Master Sergeant Wilebski graduated from Mosinee High School in January 2002. On 10 February 2002, he reported to Marine Corps Recruit Depot, San Diego, California, graduating on 10 May 2002. In May 2002, Private First Class Wilebski reported to the Infantry Training Battalion (ITB), School Of Infantry-West (SOI-W), Camp Pendleton, California, graduating in August 2002. 

In August 2002, Private First Class Wilebski reported to 3rd Battalion, 4th Marine Regiment, 1st Marine Division, for service as a Rifleman. After promotion to Lance Corporal in October 2002, Lance Corporal Wilebski deployed to Kuwait in support of Operation Iraqi Freedom from January 2003 to May 2003. From January 2004 to July 2004, Lance Corporal Wilebski deployed to Kuwait in support of Operation Iraqi Freedom 2. He was assigned as a fire team leader in 3rd platoon Kilo co 3rd Battalion, 4th Marine Regiment. In May of 2004, Lance Corporal Wilebski Company was sent into Al Fallujah, Iraqi, in support of Operation Vigilant Resolve. In June of 2004, Lance Corporal Wilebski was promoted to Corporal. From January 2005 to August 2005, Corporal Wilebski once again deployed as a Squad Leader in support of Operation Iraqi Freedom. In November 2005, Corporal Wilebski was promoted to Sergeant.

Sergeant Wilebski reported to Tactical Training Exercise Control Group (TTECG), Marine Corps Air Ground Combat Center (MCAGCC) in November of 2005 for service as a Coyote. While a Coyote, Sergeant Wilebski observed all of the Infantry Battalions including all Reconnaissance Battalions, Combat Logistics Regiments/ Battalions, and Combat Engineer Battalions.

In August 2008, Sergeant Wilebski was assigned to 7th Marine Regiment Operations Shop. Sergeant Wilebski was given the billet of Operations Non-Commissioned Officer. In January 2010, Sergeant Wilebski was promoted to Staff Sergeant and deployed to the Helmand Province, Afghanistan, in support of Operation Enduring Freedom, as the Regimental Watch Chief. He returned in October 2010.

Staff Sergeant Wilebski reported to the Marine Combat Instructor School, School of Infantry-East in January 2011. He was subsequently assigned to ITB, Bravo Company. While serving with Bravo Company, he served as Platoon Commander. In November 2012, Staff Sergeant Wilebski was selected to join the Tactics Instructor Group as the Tactics Chief within Headquarters and Instructor Company. 

In May of 2014, Staff Sergeant Wilebski reported to 3rd Battalion 7th Marines, where he served as 3rd Platoon, Platoon Commander, and Platoon Sergeant. In February 2015, Staff Sergeant Wilebski left active duty as part of the Marine Corps Force Shaping Program (VSP).

Staff Sergeant Wilebski was promoted to the rank of Gunnery Sergeant in July of 2016 within the Inactive Reserves.