Ep 16: Lori Crooks: Cybersecurity, Compliance, and the Realities of Entrepreneurship

In this episode of Dear Tech, we sit down with Lori Crooks, Founder and CEO of Cadra, a cybersecurity consultancy on a mission to make compliance approachable for businesses of all sizes. Lori brings over 20 years of experience in IT auditing, security frameworks, and technical documentation — but her journey didn’t start in tech. We dive into her path from finance to IT auditing, what inspired her to leave the corporate world, and the unexpected challenges of entrepreneurship.We explore:Why she walked away from corporate life and how she built Cadra from the ground upWhat makes cybersecurity compliance so misunderstood (and often neglected)Surprising gaps in how small businesses think about IT and securityThe importance of making technical work human and understandableFedRAMP, NIST, CMMC, and the real-world impact of regulatory frameworksWhat AI means for cybersecurity compliance — and what’s coming nextThe human side of leadership, working remote, and managing a values-driven teamHer mentorship philosophy, favorite client wins, and… the time she met a hard drive that had been shot with a bulletPlus, we talk dogs, Harry Potter houses, and why “you are good enough” is the sticky note she’d leave for her past self — and maybe for all of us.🎧 Listen now and don’t forget to follow the show.🔗 Learn more about Lori’s work: www.cadra.com📲 Connect with Lori on LinkedIn: https://www.linkedin.com/in/lori-crooks