Conversational Recommender Systems (CRSs) aim to engage users in dialogue to provide tailored recommendations. While traditional CRSs focus on eliciting preferences and retrieving items, real-world e-commerce interactions involve more complex decision-making, where users consider multiple factors beyond simple attributes. To capture this complexity, we introduce Conversational Sales (CSALES), a novel task that integrates preference elicitation, recommendation, and persuasion within a unified conversational framework. To support realistic and systematic evaluation, we present CSUSER, an evaluation protocol with LLM-based user simulator grounded in real-world behavioral data by modeling fine-grained user profiles for personalized interaction. We also propose CSI, a conversational sales agent that proactively infers contextual user profiles and strategically selects actions through conversation. Comprehensive experiments show that CSI significantly improves both recommendation success and persuasive effectiveness across diverse user profiles.

Recent developments in Conversational Recommender Systems (CRSs) have focused on simulating real-world interactions between users and CRSs to create more realistic evaluation environments. Despite considerable advancements, reliably assessing the capability of CRSs in eliciting user preferences remains a significant challenge. We observe that user-CRS interactions in existing evaluation protocols resemble a guessing game, as they construct target-biased simulators pre-encoded with target item knowledge, thereby allowing the CRS to shortcut the elicitation process. Moreover, we reveal that current evaluation metrics, which predominantly emphasize single-turn recall of target items, suffer from target ambiguity in multi-turn settings and overlook the intermediate process of preference elicitation. To address these issues, we introduce PEPPER, a novel CRS evaluation protocol with target-free user simulators that enable users to gradually discover their preferences through enriched interactions, along with detailed measures for comprehensively assessing the preference elicitation capabilities of CRSs. Through extensive experiments, we validate PEPPER as a reliable simulation environment and offer a thorough analysis of how effectively current CRSs perform in preference elicitation and recommendation.