人 sits on top — a stylised standing figure. Combined with 止 (foot) underneath, 企 originally pictured a person rising onto their tiptoes to look ahead. The radical here also indexes the character in the person section.
止 is an old foot-print pictograph. Person + foot = standing tall on the toes, straining to see further — the literal sense of 企. From "looking far" came the modern meanings "to plan, expect, undertake" and the noun 企业 (enterprise).
