Living Security

Ashley Rose and her husband Drew co-founded Living Security in mid-2017, launching officially in October of that year. They identified a gap in how enterprises approached cybersecurity training—it was often checkbox compliance work that employees found boring and ineffective. Ashley wanted to build something that would help companies develop positive security cultures by making awareness training engaging and quantifiable.

The team started with an escape room concept: immersive, in-person cybersecurity training experiences that were completely novel in the market. Rather than cannibalizing this with a pure SaaS product, they built a complementary online platform to scale what worked. By 2019, they had three-quarters of revenue coming from the SaaS application itself, with the remainder split between escape room licensing (recurring platform revenue) and professional services (hosted escape room events). This hybrid approach proved remarkably sticky.

Living Security targeted Fortune 1000 enterprises and landed their first customers through a mixed acquisition model. By 2020, about 50% of new customer signups were coming directly from their website through an effective lead magnet: a free cybersecurity card game (costing $5-7 to produce) that generated 20-25% email capture rates. The remaining growth came from direct sales and regional cybersecurity events like RMISC (Rocky Mountain Information Security Conference), where they would demo their escape room experience. Their CAC payback was remarkably efficient at around 6 months on a $24K average annual contract value.

The escape room concept was supposed to be a temporary onboarding tool, but the market loved it. Rather than killing it as VCs suggested, Ashley doubled down on the upsell dynamics it created. One escape room event would lead to platform adoption, which led to expansion within the account. This upsell engine was the real story: with 1% annual gross revenue churn and over 300% net revenue retention (later clarified as mid-300s to 400%), the company achieved unit economics most SaaS companies only dream of. Their larger platform customers paid six figures annually. The direct sales model scaled efficiently too—their first quota-carrying rep was expected to close north of $500K in new ARR, and their newly hired VP of Sales was tasked with building out the team using the same playbook.

By early 2020, Living Security had grown to 18 people, 58 customers, and was burning less than $10K per month despite aggressive hiring. They had two quota-carrying sales reps plus a new VP of Sales, and were raising a Series A targeting $5-8 million at a valuation north of 10X revenue multiple (over $13.8M pre-money). Ashley expressed confidence in their 2020 trajectory, noting they were already exceeding Q1 goals by mid-January. The business had proved that an unusual hybrid model could deliver enterprise-grade growth metrics and unit economics.