# Harley Sugarman

> Harley Sugarman is the founder and CEO of Anagram, a New York security company rebuilding employee security training around behavior instead of boredom. A Stanford computer scientist and former Bloomberg Beta investor, he scrapped his original product and rebuilt it into a TikTok- and Duolingo-inspired microlearning platform that cut client phishing failure rates from 20% to 6% and won over Disney, Thomson Reuters, and MassMutual. Anagram raised a $10M Series A in 2025 led by Madrona.

- **Role:** Founder & CEO at Anagram Security
- **Organizations:** Anagram Security, Bloomberg Beta, Stanford University
- **Nationality:** American
- **Education:** B.S. in Computer Science, Stanford University
- **Known for:** Founded and leads Anagram, a human-driven security training platform reaching 500,000+ users, Raised a $10M Series A led by Madrona with General Catalyst, Bloomberg Beta, Operator Partners, and Secure Octane, Grew revenue from $0 to $1M within 12 months after the pivot

## Career timeline

- **pre-2022** — Entered college as an English major and semi-professional magician; later produced music videos before moving into engineering
- **pre-2022** — Software engineer at Bloomberg building infrastructure tools, then investor at Bloomberg Beta for two years focused on the future of work
- **2022** — Founded the company as Cipher, building capture-the-flag training for enterprise security teams
- **2024** — Pivoted in January 2024 from security-pro tooling to general employee security awareness after layoffs hit security teams
- **2025-02** — Rebranded to Anagram and announced a $10M Series A led by Madrona

## Achievements

- Founded and leads Anagram, a human-driven security training platform reaching 500,000+ users
- Raised a $10M Series A led by Madrona with General Catalyst, Bloomberg Beta, Operator Partners, and Secure Octane
- Grew revenue from $0 to $1M within 12 months after the pivot
- Reduced client phishing failure rates from roughly 20% to 6%
- Landed enterprise customers including Disney, Pfizer, Thomson Reuters, and MassMutual - many via cold outbound

## Latest updates

- **2025-02** — Rebranded from Cipher to Anagram and announced a $10M Series A led by Madrona.
- **2025-07** — Featured on the Telecom Reseller podcast discussing behavior-based security learning.

## Links

- Website: https://anagramsecurity.com
- LinkedIn: http://www.linkedin.com/in/harleysugarman
- YouTube: https://www.youtube.com/watch?v=BavEOVdkCow

---

Profile page: https://yespress.io/harley-sugarman
Published by YesPress — https://yespress.io
Last updated: 2026-06-04