Born in Stone Mountain, Georgia,[citation needed] Wolff played three years of college soccer at the University of South Carolina, where he scored 21 goals and eight assists in 43 games.

In addition, Wolff played and captained varsity soccer at Parkview High School, Lilburn, Georgia.

However, British immigration officials denied Wolff a work permit based on the fact he had failed to play the required 75% of the U.S. national team's games in the previous two years.

[6] On December 15, 2010, Wolff was selected by D.C. United in Stage 2 of the 2010 MLS Re-Entry Draft and immediately signed a one-year contract with a club option for 2012.

On July 23, 2019, Wolff was announced to be the first head coach of MLS expansion team Austin FC, who began playing with the 2021 season.

[11] Austin FC had 9 wins, 21 defeats, and 4 draws in their expansion season under Wolff, finishing in 12th in the Western Conference, one point above Houston in last.

The team went into their match on October 30 against Dallas with a chance to win the first MLS Copa Tejas, but a 2–1 defeat meant that they finished in third.

[21] Under Wolff's guidance the team continued to be successful, exciting fans by making their way to the Western Conference Finals,[22] losing 3–0 to LAFC in a lackluster performance to end their season.

[23] On October 6, 2024, Austin FC parted ways with Wolff after falling short of qualifying for 2024 MLS Cup playoffs.