What We Did

We started with an audit of the current state of Crestline and AI using the SPDR framework (strategy, processes, data, and resources) — all four systems assessed simultaneously. This is often called the AI readiness assessment. For Crestline, that audit revealed that business strategy needed to come first. AI is only as useful as the context it operates in, and Crestline didn't yet have a documented strategy to give it that context. So we built the strategy first. AI can accelerate this, but it was a choice not to involve at this stage.

Once the foundation existed, the AI engagement had something real to work with. The approach was Human-Led AI from day one: give the whole team access to a frontier model, establish governance and a starter prompt library, and run a 60-90 day organic pilot with no mandated use cases. Let the team discover what's useful. Document what emerges. Let that drive what comes next.

What came out of that was a complete AI strategy: tool selection rationale, governance framework, training and onboarding structure, a NotebookLM hub housing the prompt library, best practices, and use case library. And, an honest picture of what Phase 2 looks like if the pilot succeeds, and what it means if it doesn't.