Findings are presented from a year-long study of a cross-sector collaboration to prepare underrepresented students for postsecondary education and beyond. The LEAD (Leadership Education and Development) Program in Business is an initiative involving universities, corporations, a federal government agency, and a nonprofit coordinating body in an effort to introduce students to business education and careers in business. This paper analyzes and compares (1) the starting conditions catalyzing the involvement of different sectors, (2) sustainability factors, (3) negotiation of the terms of involvement, (4) the actual experience of partnership, and (5) the difference made by a coordinated approach to pipeline development.