Kyle Cain

About Me

I started my IT career from the ground up, cutting my teeth on the helpdesk before moving deep into systems and cloud engineering. Over the years—from my time at COLSA Corporation to my current role at Workstreet—I realized that building a scalable cloud environment is only half the battle. Ensuring infrastructure is genuinely secure, resilient, and compliant is the challenge that really drew me in. That realization naturally bridged the gap between my engineering roots and the complex world of GRC. Ultimately, my main goal, whether it's my business or not, is to always make organizations inherently more efficient, effective, and profitable.

Coming from a family of lawyers by both blood and marriage, I’ve always had an inherent knack for parsing through dense legalese. Today, I use that to operate at the framework level, dealing with heavy-hitters like CMMC, NIST 800-53, and ISO 27001. One of my biggest strengths is taking the notoriously vague language of these regulations and translating it into clear, actionable steps for other engineers. It’s about bridging the communication gap so that technical teams understand exactly how to apply those requirements and build security directly into the infrastructure from day one.

Lately, my focus has been helping companies in the Defense Industrial Base (DIB) navigate the massive undertaking of CMMC and NIST 800-171. I help organizations understand what it actually means to be compliant with 800-171A in practice. It goes beyond just reading the controls on paper; it's about understanding the nuance, governing exactly how to process, store, and transmit FCI and CUI, and ensuring that the evidence collected is both adequate and sufficient to meet any assessment objective. I love taking a company from absolute zero to a full 110 by automating those manual bottlenecks and turning a massive compliance headache into a streamlined operational advantage.

Experience Highlights

• Led previous employer to CMMC L2 ISO 27001:2022 certifications
• Migrated multiple organizational platforms/processes to more automated solutions and/or platforms across sovereign/government clouds
• Reduced overall costs on those ^^ projects by over $150k/year and reduced operational overhead by over 50%
• Building out GRC tools/platforms as well as integrating/bringing together open source tools to
• create well-rounded solutions for business impact/efficiency

Get in Touch

Always open to chatting about CMMC and other federal compliance frameworks/initiatives, compliance engineering/automation, or new, bleeding-edge news/tools applicable to the world of CMMC, FedRAMP, or GRC on the whole.