Early in his academic career, Ollie James Wilson taught and administered at public schools in Kentucky from 1928 to 1940. During World War II he served as an infantry officer and then later as assistant chief-of-staff for intelligence until he was evacuated from Guam after sustaining a serious injury. He received numerous decorations when he retired as a colonel in December 1945. Returning to his academic career, he taught English, speech and the humanities at the University of Tennessee, University of Georgia and Morris Harvey College in Charleston, West Virginia. Wilson earned his doctorate from the University of Kentucky in 1951 and was serving as chairman of the division of humanities at Morris Harvey College in West Virginia when he was tapped for the job at Findlay College. He was originally hired as executive vice president of Findlay College to assist President Fox in his duties. Soon after he arrived, Fox was hospitalized. Due to Fox's continuing illness, Wilson was named president of Findlay College on Feb. 1, 1959 and was inaugurated on June 6, 1959.
Marked by a time of extraordinary change and transformation, Wilson's primary task as president was to prepare the College for accreditation by the North Central Association (NCA). The number of faculty with doctoral degrees increased, the curriculum was evaluated and working conditions improved. Based on the accrediting body's objections, Wilson convinced the board and the church to limit the authority of the church over the board of trustees. A development campaign was started and buildings were added to the campus including the completion of Lovett Hall, the Alumni Memorial Union, Brewer Science Hall and the expansion of the library. The administration was reorganized including the establishment of the Office of Student Affairs. Financial operations were further stabilized and when Findlay's self-survey was submitted in June of 1961, the College was added to the list of accredited institutions.
After the College was accredited, Wilson continued to develop the structure of the institution including the offices of the Registrar and Admissions. He centralized the primary functions of the College including Business Affairs, Student Affairs, instruction and development under the direction of four vice presidents who reported directly to him. He also reorganized the academic program into five schools: the Evening School, the School of Humanities and Sciences, the School of Fine Arts, the School of Education and the School of Business Administration. Wilson also made several developments to strengthen the College reputation. He requested the formation of a women's auxiliary, later to be called Town and Campus, which worked to improve the College's public image and made the college attractive to women students. He awarded the first distinguished alumnus awards in 1962 and brought internationally and nationally recognized speakers to campus.
While enjoying enormous success in a short period of time, Wilson's program of substantial changes eventually reaped charges of an autocratic style, with dissension and high turnover among the faculty and protests among the students. The NCA visited with a special re-examining committee in May 1963, and reported disappointment at the severe morale problems that had developed so quickly since the last visit. Coupled with ill health from a back injury during the war, President Wilson resigned in August 1963. After leaving Findlay he became professor of philosophy at Western Kentucky University. He also served two years as an accreditation consultant in the Chicago area and then returned to Western Kentucky to become director of institutional research and professor of English and speech. Wilson retired in 1975 after open-heart surgery for replacement of an aortic valve and became a professor emeritus at Western Kentucky University.