Build, Judge, Optimize: A Blueprint for Continuous Improvement of Multi-Agent Consumer Assistants

We present a framework for evaluating and improving a large-scale, multi-agent shopping assistant in production, and report lessons from its use. Offline evaluation of such a system faces three obstacles. (i) A logged conversation cannot be replayed against a modified system, because a different response changes every turn that follows. (ii) The unchanged system itself varies from run to run. Its LLM components are stochastic, and in product search the available products, their prices, and the customer's personalization signals change. (iii) Aggregate quality scores combine distinct behaviors, so they show that quality has changed but not which behavior caused the change. Our framework addresses each obstacle in turn. For a reported behavior, an Evaluation Harness generates targeted assertions and a fixed cohort of customer scenarios. It then reproduces the behavior in a local instance of the assistant through grounded user simulation. Instead of replaying the log, the simulator writes new customer turns conditioned on the recorded messages and context. Repeated runs of the unchanged system form a stored baseline. An Improvement Orchestrator turns the assertion results into hypotheses, implements each as an isolated modification, and compares it with the baseline using paired percentile bootstrap intervals over scenario-level differences. When an investigation ends, the harness may propose revisions to future evaluations, subject to human approval and without altering past decisions. We report production investigations with this framework. Assertion profiles showed which positions of a product carousel a failure affected, and repeated runs distinguished a real improvement from run-to-run fluctuation. Audits of the evaluation itself found a judge that lacked the evidence it needed and a model setting that was configured but not applied.

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 Gemini2.5 to Llama3.3~70B 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.

Conversational shopping assistants now serve hundreds of millions of customers, yet no existing benchmark jointly evaluates the open-ended multi-turn reasoning, domain expertise, and criterion-level quality that real shopping conversations demand. Shopping reasoning is unique among language model applications. Unlike factual question answering or verifiable code generation, it requires balancing subjective preferences, budget constraints, and cross-product trade-offs across multi-turn dialogue, capabilities absent from previous e-commerce and general-purpose benchmarks. We introduce the Shopping Reasoning Bench, an expert-authored benchmark of 525 missions (232 single-turn, 293 multi-turn) with 10863 importance-weighted binary rubrics authored by retail domain experts. These criteria are organized under a taxonomy of five reasoning categories and fifteen subcategories covering diverse demands such as preference refinement, trade-off analysis, and compatibility assessment. An evaluation of nine models across three families (GPT, Claude, Gemini) shows that pass rates reach only 57--77% overall. On multi-turn missions, all models score 13--29 points lower on optional above-and-beyond criteria than on required ones, and performance degrades 4--18 points as conversations progress. These gaps show that current models handle basic shopping assistance but fall short of expert-level advice, making Shopping Reasoning Bench a challenging testbed for future shopping assistant development.