A system and method for automated multi-channel customer journey testing, that links communication channels and follows a customer interaction across multiple channels as a single journey, incorporating data and interaction content from each channel utilized to maintain a “big picture” view of a customer's journey across these channels during an interaction. The invention also provides flexible success indicators to accommodate virtual assistant and chat bot programs, by accommodating variances in expected test results such as to handle natural language variance, time of day, context, and other factors that may cause variances in interaction content.