45 Questions for B2B Commerce AI Evaluations

Built Around the Questions
Vendors Hope You Don't Ask
Know exactly which AI you're evaluating
Generative models, predictive ML, semantic search, and agentic systems carry different risk profiles and require different questions. The checklist maps each commerce capability to the AI type powering it so you know which sections apply to what’s being demonstrated.
Nine areas, including the ones standard RFPs miss
Permission inheritance, guardrail architecture, and transactional reliability are covered. So are consumption billing models, secondary platform costs, and data exit terms – the questions most buying teams only encounter after they’ve signed.
A question that requires escalation is itself a signal
Vendors shipping production-grade AI can answer questions about data governance, permission enforcement, and failure modes in the room. Note which questions get escalated. The pattern tells you as much as the answers do.