shahar, calling him a rare breed of founder with deep technical chops and the unusual ability to connect directly with CISOs. That night, every CISO at the table wanted to talk to Shahar.
Terra’s approach has won them impressive recognition: just a few months ago, the team took first place in the 2025 CrowdStrike and AWS Cybersecurity Accelerator competition, held in partnership with NVIDIA Inception. The competition was judged by industry leaders CJ Moses (Amazon CISO), George Kurtz (CrowdStrike CEO), and David Reber (NVIDIA CSO).
Since then, Shahar and co-founder Gal Malachi have built a relentless culture of execution. Shahar and Gal are founders with extreme bias to action, are constantly shipping and iterating, and have a keen understanding of the promise and limits of AI-powered pen testing.
Augmented → Autonomous
While many CISOs want a fully autonomous pen testing solution, they’ll admit that AI isn’t ready to fully take over and that a human needs to be kept in the loop. And the autonomous pen testing solutions right now aren’t able to offer the kind of deep analysis CISOs require or competitive pricing because of the steep costs of compute.
Shahar and Gal’s ambitious product vision is anchored in today’s buyer needs: human-augmented pen testing that fits smoothly into existing teams and budgets. Pen testing today is like the early days of self-driving cars - starting with humans still in control, with the goal of reaching full automation after years of progress.
Today, Terra gives customers a fast, 10X boost to their security posture, while they focus on building fully autonomous pen testing over time.
With this new round of funding, Terra is expanding its R&D hub in Israel and the US, while scaling its GTM team. In less than a year, Terra has been moving impressively fast, and we’re excited to support their continued speed of execution and smart expansion.
Terra is already working with a great batch of customers (including Fortune 500 companies), and 100% of them have converted from being early design partners. We’re honored to lead this round and invest alongside Dell Technologies Capital, SVCI, and existing investors SYN Ventures, LAMA Partners (fka FXP), and Underscore VC. Terra is also adding incredible angels to the cap table, including Ofer Ben-Noon and Ohad Bobrov of Talon Security, Google VP of Research Yossi Matias, and Sysco CISO Charles Tango. Security veteran Gerhard Eschelbeck (former CISO at Google) has joined the board after evaluating many players in the space, a strong signal of Terra’s unique positioning.
We believe Terra will define the next era of offensive security as a whole and pen testing in particular, one where AI doesn’t just augment humans, but unlocks a new level of adversarial simulation that’s scalable, proactive, and deeply pragmatic.
