[9][10] After seeing limited playing time with the Golden Hurricane, Westling transferred to Southwestern College in Chula Vista, California.
[11] In his lone season with the Jaguars in 2007, he completed 173-of-325 passes for 2,087 yards and 14 touchdowns with 12 interceptions,[7] earning second-team all-Foothill Conference honors.
[19] As a senior in 2009, Westling again substituted an injured Lindley on the road and threw his first passing touchdown, an eight-yard toss to Roberto Wallace, in a 34–20 loss at Idaho.
[21][22] In 2013, he served as quarterbacks coach at Southwestern College in Chula Vista, California, while doing his student teaching at a nearby high school.
[23] He secured his first-ever win as a head coach in a 36–27 victory against rivals Hilltop High School, claiming the Kiwanis Trophy.
[27] They also made four straight appearances in the CIF San Diego Section (CIF-SDS) Division III playoffs,[28] including a semifinal run in 2017 despite having to play all of their home games on the road due to stadium renovations.
[29] In early 2020, Westling was hired as head football coach at Eastlake High School, where he was previously a student teacher.
[31] In his first season at the helm, he led the Sundevils to a 10–2 record, a share of the Palomar League title, and an appearance in the CIF-SDS Division III semifinals.
[32][33] His father, Kurt, served as the head football coach at Aliso Niguel High School from 2010 to 2019, though he was offensive coordinator when Drew played.