I’m Charles B. Holmes IV, a Chicago-based digital marketing leader and operator focused on growth systems, operational execution, and long-term value creation. I work at the intersection of digital marketing strategy, AI-enabled systems, and business operations, helping teams turn complexity into measurable and repeatable outcomes.

My foundation is in performance marketing and analytics, where I have led campaign optimization initiatives, improved return on investment through data-driven decision making, and built scalable processes that support sustainable growth. Over time, that work expanded into automation and applied AI, using modern tools to streamline workflows, improve reporting accuracy, and strengthen operational consistency.

In addition to growth and marketing execution, I have experience working in structured procurement environments that involve federal, state, county, and city stakeholders. Operating within these frameworks shaped how I approach documentation, compliance standards, risk management, and multi-stakeholder coordination. I prioritize clarity, accountability, and systems that hold up under review.

Beyond marketing and operations, I maintain a long-term focus on business ownership, real estate, and disciplined acquisition strategy. I am drawn to established businesses with strong fundamentals where thoughtful systems, strategic execution, and financial discipline can compound value over time.

Why Work With Me?

• Digital Marketing Strategy: Experience leading performance initiatives across paid media, analytics, and conversion optimization with measurable impact.
• Systems and Operations: I design repeatable processes that reduce inefficiency and improve long-term scalability.
• Applied AI Implementation: I integrate AI into marketing and operational workflows in practical ways that support real business objectives.
• Procurement and Compliance Experience: Comfortable navigating structured requirements across federal, state, county, and city environments.
• Long-Term Value Orientation: Focused on durable advantages that compound operationally, financially, and strategically.

If you are looking for a strategic partner in Chicago who combines marketing expertise, operational discipline, and a long-term ownership mindset, I would welcome the opportunity to connect.