Miles was a ranger in the United States Army and worked in the U.S. State Department.[2] In his educational career he served as a superintendent for Harrison School District 2 in Colorado Springs.[3] Miles operated an educational consulting firm called Focal Point while in that position. The business wound down after he became Dallas ISD superintendent as his contract for DISD restricted his outside activities.[4] In Colorado Springs he tied teacher and principal pay to gains in student achievement.[3]
Dallas Independent School District
Miles created the reform effort Destination 2020 which asked for improvements to be made by 2013 and 2015.[5] Another plan, Accelerating Campus Excellence" (ACE) involved moving new principals and teachers into campuses and attracting high-performing teachers to needy campuses.[6]
Dallas County Commissioner John Wiley Price criticized Miles and called for his ouster.[5]
In 2013 the school board voted on whether to remove Miles from his position. Five members voted against and three voted for.[7] Miles' family initially moved from Colorado Springs to Dallas, but they returned to Colorado Springs in 2013 as a result of media attention on Miles' career.[8]
In 2014 Miles expressed a desire to get additional compensation in his contract.[9] Miles attempted to get amendments to his Dallas ISD contract but the board did not approve them. Miles resigned from Dallas ISD in 2015.[10]
Post-Dallas ISD
After he resigned from Dallas ISD, he founded a new chain of charter schools in Colorado, Texas, and Louisiana called Third Future Schools. Third Future schools consist of 11 public charter schools.[11]
Houston Independent School District
On June 1, 2023, Miles was appointed superintendent of Houston ISD, replacing Millard House II as part of the Houston Independent School District takeover by the Texas Education Agency.[12][6] Miles started new Texas schools which were alleged to be losing money. Third Future Schools’ 2023 audit shows of the $25 million public tax dollars being spent on Miles’ three Texas schools, $15 million was spent on teachers and supplies. The other $10 million, about 40% of the budget, was spent on unspecified administrative costs and services.[8]
Miles had a controversial first term as superintendent. Issues protested included a lack of autonomy with teacher observations, pushing to convert libraries into discipline areas,[13] HISD employee terminations, and accusations of misuse of funds. Miles allegedly misused funds by funneling money to his aforementioned charter schools.[14] Protests occurred at Houston City Hall and multiple HISD schools. [15][16] HISD has seen significant staff turnover since Miles' appointment, with more than 10,000 employees leaving as of June 2024.[17][18]
