Anagram Security

Anagram Security (legal name Enigma Analytics, Inc.) is a New York-based cybersecurity startup building a human-driven security platform that replaces the dreaded once-a-year compliance video with bite-sized, gamified microlearning and adaptive phishing simulations. Founded by Harley Sugarman and formerly known as Cipher, the company takes design cues from TikTok, Duolingo, and Khan Academy to make employees the strongest link in security rather than the weakest. It raised a $10M Series A led by Madrona in February 2025, serves Fortune 500 customers including Disney, Pfizer, Thomson Reuters, and MassMutual, and supports over 500,000 users worldwide.