One of the key factors to construct a productive whole-cell biocatalytic cascade may include the design of the biotransformation pathways, discovery and engineering of the cascade enzymes, and functional and balanced expression of the cascade enzymes in microbial cells as well as systematic engineering of the whole-cell biocatalytic cascades. Such issues are covered in this review exemplified for the biotransformation of renewable fatty acids into industrially relevant oleochemicals (e.g., medium-chain fatty acids such as n-nonanoic acid, 9-hydroxynonanoic acid, 9-aminononanoic acid, and 1,9-nonanedioic acid) as model systems.