Meet the Team

Cloud Underground is made up of a small, yet well-rounded, team of innovative and passionate engineers and entrepreneurs. We do what we do for the Cloud Underground because we love it.

Nato Riley, CEO

Nato Riley is a serial entrepreneur, data scientist, and angel investor with over 10 years of experience in security, disaster recovery, and artificial intelligence. He is the Chief Financial Officer of Cloud Underground, a platform engineering and DevSecOps venture capital firm that enables innovative technology startups to launch and scale.

As a CFO, Nato is responsible for making final financial decisions, driving funding goals and initiatives, and planning revenue and profit strategies. He also leverages his data science and cybersecurity skills to teach online courses on LinkedIn Learning and run a YouTube channel called Nato as Code. Nato holds several certifications, and studied communications and business at Western Colorado University. Nato is passionate about helping leaders achieve complex and costly technology outcomes, and inspiring others to overcome challenges and pursue their dreams.

Find Nato on LinkedIn.

Subscribe to Nato as Code on YouTube.

Randall Massie, CISO

Randall is a Cyber Defense Security Engineer with more than 20 years of experience in IT and software development. He is a U.S. Coast Guard veteran and has spent most of his civilian career in the enterprise fintech space. He is passionate about learning and innovating new technologies, which led him to cloud engineering and DevSecOps.

When he isn’t deep in code or defending against cyber-attacks, he is spending quality family time with his wife and four beautiful children.

Find Randall on LinkedIn.

Ken Underhill, Underground Ops Chief Strategy Officer | CEO of Underground Ops

Ken is a Co-founder at Cyber Life, which helps train senior leadership teams on cybersecurity as a business risk. He is also an international best selling author and multi-award winning cybersecurity professional. Ken sits on the board for several cybersecurity women's organizations and he has educated over a million people around the world.

Find Ken on LinkedIn.

Subscribe to CyberLife on YouTube.

Learn more about CyberLife TV.