CW Strategies

CW Strategies works with organizations that are scaling faster than their systems can handle. Teams are siloed instead of shipping. Leadership is stretched. The mission is clear but the operations aren't keeping up.

Derek builds the infrastructure that lets visionary leaders focus externally while the organization scales sustainably. Then he transfers ownership and gets out of the way.

CW Strategies is AI-native. Derek doesn't advise on AI from a distance — he builds with it every day. Same discipline he used leading 55-person newsroom teams, now running through AI: morning standup, work the plan, hand off clean at night.

Documentation-first. Reusable workflows. Systems that keep working after the engagement ends. The material changed. The work ethic didn't.

• Mission-driven organizations ($2M–$10M revenue)
• Leaders in growth or transition who need operational leadership, not another consultant with a slide deck
• Nonprofits, media companies, and organizations navigating AI adoption or digital transformation
• Founders and executives who want strategic challenge, not yes-men

Every engagement is different. Some organizations need embedded leadership. Some need a defined build with a clean exit. Derek does both.

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