He has managed at the full-season Class A level with the Beloit Snappers, Quad Cities River Bandits, Fort Myers Miracle, Greenville Drive and Salem Red Sox.
In 2013, Boles spent his third consecutive season as skipper of the Portland Sea Dogs, the Red Sox' Eastern League affiliate.
[3] Each of his Portland teams finished below .500, compiling a composite record of 195–229 (.460), but Boles' Seadogs developed players such as Xander Bogaerts, Jackie Bradley Jr., Drake Britton, Will Middlebrooks, Junichi Tazawa, Alex Wilson and Brandon Workman, who all contributed materially to the MLB Red Sox' 2013 American League pennant and World Series triumph.
In 2014, Boles led Pawtucket to a 79–65 record, a wild-card playoff berth, and the fourth Governors' Cup championship in club history.
The 2014 Pawtucket Red Sox also developed Major League prospects Matt Barnes, Mookie Betts, Garin Cecchini, Rubby De La Rosa, Henry Owens, Anthony Ranaudo, Travis Shaw, Blake Swihart, Christian Vázquez, Allen Webster and others.