After the leaving the army again in 1919, Wood became an executive at Montgomery Ward, eventually becoming a vice-president of the company. In 1924, he left Montgomery Ward to take a position of vice-president of Sears Roebuck. He became one of the most important leaders in that company's history, serving as president from 1928 until 1939 and as chairman from 1939 until 1954. Under his leadership, Sears shifted the focus of its operations from mail-order sales to retail sales at large urban department stores. Wood also created Allstate Insurance as a subsidiary of Sears.