Charles Holmes I.V.

AI Strategy. Growth Systems. Long-Term Value.

I build practical AI and marketing systems that help businesses operate smarter, grow predictably, and create durable long-term value.

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OPERATOR MINDSET. CHICAGO ROOTS

I operate at the intersection of AI strategy, growth systems, and execution. My background spans digital marketing, automation, and business operations — inside established organizations and across my own ventures.

I focus on building systems that create leverage, not short-term wins. The goal is simple: design durable advantages that compound over time.

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FROM THE BLOG

AI resume optimization workflow improving match score and ATS performanceAI
02/25/2026

The 3 ChatGPT Resume Prompts That Helped Me Compete for $100K+ Roles

Most resumes do not fail because you are unqualified. They fail because they do not match the job description. They do not prove measurable impact. And they get filtered out…
Charles
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Small business operations dashboard in a real service workspaceAI
02/22/2026

AI Isn’t Magic. It’s Margin.

The Problem With How People Talk About AI If you listen to headlines, AI sounds like magic. It is either going to replace your team or transform your company overnight.…
Charles
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Business
08/01/2020

The Proven Six Benefits Of Growing Your Business With Facebook Messenger Chatbots

In this age of automation, chatbots are a big thing. And with advances in technology, it is vital for you to step up your game. Scaling your business is easy…
Charles
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