Ross got his first job at the Royal Dornoch Golf Club, where he played while growing up, working as a greens keeper.

[2] With the help of an American agronomy student, fellow Scotsman Robert White from St. Andrews, Ross decided to move to America.

[5][2] Later in 1899, with the encouragement and support of Harvard astronomy professor Robert W. Willson, he obtained his first job in America at Oakley Country Club in Watertown, Massachusetts.

While working at the Oakley Country Club, Ross had left an impression on the president of the Boston Athletic Association at the time, Edward E. Babb.

Babb introduced Wyckoff to Ross later that year, bringing him back to the course, where he suggested key changes, but was unable to prepare plans as he had just signed a two-year contract as professional for the Essex County Country Club.

[7] He would work with the Mount Tom Club for many years, welcoming Holyoke neighbors visiting his winter home in Pinehurst,[12] completing a full redesign of the Mt.

[14] Ross's work in Holyoke would remain largely untouched until the construction of I-91 in 1965 left only 5 fairways of his design today.

[16] Some of his early work was in Virginia and includes Jefferson Lakeside Country Club and Sewell's Point Golf Course.

Ross often created holes which invited run-up shots but had severe trouble at the back of the green, typically in the form of fall-away slopes.

[1] All of these exemplify his naturalness design philosophy which did not require intense earth moving, he simply let the lay of the land dictate what each and every hole should be.