Youth and college Heinemann attended
Christian Brothers College High School, and played
college soccer at
Rockhurst University from 2006 to 2008, where he was named to the NSCAA/adidas NCAA Division II Men's All-America Team as a sophomore and as a junior. During his time at Rockhurst, Heinemann accumulated 36 goals and 21 assists while appearing in 60 games. He also played in the
USL Premier Development League for
St. Louis Lions, where he was a prolific goalscorer, netting 35 times in 36 games over three seasons with the team.
Professional Heinemann was signed to his first professional contract by the
Charleston Battery after impressing head coach
Michael Anhaeuser during a pre-season trial. He made his professional debut on April 11, 2009, in Charleston's USL1 season opener against the
Vancouver Whitecaps and scored his first professional goal on June 7, 2009, in a 1–1 tie with the
Austin Aztex. Heinemann continued with Charleston in 2010, helping them to the 2010 USL Second Division title. Following the conclusion of the 2010 USL2 season, Heinemann signed with the
Carolina RailHawks for the remainder of the
USSF Division 2 Professional League regular season and playoffs. Heinemann scored the game-winning goal in the RailHawks semifinal victory over the
Montreal Impact. During that season, the Railhawks made a run to the title match, but lost to the Puerto Rico Islanders. He was named MVP of the championship game. On January 6, 2011, Heinemann signed with
Columbus Crew of
Major League Soccer. He played his first game with the Crew on March 19, 2011, in their 2011 MLS season opener against
D.C. United. Heinemann was released by Columbus following the 2012 season and signed with
Vancouver Whitecaps FC on January 23, 2013 scoring his first MLS goal for the team on September 1, 2013, in second-half stoppage time, to help his team draw 2–2 with
Chivas USA. The club declined his option along with seven other players at the end of the 2013 season. He was signed by
NASL expansion side
Ottawa Fury on February 2, 2014, ahead of their inaugural campaign. Ottawa advanced to the
2015 Soccer Bowl, but despite 2 goals from Heinamann they were defeated by the New York Cosmos. Heinemann signed with
Tampa Bay Rowdies on December 14, 2015. Heinemann signed with new NASL club
San Francisco Deltas on February 6, 2017. The club won the post-season playoffs for the league but folded shortly after due to financial difficulties.The finals match saw Heinemann score the winning goal on a penalty kick in the 19th minute as the Delta's claimed the
2017 Soccer Bowl. Heinemann signed with USL club
FC Cincinnati on December 5, 2017. However, he was released by the club before the 2018 season started due to a failed entry physical. On March 29, 2018, Heinemann signed with
Penn FC of the
United Soccer League.
Coaching Heinemann retired from professional soccer following the 2018 season. On April 16, 2019, he was named an assistant coach with the
Belmont Bruins men's soccer team. In February 2022, Heinemann was named head coach for the
United States boys' national under-15 soccer team. Under Heinemann's stewardship the team won 6 consecutive matches, while outscoring their opponents 26–5, to claim the 2023 CONCACAF Boys' Under-15 Championship Final. In January 2025, Heinemann joined the staff of
Major League Soccer side
Chicago Fire as an assistant coach. ==Coaching statistics==