Iterating Toward Better Search: A Two-Agent Simulation Framework for Evaluating Agentic Search Architectures in E-Commerce

We present a modular two-agent simulation framework for evaluating conversational shopping assistant architectures. An independent buyer agent, configured with personas, missions, and patience levels, is paired with an interchangeable responder that integrates with a real e-commerce search API. Holding the buyer constant across experiments enables controlled comparison of responder designs on identical scenarios. Using 2011 conversations across 14 persona buckets, we establish four empirical findings. First, rolling-window memory outperforms intent-extraction memory on all quality metrics while being 35% faster per query. Second, illustrating rapid evidence-driven iteration, a systematic failure analysis of a responder version enables targeted fixes that reduce failure and near-failure rates by 62% across the full dataset. Third, swapping the responder LLM backbone from Gemini~2.5 to Llama~3.3~70B costs 0.16--0.45 points despite identical architecture. Finally, we document systematic philosophical disagreement between frontier LLM judges: Gemini rewards process correctness while Claude demands concrete outcomes, despite using the same evaluation prompt.

A Chain-of-Thought Approach to Semantic Query Categorization in e-Commerce Taxonomies

Search in e-Commerce is powered at the core by a structured representation of the inventory, often formulated as a category taxonomy. An important capability in e-Commerce with hierarchical taxonomies is to select a set of relevant leaf categories that are semantically aligned with a given user query. In this scope, we address a fundamental problem of search query categorization in real-world e-Commerce taxonomies. A correct categorization of a query not only provides a way to zoom into the correct inventory space, but opens the door to multiple intent understanding capabilities for a query. A practical and accurate solution to this problem has many applications in e-commerce, including constraining retrieved items and improving the relevance of the search results. For this task, we explore a novel Chain-of-Thought (CoT) paradigm that combines simple tree-search with LLM semantic scoring. Assessing its classification performance on human-judged query-category pairs, relevance tests, and LLM-based reference methods, we find that the CoT approach performs better than a benchmark that uses embedding-based query category predictions. We show how the CoT approach can detect problems within a hierarchical taxonomy. Finally, we also propose LLM-based approaches for query-categorization of the same spirit, but which scale better at the range of millions of queries.