Raised in a military family, Raymond was commissioned into the United States Air Force in 1984 after graduating from Clemson University.

[6][7] As an Army captain, civil engineer Charles Raymond commanded a delegation that went to Northern Tasmania to time the transit of Venus in December 1874.

He remained there until 2000, at which time he assumed command of the 5th Space Surveillance Squadron located at RAF Feltwell in England.

The following year, Raymond returned to the United States and became deputy commander of the 21st Operations Group.

For two years after that, he was assigned as a transformation strategist to the Office of the United States Secretary of Defense.

In 2005, he returned to Vandenberg Air Force Base and assumed command of the 30th Operations Group.

[10] In 2009, Raymond was reassigned to Air Force Space Command as director of plans, programs, and analyses.

From July 2012 to January 2014, he served as director of plans and policy of the United States Strategic Command at Offutt Air Force Base.

[12] He relinquished command to Lieutenant General David J. Buck on August 14, 2015, to return to the Pentagon and serve as the deputy chief of staff for operations of the U.S. Air Force.

[20] On March 22, 2019, he was nominated to lead that unified combatant command, and was then confirmed by the United States Senate on June 27.

This was the first time the U.S. military has publicly identified a direct threat to a specific American satellite by an adversary.

[29] The National Defense Authorization Act for Fiscal Year 2020, which also created the Space Force, included a provision which allowed the chief of space operations to concurrently serve as commander of the combatant command for one year.

In 2017, he wrote in a Defense One article that while he applauded the increased focus on space as a warfighting domain, what is needed instead is deeper integration and more resources.

[38] Together with other members of the Joint Chiefs of Staff, Raymond denounced the 2021 United States Capitol attack.

[39] Raymond, and almost all the other Joint Chiefs of Staff members, went into quarantine in October 2020 after coming into contact with Admiral Charles Ray, who tested positive for COVID-19.

[44][45] During the ceremony, Secretary Frank Kendall III called Raymond the "father of the Space Force".

[49] In May 2023, he joined an investment firm, Cerberus Capital Management, as a senior managing director on the company’s supply chain and strategic opportunities platform, providing strategic guidance on a portfolio of investments in technology, aerospace, and defense modernization areas.