His directorial debut My Boss, My Hero is about a gangster who is sent back to school, while Sex Is Zero has been compared with American Pie.

[5] Yoon made his debut in the film industry by winning the grand prize of the scenario contest (moon trip) hosted by Taechang Heungup.

In 2016, CJ ENM acquired a 51 percent stake in JK Film, making it a subsidiary of the company.

[7] On October 25, 2022, CJ ENM announced its plan to integrate other production affiliates, centered on its affiliate CJ ENM Studios, to create synergy by combining their content production capabilities.

Yoon sold his 2,388 shares of JK Film, to CJ ENM for a total of 5.1 billion won.