Oeloff matriculated in 1995 from the Secondary School Grey College in Bloemfontein. He obtained the degrees B.Compt and B.Acc.Hons from the University of the Free State and completed his accounting articles at the auditing firm PriceWaterhouseCoopers in George. He joined Tuinroete Agri in 2003 and qualified as a Chartered Accountant. Oeloff is married to Andriette Kritzinger who is also a Chartered Accountant. They have two daughters Renée and Anina. He is furthermore an enthusiastic cyclist and golfer who enjoys spending time with family and friends.