Wood joined the retail business as a general manager at Montgomery Ward and Company, where he advocated the building of retail stores to capitalize on the growing importance of the automobile. After unsuccessfully battling over the concept with Ward’s president, Wood joined Sears in 1924 to implement his vision. Building the stores in urban areas so as not to further detract from the catalog-driven rural business, Wood’s chain stores were immensely successful. In addition to this success, Wood created the Allstate Insurance Company as a subsidiary.