Adaptive Security is a New York-based cybersecurity startup focused on defending enterprises against AI-powered social engineering. Founded in 2024 by Brian Long (CEO) and Andrew Jones (CPO), the team previously built mobile ad startup TapCommerce (acquired by Twitter) and SMS marketing company Attentive.
The platform provides AI-driven phishing simulations and security awareness training that go beyond traditional email-only attacks. It simulates deepfake voice and video calls, AI-generated vishing and smishing, and multi-channel social engineering campaigns, then delivers role-specific, fully editable training modules to employees. The product is delivered as SaaS, with integrations into identity providers and security stacks used by mid-market and enterprise teams.
Adaptive Security publicly launched in January 2025 and announced a $43 million Series A in April 2025 led by Andreessen Horowitz and the OpenAI Startup Fund, which marked OpenAI's first investment in a cybersecurity company. Additional investors include Abstract Ventures, Eniac Ventures, CrossBeam Ventures, and K5, alongside executives from Google, Workday, Shopify, Plaid, and Paxos.
By mid-2025, the company reported more than 100 enterprise customers including First State Bank, Podium, the Dallas Mavericks, and BMC, and it was named to Fortune's Cyber 60 list later in the year. The team has grown across New York, Los Angeles, and San Francisco offices.
Compared with established awareness training vendors such as KnowBe4, Proofpoint, and Hoxhunt, Adaptive Security differentiates by treating AI-generated attacks as a first-class threat: it ships deepfake and voice-cloning simulations out of the box and uses generative models to spin up realistic, personalized campaigns at scale. Its main challenges are convincing buyers that AI-native simulations justify the switch from incumbents and keeping content ahead of rapidly evolving attacker tooling.