Personalization is classically a two-party problem: a sender chooses what to say, and a receiver with independent objectives decides whether to act. A salesperson pitching the same analytics product leads with HIPAA compliance for a hospital and real-time reporting for a retailer, expecting a different argument to work on each. Existing LLM personalization benchmarks measure a narrower, one-party property: whether output matches the preferences of the same user it serves-sender and receiver being the same, as when RLHF aligns an assistant to its own user. The two-party case is harder to study automatically, since it needs ground truth linking specific content to an observed receiver action. Sales outreach provides this: a message written for one prospect, recorded against whether it produced a reply, a call, or a closed deal. We introduce SDR-Arena, a framework for benchmarking two-party generative personalization at scale, and SDR-Bench, a public corpus of 50,000 customer success stories across 22 industries and 3500 enterprises. Given only pre-outcome information, an agent must reconstruct the arguments that won the deal, scored by a weighted nugget-recall metric (WCS). The best model, Claude Sonnet 4.6, reaches 55.8% WCS indicating it recovers only half the winning content-a plateau we observe across model families that costly deep-research pipelines do not close. An ablation shows the cause is retrieval, not reasoning: models improve substantially given the facts a human researcher would gather, but rarely find them through web search alone. Two studies with professional SDRs support the metric: only 48% of generated pitches were rated usable without editing, and WCS yields model rankings consistent with evaluation against expert strategies authored independently of any model output.

翻译：暂无翻译