Abstract: AI agents increasingly use files and software tools to produce professional deliverables. Such work draws on materials, decisions, and feedback accumulated across assignments. We introduce OfficeTown, a generative simulation framework for professional organizations in which tasks and their context arise from continuing organizational work. From a natural-language description of an organization's purpose and activities, OfficeTown initializes an organization whose members coordinate work, delegate bounded assignments to assistant agents, and review their deliverables. Artifacts, decisions, and unresolved matters persist and shape subsequent work, while responsibilities and permissions determine what each member can see and do. We curate work requests, their context, and review feedback into executable resources for evaluation and learning. We construct OfficeTown Bench with 406 tasks and 4,836 evaluation criteria from 23 simulated organizations across eight professional domains, incorporating domain-expert feedback. Frontier-model evaluations reveal substantial remaining headroom. Supervised fine-tuning and on-policy distillation on OfficeTown data substantially improve Qwen3.5-9B on external professional-work benchmarks, including GDPval. Supplementary evaluations show that the principal--assistant harness achieves higher scores than the single- and multi-agent baselines tested. These results highlight the value of organizational simulation in generating work-grounded data and environments for the continued development of generalist agents.