Winford was formerly the program director of KATS-FM and KIT-AM in Yakima, Washington, the operations manager of KCTR, KMHK, KKBR and KBUL-AM in Billings, Montana, the program director of CHBN/Edmonton, Canada, program director of KKBZ-FM and KHIT-FM in Fresno, California, and the operations manager of KURQ, KSLY & KSTT in San Luis Obispo, California.
Winford held various roles, including program director at KATS-FM and KIT-AM in Yakima, Washington, operations manager at KCTR, KMHK, KKBR, and KBUL-AM in Billings, Montana, program director at CHBN/Edmonton, Canada, and program director at KKBZ-FM and KHIT-FM in Fresno, California, as well as operations manager at KURQ, KSLY & KSTT in San Luis Obispo, California.