Could a North Dakota farm boy with a smallish frame, bookish appearance, understated speaking voice and aw-shucks humility possibly be a good fit to lead a powerhouse, cosmopolitan private school for American students living abroad, whose governing board consists mainly of high-flying corporate executives and well-heeled attorneys? The answer today is a decided yes, but the 12-member governing board of the resource-rich Singapore American School harbored serious doubts when Bob Gross submitted his candidacy for the top post five years ago. The school board's search consultant assessed his chances so dimly against an experienced pool of international headmasters that Gross, then in his 18th year as superintendent in Brainerd, Minnesota, had to pay his own way to Oregon for a preliminary interview. This article contains a brief profile of Bob Gross and the work he has done as a superintendent.