Investing in Adaptive Security

In today’s fast-moving cybersecurity landscape, one fact is consistent: the human factor remains a critical security challenge. Employees are still a primary entry point, and existing training methods — such as annual compliance courses and generic phishing simulations — simply aren’t up to the job of preventing today’s threats. With just a few clicks, for example, attackers can launch thousands of AI-driven deepfake personas, indistinguishable from trusted colleagues, and rapidly target entire organizations.

These threats aren’t hypothetical, and CISOs across industries identify AI-powered social engineering as a critical concern. However, AI’s role in the cybersecurity ecosystem is not limited to cyberattacks — it’s also a valuable tool to defend against those threats. Throughout history, game-changing technologies have been used for both good and bad, and AI is no exception. The difference this time is that AI can give security teams an incredible improvement in efficiency, enabling them to anticipate, adapt, and intervene in ways previously impossible. This gap between outdated methods and real-world attack readiness presents a massive opportunity for a new category of AI-native solution.

Adaptive Security was founded directly in response to this unprecedented challenge of harnessing AI to proactively protect enterprises. Adaptive is creating an entirely new category of cybersecurity solutions, specifically engineered to anticipate, prevent, and mitigate AI-powered threats before they materialize.

Adaptive Security’s platform provides organizations with the tools to:

• Realistic adversary emulation: Adaptive uses generative AI to create dynamic simulations that mirror how attackers operate today — through voice cloning, SMS impersonation, email spoofing, and more. These aren’t static phishing tests; they’re fluid, multi-channel exercises customized to each company’s threat model.
• Custom-tailored AI-powered training: Instead of generic security content, Adaptive delivers adaptive learning based on individual employee behaviors and risk profiles. 
• Behavioral reinforcement in real time: When employees interact with a simulated threat, they get in-the-moment guidance—turning every test into a teachable moment.
• Operational visibility and AI-driven response: Adaptive’s risk engine continuously ingests signals from across the org—emails flagged, calls made, links clicked—and turns it into real-time threat intelligence. Security teams gain an evolving risk picture they can act on immediately.

Adaptive was founded by Brian Long and Andrew Jones, serial entrepreneurs who previously built Attentive into a massive business with over 8,000 enterprise customers. When Brian came by our SF office to record a podcast on AI security, he had on a well-worn Nine Inch Nails t-shirt. After a few casual questions about the shirt and a very long conversation about how Trent Reznor not only founded Nine Inch Nails, but also produced a number of soundtracks and albums for other artists, it became clear he held a deep respect for Reznor as a builder and creator. Brian’s admiration for obsessive founders that can’t sit still and his own relentless drive to keep building great things is why he’s our kind of founder. 

We’re thrilled to lead Adaptive Security’s Series A, and to support Brian, Andrew, and the entire Adaptive Security team as they scale their vision to equip enterprises to confront — and outsmart — the new generation of cyber threats.