Small language models are attractive for production deployment due to their low cost, fast inference, and ease of specialization. However, adapting them to a specific task remains a challenging engineering loop, driven not by training itself but by surrounding decisions: data curation, failure diagnosis, regression avoidance, and iteration control. We present Pioneer Agent, a closed-loop system that automates this lifecycle. In cold-start mode, given only a natural-language task description, the agent acquires data, constructs evaluation sets, and iteratively trains models by jointly optimizing data, hyperparameters, and learning strategy. In production mode, given a deployed model with labeled failures, it diagnoses error patterns, constructs targeted training data, and retrains under explicit regression constraints. To evaluate this setting, we introduce AdaptFT-Bench, a benchmark of synthetic inference logs with progressively increasing noise, designed to test the full adaptation loop: diagnosis, curriculum synthesis, retraining, and verification. Across eight cold-start benchmarks spanning reasoning, math, code generation, summarization, and classification, Pioneer Agent improves over base models by 1.6-83.8 points. On AdaptFT-Bench, it improves or preserves performance in all seven scenarios, while naive retraining degrades by up to 43 points. On two production-style deployments built from public benchmark tasks, it raises intent classification from 84.9% to 99.3% and Entity F1 from 0.345 to 0.810. Beyond performance gains, the agent often discovers effective training strategies, including chain-of-thought supervision, task-specific optimization, and quality-focused data curation, purely from downstream feedback.