Shekoski, along with Beau Burchell, Anthony Green, and Zach Kennedy, is a founding member of the post-hardcore band Saosin, having been with the group since their 2003 extended play Translating the Name. In February 2015, Quinn Allman, the lead guitarist for post-hardcore band The Used, began a year-long hiatus from performing with the group, and Shekoski was selected to fill in for him. The Used bassist Jeph Howard cited their friendship with the entirety of Saosin and Shekoski specifically as the reasons he was selected. In November 2015, The Used announced that Allman would be permanently leaving the band, and that Shekoski would be replacing him as an official member.
Shortly after that announcement, Shekoski revealed that he had been removed from Saosin "a few months [prior to November 2015]" for what he described as "questionable reasons". Shekoski expressed surprise at his removal, saying "One thing I can be sure of is that I could not and would not have done anything differently over the past years. The shows were some of the best we have ever played. It truly seemed as if everyone was happy and positivity was at an all-time high. I was proud of the new music we were creating and to be turned away right before we tracked the record that we had spent years writing and our entire career working towards is saddening at best and angering at worst. If anyone's heart or commitment to Saosin could have possibly been in question, it certainly wasn't mine, ever."
In January 2018, following a business dispute regarding payment after the release of The Canyon and subsequent promotional tour, Shekoski was dismissed from the band. In March 2018, The Used removed Justin Shekoski from their band members section on Facebook and edited him out of their promotional photos. On May 4, 2018, gossip reports surfaced of the remaining members of the Used filing a restraining order against Shekoski alleging "violence against us and himself." The story alleged that Shekoski stated that "retaliation is the only way to get justice. Those fucks ruined my life and stole my creative work." The report also alleged that Shekoski sent text messages to The Used with threats of suicide by hanging at one of their shows, to which the band responded, "Even and especially in the toughest times, the threat of suicide should never be taken lightly." Following a hearing in August 2018, the judge rejected the band's request to make the order permanent citing a lack of evidence. Shekoski's attorney issued a statement stating, "the failed move for a permanent restraining order was nothing more than a ruse" to cheat his client out of royalties for the band's album, The Canyon.

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