Exit Stories: Security Journey’s Chris Romeo Talks HackEDU Acquisition

Image | Jackie Sizing

Prompted by Exit Stories host Kevin Mosley, Security Journey Founder Chris Romeo walks listeners through the company’s journey—see what we did there?—through its May 2022 acquisition by HackEDU. 

Founded in 2015 with his wife Deborah after Romeo developed a successful cybersecurity training program for his former employer Cisco, the duo bootstrapped slowly but steadily into an industry leader. Today, Romeo works as Chief Strategy and Security Officer at post-acquisition Security Journey. [Editor’s Note: We first wrote about Raleigh-based Security Journey and the acquisition in July.] When Romeo isn’t working you can catch him in Fuquay-Varina or on his “AppSec” podcast. 

Here are three key takeaways from this week’s episode of Exit Stories: 

  • Don’t be afraid to give away your knowledge for free. Romeo is well aware this may be a controversial take, but as an early-stage founder he got in the ears of potential customers by speaking on cybersecurity at conferences. He knows he could’ve packaged this knowledge as a product, but to Romeo, establishing himself as an expert in the field was more valuable. “​​I’ve given away a lot of knowledge and a lot of information over the years of being a part of Security Journey, and all it’s done is caused people to look at us and go, ‘Oh, those people know what they’re talking about,’” Romeo said. (16:00) 
  • When marketing budgets are slim, establish yourself through coffee meetings and LinkedIn conversations. With just one sales rep, Romeo braved 26 coffee meetings at the first RSA conference he attended as Security Journey’s founder. Not all of those meetings turned into customers—but the ones that did turned into really great customers. Romeo also recommends LinkedIn’s Sales Navigator as an excellent value for early-stage startups. (17:30, 20:18)  
  • First-time founders, learn when to take off one of your many hats. When Romeo left Cisco to start Security Journey, it was just himself and his wife on the team. But as the team grew, he had trouble giving away the many responsibilities he had taken on over the years. Romeo recommends the “Swimlane” process flow diagrams for deciding how to portion off responsibilities. (31:33) 

You can listen to the full episode below. Be sure to subscribe so you’re notified of each new episode.