The Toronto Blue Jays selected Schimpf in the fifth round of the 2009 Major League Baseball draft. He signed with the Blue Jays and was assigned to the Gulf Coast Blue Jays of the Rookie-levelGulf Coast League, where he played in two games, before being promoted to the Auburn Doubledays of the Class A-Short SeasonNew York-Penn League. In 36 total games in 2009, Schimpf batted.293 with three home runs and 14 runs batted in. In 2010, Schimpf played for the Lansing Lugnuts of the Class AMidwest League and the Dunedin Blue Jays of the Class A-AdvancedFlorida State League, hitting.237 with eight home runs and 52 RBIs in a combined 110 games. He was named a mid-season All-Star for Lansing. Schimpf began the 2011 season on the disabled list, not appearing in a minor league game until June 9. In 57 games played for Dunedin that year, he hit.240 with 10 home runs and 36 RBI. Schimpf began 2012 with Dunedin, and was named a mid-season All-Star for the second time in his career. In late July, he earned a promotion to the New Hampshire Fisher Cats of the Class AAEastern League, where he finished the 2012 campaign. In a career-high 129 games played, Schimpf batted.269 with 22 home runs and 76 RBIs. Schimpf played the entire 2013 season with New Hampshire, where he hit.210, 23 home runs, and 65 RBIs in 126 games. He split the 2014 season with New Hampshire and the Buffalo Bisons of the Class AAAInternational League, appearing in 117 games and hitting.227 with 24 home runs and 58 RBIs. In the offseason, Schimpf appeared in 26 games for the Venados de Mazatlán of the Mexican Pacific League. Schimpf split the 2015 season between New Hampshire and Buffalo, and in 107 games hit.250 with 23 home runs and 63 RBIs.
San Diego Padres
Schimpf became a free agent after the 2015 season, and signed with the San Diego Padres. Schimpf began the 2016 season with the El Paso Chihuahuas of the Class AAA Pacific Coast League. In 98 games at the level with Buffalo over two seasons, Schimpf hit.193 with 12 home runs and 28 RBIs. However, Schimpf hit.355/.432/.729 with 15 home runs and 48 RBIs in 51 games before his call-up, his slugging percentage and 1.160 on-base plus slugging leading the league at the time. He had earned Player of the Week honors in the PCL on June 5. The Padres promoted Schimpf to the major leagues on June 14, 2016, making his debut that night against the Miami Marlins as a third baseman. Schimpf hit his first career home run onJuly 1 against the New York Yankees. On July 24, Schimpf set a Padres rookie record by slugging his ninth home run of the calendar month. He hit his record-breaking home run against Nationals reliever Shawn Kelley to tie the game in the eighth inning, leading to a 10-6 Padres victory. Through July 27, his 9 home runs also lead the entire league for the month of July. Schimpf won the National League Rookie of the Month Award for July. On August 12, 2016, Schimpf hit his first career grand slam off of New York Mets starting pitcher Logan Verrett. Schimpf made the Padres' Opening Day roster in 2017 as their starting third baseman.
Los Angeles Angels
After the 2017 season, the Padres traded Schimpf to the Tampa Bay Rays for Deion Tansel. On March 3, 2018, the Rays designated Schimpf for assignment. Two days later, Tampa Bay traded Schimpf to the Atlanta Braves in exchange for cash considerations. On March 31, Schimpf was traded to the Los Angeles Angels in exchange for catcher Carlos Pérez. On April 7, 2018, the Angels called up Schimpf and he pinch-hit later that day. He was released by the Angels on May 22.
Mexican Pacific League
In 2014, Schimpf appeared in 26 games for the Venados de Mazatlán of the Mexican Pacific League. On October 18, 2018, Schimpf signed with the Naranjeros de Hermosillo of the Mexican Pacific League. He was released on October 24, 2018 after failing to travel with team for a series in Culiacán.