Oberhelman was raised in Woodstock, Illinois, where his father was a John Deere salesman.

[8] Oberhelman attended Millikin University, where he was a member of Sigma Alpha Epsilon.

[1][2] He became a Caterpillar Vice President in 1995, serving as Chief Financial Officer from 1995 to 1998.

[2][9] He succeeded Jim Owens as CEO on July 1, 2010 and as Executive Chairman of the Board on November 1, 2010.

of $16.9 million, a sixty percent increase from his earnings the previous year.