I'm Ashley Rose.

The short version

I’m the CEO and co-founder of Living Security. We help Global 2000 companies secure their largest attack surface and their greatest asset, their people. I started the company with my husband Drew in 2017, out of the bonus room in our house. I raised a seed round, a Series A and a Series B as a first-time founder, in cybersecurity, as a woman. We raised three daughters during the same nine years. I love to travel, I love a good bottle of wine, and I have never been able to leave a good idea alone.

Drew

I have known Drew since I was 18. He spent years in the military and then a decade in IT and security, on the customer side of the table. He noticed that the security awareness products on the market were built to check a compliance box. They didn’t change behavior and they didn’t reduce risk. He had spoken at security conferences, and everyone he talked to told him the same thing.

When we wrote our first pitch in 2017, we described our partnership in one line: Drew is the vision and Ashley is the focus. He brought the cyber and teaching background. I brought marketing and product. We had been together twelve years and married ten by then, and we said in that first pitch that the relationship had taught us communication, empathy and problem resolution the hard way.

Investors noticed. We heard early that some of them were wary of married founders. One angel chose us because of our marriage. I have come to think being married is more of an asset than a risk. We have disagreed in every way two co-founders can, and we are still married, still business partners, and still each other’s first call.

Drew leads more than Living Security now. He founded Dripping Springs Sports Club, DSSC, a fitness, wellness and sports hub in our hometown, and he directs DS Elite Volleyball, a girls club volleyball program that trains at DSSC. Both are ours, and both are in the town where we live and raise our girls. Drew and I are each on our own AI journey, and we each run more than one company. We inspire and support each other, and he is still my first call.

The bonus room

Living Security started as in-person escape rooms that taught security awareness. We turned the bonus room of our house into a 500-square-foot headquarters. At one point seven of us worked in that room. I left my full-time job in late 2017 and was all in as CEO by early 2018.

Before that, I had studied business at the University of Michigan, worked on a software team at American Campus Communities, and launched a kids’ swimwear line on Kickstarter. I had never run a cybersecurity company, and I wasn’t going to wait until I had.

We started out of Capital Factory’s orbit, and Capital Factory later invested in our seed round. We chose Austin for the innovation ecosystem around the University of Texas. I have since judged many pitch competitions at UT myself, because someone did it for us.

Raising money as a first-time founder

We closed our seed round in November 2018, led by Active Capital. We raised a Series A in 2020, led by Silverton Partners, and a Series B in 2021, led by Updata Partners. I did all of it as a first-time founder in a field dominated by men.

I wrote at the time that the biggest battle I faced was with myself. A founder who is also a woman in cyber walks into a lot of rooms where nobody looks like her. I learned to do the homework, tell the story plainly, and let the customer results do the talking. The Austin Technology Council gave me its First-Time Founder Award in 2024, and I accepted it for everyone who walked into those rooms with me.

What we built

We started with escape rooms. We moved to a digital platform with CyberEscape Online and Unify, and in 2025 we rebuilt the company as an AI-native platform. Along the way we pioneered the category called Human Risk Management. Forrester named us a Leader in its Human Risk Management Wave. Global 2000 companies in healthcare, financial services and retail rely on us to see and reduce the risk that comes from their people.

I believe people are the largest attack surface in every company, and they are also the greatest asset a company has. The goal is to protect 100 million users.

HRMCon

HRMCon is the conference we built for the category we created. It started as a way to put the best CISOs, analysts and practitioners in one room and let them argue about what works. In 2021, it drew more than 1,500 attendees. On October 20, 2025, we used HRMCon to launch our AI-native platform, with a live audience at Q2 Stadium in Austin and hundreds more online. The room was full of the people who had been with us since the escape room days.

The team

The team did the hard part. Our engineering, product and AI leaders turned a prototype into a platform. Our sales, partner, support, marketing and customer success leaders took it to the companies that rely on it.

I have never run a company alone and I wouldn’t want to. When our engineers went from specs to agentic loops in a matter of months, I watched a small team change how software gets made.

Three girls, nine years

When we founded Living Security, our daughters were in preschool and grade school. We raised our kids and built the company at the same time. Our weekends are tournaments, practices and drives to Austin. The company grew up beside them.

I lead Kardivas for Dripping Springs ISD, a character mentorship program for fifth-grade girls, which I brought to our district by partnering with the founder who has run it for over 20 years. Our girls are why I started it, and the work gives me as much as it gives them.

Travel and wine

I love to travel and I love experiences more than things. I also love wine. I have hosted tastings and dinners for friends, customers and my EO group. A good dinner with a good bottle is how I think best, and it’s where some of my best friendships started.

Where to find me

Dripping Springs, Texas. I host Security, Sold, a podcast for CISOs. I speak at EWF, the security ISACs, CSI and IASAP, write for Forbes, and advise the NCA. I am part of EO Austin and the EMP Class of 2026.