Taming AI Sprawl: An Evaluation Kit for IT Teams

This kit equips IT leaders with practical tools and frameworks to tame the growing AI sprawl, evaluate your AI stack, and lay the groundwork for AI’s agentic future. Whether you’re consolidating existing tools, proving ROI, or preparing for more autonomous systems, these resources will help you lead with strategy, structure, and confidence.

The CIO Playbook: Proving the ROI of AI

A decision-making framework for CIOs and IT leaders ready to scale what’s working and sunset what isn’t. Learn how to measure value across compliance, quality, adoption, and business impact.

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The AI ROI Scorecard

A downloadable, customizable scorecard for measuring individual tools against compliance, quality, adoption, and business impact.

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The AI Evaluation Matrix for IT Leaders

A customizable spreadsheet designed to help you assess each AI tool’s maturity, integration, and alignment against enterprise priorities. Once complete, it will allow you to quickly identify gaps, overlaps, and opportunities across your stack.

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30 Questions to Ask Any AI Vendor

A vetted set of evaluation questions that go beyond surface-level functionality, covering deployment, security, scalability, and readiness for agentic AI. Designed for IT teams making strategic buying decisions.

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Grammarly’s Enterprise AI Evaluation Snapshot

Grammarly’s answers to all 30 evaluation questions. See how we approach privacy, governance, scalability, and responsible AI—so you can assess our solution with full transparency.

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