Jake Drollinger

Aspire Teacher Residency Recruitment and Admissions Specialist

Jake Drollinger hails from Sheboygan, Wisconsin … also known as the Malibu of the Midwest. After graduating from high school, he decided to take a gap year and joined City Year in San Jose as an AmeriCorps member. He spent that year in service leading high school students learning curriculum and community-based projects. Feeling such a deep connection to the impact, he spent the following nine-plus years working to share service as a pathway for young adults. Jake took on a variety of roles in the Recruitment and Admissions department at branches in San Jose, Milwaukee (Start-Up), Los Angeles, and remotely as a regional team. Some of Jake’s proudest accomplishment from his time at City Year include establishing CY Milwaukee’s first alumni board, developing a nationally implemented database management system, leading the effort in paperless admissions, and elevating operations strategy department-wide. Jake is a minority owner of the Green Bay Packers and loves all Wisconsin sports teams as well as the San Jose Sharks. He enjoys spending time with friends and family, taking in an eclectic range of musical performances, surfing, and the more-than-occasional burger from In-N-Out.