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 vice-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.[4]
In 1950, he was admitted as an honorary member of the New York Society of the Cincinnati.[5]
Wood, once again, served as an honorary chairman for Sears from 1968 until shortly before his death in 1969, leaving a good portion of his stocks to family members.