Ashley Rose

The Story

The person at the keyboard is not the problem. Ignoring them is.

Walk into most cybersecurity companies and you will hear a familiar phrase: the human is the weakest link. Ashley Rose has built a company, and a category, around disagreeing with it. Her argument is not sentimental. It is operational. Most people, she says, show up wanting to do the right thing. They just need context, support, and a nudge at the right moment. Blame them and you learn nothing. Measure them and you can change the odds.

Today Rose is co-founder and CEO of Living Security, the Austin company that helped coin and define Human Risk Management, or HRM. The pitch is deceptively simple. Enterprises pour money into firewalls, endpoint tools, and threat detection, then hand employees a once-a-year compliance video and hope for the best. Living Security reads the behavioral data instead: who clicks, who reports, who reuses passwords, who ignores the policy. It turns that into a risk score, then guides the fix before an incident happens. The workforce stops being a liability line and becomes something you can actually manage.

It began as a physical room

Living Security did not start as software. It started as a puzzle. Her husband and co-founder Drew Rose had been experimenting with gamified security education: card games, and then a Cyber Escape Room where employees solved puzzles tied to real security best practices. Instead of a slide deck about phishing, you got locked in a room and had to think like an attacker to get out. People remembered it. They talked about it. It was, in the most literal sense, engaging, the exact thing traditional awareness training was not.

Rose saw the opening. She had spent years as a product owner on a software team at American Campus Communities, sitting at the intersection of engineering, compliance, operations, and business, watching how enterprise workflows actually broke down and where the human element mattered most. She and Drew launched Living Security out of their Austin house in 2017. After running the early escape-room programs and landing enterprise customers late that year, she left her full-time job. By 2018 she was CEO full-time.

From a beach idea to the Fortune 500

The escape room was not her first product. Her first was swimwear. As a young mom, Rose realized her daughter's swimsuit would be far easier to change if it could simply snap off. She turned that observation into Bella Bare Wear, a line of snap-change kids' swimwear, and raised more than $21,000 on Kickstarter to make it real. The throughline from a snap-off swimsuit to an enterprise cybersecurity platform is not the market. It is the instinct. As she puts it, she has always loved solving problems and making other people's lives a little easier. One version of that instinct fixes a swimsuit. Another fixes the way global companies think about risk.

That instinct scaled. Living Security raised a $5 million Series A in 2020 led by Silverton Partners, then a $14 million Series B in 2021 led by Updata Partners, more than $28 million in total. The money moved the company beyond training into full Human Risk Management and its Unify platform. The client list reads like a directory of institutions you already trust with your money and your health: Mastercard, Verizon, CVS Health, JPMorgan, HP, Target. More than 130 enterprises in all.

Then the machines showed up

In 2025 Living Security launched an AI-native HRM platform built on years of proprietary behavioral data. At its center is Livvy, an always-on intelligence engine that analyzes more than 300 behavioral, identity, and threat signals to flag workforce risk, explain why it matters, and guide remediation before an incident occurs. The company also did something few in the space had: it extended the risk framework to cover AI agents as well as people. If an autonomous agent now sits inside your workforce with access and permissions, Rose's argument is that it is a new kind of insider, and it deserves the same scrutiny as the human two desks over.

The recognition followed the work. In 2024 Rose received a first-time founder award from the Austin Technology Council, at a ceremony that included Michael Dell, and was named to Cybersecurity Ventures' List of Industry Experts. Living Security was named a Leader in The Forrester Wave for Human Risk Management. For a category that barely existed when she and Drew were building puzzle rooms, that is a fast climb.

The philosophy underneath

Rose describes herself as a product-obsessed entrepreneur, and the phrase is doing real work. Her design principle is that systems should guide good decisions through data, AI, and empathy rather than fear. Punishing an employee for clicking a bad link teaches them to hide the click. Giving them a timely, specific, low-friction path to do better teaches them to report it. One approach produces silence. The other produces signal. In a field that has spent two decades scolding users, that is close to heresy, and it is exactly why it works.

Ask her for the single hardest lesson of building a company, mostly bootstrapped in instinct and married to her co-founder, and the answer is not a growth tactic. It is a temperament. The value of resilience, she says. It is an unglamorous answer from someone who has made a career out of turning unglamorous problems, the swimsuit, the compliance video, the ignored security policy, into things people actually want to use.