OPERATORS How to Make AI Work for Your Brand With Two (Enterprise) Insiders
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Mar 4, 2026 Matt Kruer, CIO at Bissell who oversees finance and IT, and Craig Foldes, founder of ChatWalrus and former Global Head of AI at Crocs, discuss making AI practical in large companies. They talk about why most pilots fail, how to find and enable the 10% power users, simple rollout tactics like demos and prompt libraries, and where AI truly earns its keep in CX, marketing, and product.
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Living Through Dozens Of Failed AI Pilots
- Craig ran ~40–50 AI pilots at Crocs and experienced why the oft-cited 95% pilot failure rate is real.
- He spoke with ~200 AI startups and learned many pilots fail from poor fit, execution, or being obsolete once major models add the feature.
Teach One Familiar Tool First For Wide Adoption
- Do drive broad adoption by teaching everyone one familiar tool first, like ChatGPT, before layering in Claude or Gemini.
- Get people comfortable with an 'aha moment' via enablement, then add specialized models for specific strengths.
Require Training And Surface Role Specific Opportunities
- Do require training and surface employee ideas by surveying where AI could help each role.
- Use those responses to pick top departmental opportunities and show measurable impact, creating visible wins.