Evaluation protocols can lag behind LLM capabilities. Programmatically verified benchmarks cover narrow surface constraints, whereas real-world instruction following and agentic workflows require judging semantic, contextual, and policy-dependent behavior. We study expert-curated rubric-based evaluation as a unified mechanism for measurement and reinforcement-learning rewards across two settings: complex instruction following and enterprise agentic tasks. We identify rubric-design choices that affect reward quality, including maximum viable atomicity, intent-aware criterion design, and LLM-judge calibration. We introduce ComplexConstraints, an expert-curated instruction-following suite comprising a public 75-prompt benchmark with 1,559 rubric criteria and a disjoint 1,000-prompt training set, with 10-40 atomic criteria per prompt. Empirically, rubric rewards improve training in both fixed task datasets, such as ComplexConstraints, and stateful RL environments, such as CoreCraft. Training a 4B model on ComplexConstraints improves mean criterion pass rate by +15.5 pp on a held-out split, bringing it within 0.5 pp of the untrained baseline of a roughly 60x larger Qwen3 model, and the gains transfer to external benchmarks the model never saw during training: +8.4 pp on AdvancedIF and +10.1 pp on MultiChallenge. In CoreCraft, rubric-reward RL likewise transfers to out-of-distribution benchmarks (+4.5 pp BFCL, +7.4 pp tau^2-Bench, +6.8 pp Toolathlon). These results show that expert-authored rubrics provide effective evaluation targets and scalable reward signals for improving LLM instruction following and agentic behavior.

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