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Motivated by the need to rapidly and equitably upskill workers in response to technological advances and social change, a team funded by the US National Science Foundation Convergence Accelerator program has developed and piloted an application called SkillSync that (i) helps employers identify and communicate the skills their workers require; (ii) connects employers to non-degree college programs that can provide relevant training; (iii) helps those programs align their offerings with employer requirements; and (iv) facilitates the exchange of proposals to offer training. This paper describes SkillSync and explains how Artificial Intelligence (AI) is used to automate skills extraction and align training resources with training requests. This paper then discusses the steps taken to ameliorate possible biases and an intelligent agent that is included in SkillSync to increase transparency and trust in the application. The methods discussed in this paper are applicable to many classes of applications that use AI in training, education, and talent management