Adaptive Security

Adaptive Security

Adaptive Security is an AI-driven security awareness platform that defends organizations against AI-powered social engineering. Adaptive Security runs hyperrealistic simulations of deepfake voice calls, smishing, and email spear-phishing, then trains employees and scores their risk over time. Founded in 2024 by the team behind marketing-tech company Attentive, Adaptive Security became the OpenAI Startup Fund's first cybersecurity investment. It targets security teams worried that attackers can now clone an executive's voice or face, and it pairs realistic attack drills with automated phishing triage and organization-wide risk dashboards to reduce human-factor breaches.

Production credibility: Founded in 2024 in New York by Brian Long (CEO) and Andrew Jones (CPO), serial entrepreneurs who previously co-founded Attentive (grown to 8,000+ customers and $500M+ revenue) and TapCommerce (acquired by Twitter). Raised a $43M Series A in April 2025 co-led by Andreessen Horowitz (a16z) and the OpenAI Startup Fund — OpenAI's first cybersecurity investment — with Abstract Ventures, Eniac Ventures, CrossBeam Ventures, and K5. Followed by an $81M Series B in December 2025 led by Bain Capital Ventures, with NVentures (NVIDIA), OpenAI Startup Fund, a16z, Abstract Ventures, Capital One Ventures, and Citi Ventures, bringing total funding to approximately $146.5M. The company reports 150+ employees.

Key Features

• Deepfake simulation attacks delivered over voice calls, SMS, and email
• Hyperrealistic phishing and spear-phishing campaigns tailored per employee
• AI-generated training content that adapts to emerging social-engineering tactics
• Automated phish triage and classification of reported messages
• Dynamic employee risk scoring at individual, team, and organization levels
• Real-time detection and mitigation of active phishing threats
• Compliance-oriented reporting and dashboards for security awareness programs

Ideal Use Case

A company fears attackers will impersonate its CFO with a cloned voice, so it uses Adaptive Security to run deepfake vishing drills, train staff who fall for them, and track risk reduction across departments.

How Adaptive Security differentiates

Adaptive Security reframes the security-awareness category — long held by KnowBe4 and Proofpoint — around AI-generated threats, simulating deepfake voice and video that legacy phishing-test tools don't replicate. Its edge is realism and adaptive content rather than the static annual training modules incumbents are known for. Unlike LLM-guardrail vendors such as Virtue AI or WitnessAI, Adaptive secures the human layer (employees targeted by scams) rather than the model layer (what an LLM outputs). The trade-off is that it addresses social engineering and awareness, not data governance or runtime model defense, so it complements rather than replaces those AI-security tools.

FAQ

Q: What does Adaptive Security do? A: Adaptive Security is an AI-driven security awareness platform that simulates deepfake, vishing, smishing, and phishing attacks, trains employees, and scores organizational risk to reduce social-engineering breaches.

Q: Who founded Adaptive Security? A: It was founded in 2024 by Brian Long (CEO) and Andrew Jones (CPO), who previously co-founded the marketing-tech companies Attentive and TapCommerce.

Q: How much has Adaptive Security raised? A: Adaptive Security raised a $43M Series A in April 2025 (a16z and OpenAI Startup Fund) and an $81M Series B in December 2025 (Bain Capital Ventures), bringing total funding to roughly $146.5M.

Q: Is Adaptive Security backed by OpenAI? A: Yes. The OpenAI Startup Fund co-led its $43M Series A — OpenAI's first cybersecurity investment — and also participated in the later $81M Series B.

Q: Adaptive Security vs KnowBe4: what's different? A: Both run security-awareness training, but Adaptive focuses on AI-generated threats like deepfake voice and video simulations, where KnowBe4 is the established player built mainly around traditional phishing tests and training libraries.

tl;dr

Adaptive Security is an AI-driven security awareness platform that simulates deepfake, vishing, and phishing attacks and trains employees against them. Founded in 2024 by Attentive's founders, it raised $43M (a16z, OpenAI) and an $81M Series B, totaling about $146.5M.

Related

Looking for more options? Browse the Security & Governance directory or read our best AI security tools listicle. Adaptive Security is also tracked on Crunchbase.