He served as President of the B&O Railroad from 1910 until 1941. He guided the company through labor struggles, World War I, and the Great Depression. He began his railroad career as a laborer, earning a dollar a day. He was soon promoted to fireman, and was elevated to locomotive engineer before he reached the age of twenty. By the time he ascended to the B&O presidency, he was thoroughly experienced in every aspect of the railroad industry.
Willard was at the helm when the operating unions threatened a nationwide strike shortly before America entered World War I. He was instrumental in averting the strike and led the railroad through the turmoil associated with the war effort. There was a huge expansion in B&O operations during his tenure, and he was responsible for vast improvements in the efficiency of the company he ran for over three decades.