Open to opportunities

Akil Simmons

@akilsimmons

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Enterprise AI transformation leader delivering secure, scalable AI solutions and programs.

United States

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What I'm looking for

I’m looking to lead enterprise AI strategy and delivery—governing generative AI, modernizing workflows, and ensuring secure RMF/NIST/FedRAMP-ready implementations with cross-functional teams.

I’m an enterprise technology executive with 20+ years of experience leading AI transformation, digital modernization, cybersecurity, and enterprise technology initiatives across government and commercial organizations.

As the Founder of Calculated Ventures, LLC, I advise executives on enterprise AI strategy, AI adoption, governance, and modernization, with a strong focus on workflow automation and secure technology delivery. I design AI-enabled workflows for proposals, documentation, research, reporting, and knowledge management.

I bridge executive strategy with technical execution by leading cross-functional teams and enterprise modernization initiatives. I’ve also developed the CalculatedIT RMF Automation Platform concept and created the Vulcan Analytics AI-enabled infrastructure intelligence concept.

Experience

Work history, roles, and key accomplishments

Current

Founder & Principal AI Consultant

Current

Calculated Ventures, LLC

Jan 2008 - Present (18 years 6 months)

Advise executives on enterprise AI strategy, AI adoption, governance, and digital modernization. Design AI-enabled workflows for knowledge management and proposals, and developed concepts for RMF automation and AI-enabled infrastructure intelligence.