Living Security CEO and Co-Founder Ashley Rose on Solving Human Cybersecurity Risk

The Crunchbase “Female Founder Series” is comprised of stories, Q&As and thought-leadership pieces from glass-ceiling-smashers who overcame the odds and are now leading successful companies, or investing in them.

Ashley Rose is the CEO and co-founder of Living Security. Living Security is a human risk management platform that’s moving the needle in enterprise security by effectively changing human behavior and proactively identifying vulnerabilities.

Prior to founding Living Security, Rose worked on a software team at American Campus Communities, where she quickly developed a strong intuition for delivering customer-centric solutions. She and her husband, Drew Rose, realized that amidst growing cybersecurity threats, there was a massive need at enterprises to improve security training and have a way to measure whether they were reducing risks. In 2017, the duo launched Living Security and now have more than 130 enterprise companies leveraging Living Security’s solutions.

In this Q&A, Ashley shares her journey launching a startup, how she raised more than $20 million in under four years, and the biases she faced from investors. 

Ashley Rose, CEO and Co-founder of Living Security.

Q: Did you always know you wanted to be an entrepreneur?

I have always loved solving problems and helping others by making their lives a little easier. I think that’s really what drives my innovative spirit and led me down this path of founding a company. I first dipped my toe into the entrepreneurial pool as a young mom. I was at the beach, trying to wrangle my daughter out of her wet swimsuit so that I could change her diaper. I realized that things would be so much easier if her swimsuit could just simply snap off. 

An idea was born, and I launched Bella Bare Wear, a line of functional, snap-change swimwear for kids that raised more than $21,000 through a Kickstarter campaign. Ninety days later, customers had a finished product in their hands, and my first business was up and running.


Q: What problems were you trying to solve with your company?

The rise of high-profile ransomware attacks during the past year has put cybersecurity at the forefront of mainstream news more often, but the reality is that companies have been investing billions of dollars in this issue for years with little progress. Every company, big and small, remains at risk, and attacks cost enterprises billions of dollars every year. The reason is pretty straightforward: most attacks are linked back to human error, but companies do the bare minimum to educate employees about recognizing and responding to threats. 

Drew and I recognized that traditional security awareness training needed to be revamped for the modern workplace to move the needle of enterprise security. We wanted to create a human risk management platform that genuinely engages employees and takes into account how different people learn. 

Living Security training is based on the idea that gamified learning that’s fun and interactive is more effective. Proper teaching requires showing users how to make better security decisions versus simply telling them. Our hunch was correct, and our platform is proven to be 16 times more effective than traditional training programs.


Q: What is your advice for other female founders at the beginning of their entrepreneurial journeys?

Quite honestly, the biggest battle I faced was with myself. I am a confident and capable person, but starting a new business in a brand new and primarily male-driven industry put me in many situations that left me feeling out of my depth. Every day I had to brush those doubts aside and focus instead on making new connections with people who could help me learn. 

My advice would be to partner and surround yourself with others who are further along in their journeys and are willing to share their knowledge with you while encouraging you as you grow. Additionally, my advice is to block out the negative thoughts and stay intently focused on what drives you to build your business. Finally, it is important to remember that there is a reason why you are in your seat. The experience and skills I brought to this company are what got us to where we are today.


Q: How have you integrated your values and mission into your own company structure?

As a female founder, gender diversity and inclusion are incredibly important to me and I want to see more women joining the tech industry. Currently, 50 percent of the Living Security team are women, and I’m committed to keeping that balance. It’s also a priority to make sure women are continually promoted and offered leadership roles as they open up. 


Q: What do you find most rewarding about your experience as a founder so far?

I enjoy the varying challenges that present themselves on a daily, and sometimes even hourly, basis. I’m a problem solver, and I love learning new things that can immediately impact a customer, partner, or team member. But, most rewarding of all has been building a team of other problem-solvers committed to making a difference every day, both inside and outside the office.


Q: What are the biggest lessons you learned when raising funding? 

My number one lesson would be the value of resilience. You’re going to hear a lot of ‘no’s, but you need to keep pushing forward. Resilience will also help you navigate the many twists and turns that come with growing a startup. 

When we initially launched Living Security, we were offering in-person enterprise security training in the form of on-site escape rooms. We quickly realized that there was a huge market opportunity for us to grow with a digital offering that matched what we were delivering in person. 

However, when we went out to raise, many venture capital investors were skeptical about the concept. We brushed off the doubt because we knew we were building something to meet the needs of our customers directly, and we stayed laser-focused on our vision. In the end, our intuition was correct, and we went on to serve the needs of big enterprises like CVS and AmerisourceBergen with our online platform.


Q: How did you know you were choosing the right investors? What have they brought to the company? 

Across each round of funding, I knew that we needed investors who would truly partner with us to build the company. Our board is comprised of seasoned B2B SaaS and cybersecurity investors who have been in our shoes; they have navigated the challenges of taking a visionary startup and turning it into a successful business. We’ve been lucky to partner with investors who believe in us and our ability to make a difference in this market.


Q: What is it like to co-found a company with your partner?

When we started Living Security, Drew and I faced an immediate roadblock as we met with investors. Most people wouldn’t come right out and say it, but we knew there was definitely a bias against investing in a company where the founders are a married couple. 

I get it; it’s risky. What if the marriage falls apart and that discord impacts the business? We’ve had to brush that bias aside and push forward. Ironically enough, one of our first angel investors chose us specifically because of our marriage. He spent time with us and our three children and saw the great dynamic we have with one another.

Ultimately, we’ve found that being married is more of an asset than a risk. Our partnership as spouses and co-founders has directly led to a great deal of our success so far. We know each other’s strengths and weaknesses and use that awareness for the company’s benefit. 

  • Originally published November 15, 2021, updated April 26, 2023