security-awareness-training
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Ashley Rose
Ashley Rose is the co-founder and CEO of Living Security, the Austin-based company that turned dull compliance-checkbox security training into a data-driven discipline it helped name: Human Risk Management. She built the company in 2017 with her husband Drew, starting with in-person cyber escape rooms and scaling into an AI-native platform used by enterprises like Mastercard, Verizon, CVS Health and JPMorgan. A product-obsessed entrepreneur who once funded a kids' snap-change swimwear line on Kickstarter, Rose argues the industry has the human problem backwards: people are not the weakest link, they are the largest attack surface worth investing in.
Upfort
Upfort (formerly Paladin Cyber) is a San Francisco-based platform that unifies turnkey cybersecurity with cyber insurance, making cyber risk easy to manage and simple to insure for small and medium-sized businesses. Its Upfort Shield suite layers AI-driven email and web protection, risk monitoring, and security awareness training, while its insurance arm partners with leading carriers to embed coverage for ransomware, wire fraud, and data breaches - sold through brokers and MGAs rather than direct.
Proofpoint
Proofpoint is a cybersecurity and compliance company that protects organizations against the threats that target people - email attacks, data loss, and insider risk. Founded in 2002, it became the first SaaS-based cybersecurity vendor to cross $1B in annual revenue, was taken private by Thoma Bravo for $12.3B in 2021, and today runs a 'human-centric' security platform spanning email defense, data security, and identity threat protection used by a majority of the Fortune 100.
Huntress
Huntress is a Maryland-based managed cybersecurity company that brings enterprise-grade protection to small and mid-sized businesses and the IT providers who serve them. Founded in 2015 by three former NSA cyber operators, it pairs lightweight software agents with a 24/7 human-led, AI-assisted Security Operations Center to detect, investigate, and remediate threats across endpoints, identities, Microsoft 365, and logs. What began with $100,000 in DEF CON Capture the Flag winnings has grown into a cybersecurity unicorn protecting roughly 150,000 businesses and surpassing $100M in annual recurring revenue.
Jericho Security
Jericho Security is a New York-based cybersecurity company that uses generative AI to defend organizations against AI-powered attacks. Its platform runs hyper-realistic, AI-generated phishing, voice-clone, and deepfake simulations to train employees, then measures human risk through a dashboard of analytics and KPIs. Founded in 2023, the company pits an AI 'red team' against an AI 'blue team' to find and close the gaps attackers now exploit at machine speed - an approach it sums up as fighting AI with AI.
Trustifi
Trustifi is a cloud-based, AI-driven email security company that protects organizations from phishing, business email compromise, data leaks and compliance failures. Its one-stack platform pairs Inbound Shield threat detection with Outbound Shield one-click encryption and One-Click Compliance, making enterprise-grade email protection simple enough for small businesses and the managed service providers that serve them. Founded by Rom Hendler and Idan Udi Edry, the company raised a $25M Series A in 2025 to scale its channel-first, AI-powered platform.
Living Security
Living Security is an Austin-based cybersecurity company that pioneered Human Risk Management (HRM), moving organizations beyond check-the-box compliance training toward measurable behavior change. Its AI-native Unify platform correlates behavioral, identity, and threat signals to find the small share of employees who drive most of an organization's risk, then guides targeted interventions. Founded in 2017 by Ashley and Drew Rose, the company serves more than 100 enterprises including Fortune 500 names, and was named a Leader in the 2024 Forrester Wave for Human Risk Management Solutions.
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.
Sage Wohns
Sage Wohns is the CEO and Co-Founder of Jericho Security, a New York-based AI cybersecurity company that trains humans and AI systems to defend against AI-powered attacks including hyper-realistic phishing, deepfakes, and voice cloning. A Seattle native and 10-year AI industry veteran, Wohns previously built and led Agolo, a Google- and Microsoft-backed NLP summarization company, before co-founding Jericho Security in 2023. The company made history by winning the Pentagon's first-ever generative AI defense contract through AFWERX in December 2023, and has since raised $18M in total funding, including a $15M Series A in April 2025. With 39 employees and 30+ enterprise clients, Jericho Security is at the frontier of AI-versus-AI cyber defense.
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.