During the next decade, Sherrill briefly served as a military aide to President Theodore Roosevelt and was stationed in the Philippines and several U.S. cities.

[3] His mother was Sarah Ramseur Bost and his father, Miles Osborne Sherrill, was a Civil War veteran who had lost a leg at the Battle of Spotsylvania Court House.

He left Trinity in 1897 to attend the United States Military Academy (West Point), where he graduated at the rank of second lieutenant in 1901 with a degree in civil engineering, second in his class.

[5] In 1904, Sherrill attended the School of the Line (now the United States Army Command and General Staff College) at Fort Leavenworth, where he took infantry and cavalry courses for officers until graduating in 1906 with honors.

[1][5] After his promotion to captain, Sherrill taught at the School of the Line for three years and wrote a military text book on topography.

[5] When the United States entered World War I, Sherrill was stationed in France, where he led the 302d Engineers and served as chief of staff of the 29th and 77th Infantry Divisions.

[1][9] While also serving as military aide, Sherrill was appointed director of the Office of Public Buildings and Grounds, beginning in March 1921.

According to historian and author Eric S. Yellin, Sherrill was an "avid segregationist" and was responsible for segregating the dedication ceremony of the Lincoln Memorial.

[1][10][12] Sherrill also implemented segregation policies in the city's parks, pools, and picnic areas, by requiring installation of signs that said "white" and "colored".

"[12] One local black resident, Hattie Sewell, had won a contract to operate the Pierce Mill Tea House in Rock Creek Park.

[10] Sherrill's tenure as head of local parks and public buildings ended in December 1925 when he retired from the Army and was succeeded by Ulysses S. Grant III.

[1][14] After Grant III declined to take over the role when Sherrill left, Clarence Addison Dykstra was named the new city manager.

[16][17] Sherrill served as the organization's president, and according to academic author Michael J. Hicks, was instrumental in thwarting attempts to stop the "anti-chain store movement" by utilizing advertisements and placards.

[15] Sherrill left the American Retail Federation to return as city manager of Cincinnati, working in this role from 1937 until his retirement in 1944.