Woodruff was a successful businessman and was involved in several banks and corporations. He was a director of the Mechanics Bank of New Haven, the Connecticut Savings Bank, and the Connecticut Computing Machine Company. He was vice president of the Federal Adding Machine Company. In addition, Woodruff was president of Grace Hospital of New Haven and C. S. Mersick Company, a manufacturer and wholesaler of heavy hardware, railroad supplies, machinist supplies and other metal products. Beginning in 1896 became active in the
state militia, and in 1899 he was appointed
aide-de-camp to Governor
George E. Lounsbury with the rank of
colonel. In 1902 he became a member of the Connecticut Society of the
Sons of the American Revolution. A
Republican, he was elected to one term in the
Connecticut State Senate in 1903, and was chosen the Senate's
President pro tempore. He was President of
New Haven's Chamber of Commerce from 1905 to 1907. Woodruff became the
71st Lieutenant Governor of Connecticut in 1905. He held that position until 1907. Winning the 1906 Republican gubernatorial nomination, Woodruff became the
Governor of Connecticut on January 9, 1907. During his term, he vetoed several acts of the legislature, arguing that they were too costly. Woodruff remained active in his business. He became a member of the Union League Club. He also served as a member of the New Haven Young Men's
Republican Club. ==Death==