We propose OutboundEval, a comprehensive benchmark for evaluating large language models (LLMs) in expert-level intelligent outbound calling scenarios. Unlike existing methods that suffer from three key limitations - insufficient dataset diversity and category coverage, unrealistic user simulation, and inaccurate evaluation metrics - OutboundEval addresses these issues through a structured framework. First, we design a benchmark spanning six major business domains and 30 representative sub-scenarios, each with scenario-specific process decomposition, weighted scoring, and domain-adaptive metrics. Second, we develop a large-model-driven User Simulator that generates diverse, persona-rich virtual users with realistic behaviors, emotional variability, and communication styles, providing a controlled yet authentic testing environment. Third, we introduce a dynamic evaluation method that adapts to task variations, integrating automated and human-in-the-loop assessment to measure task execution accuracy, professional knowledge application, adaptability, and user experience quality. Experiments on 12 state-of-the-art LLMs reveal distinct trade-offs between expert-level task completion and interaction fluency, offering practical insights for building reliable, human-like outbound AI systems. OutboundEval establishes a practical, extensible, and domain-oriented standard for benchmarking LLMs in professional applications.