OSS familiarity is increasingly an important skill for those starting their career in software, but students often graduate from schools without this key practical experience. In 2018 Datadog launched an open source apprenticeship program to help bridge this gap. Students joining the program are mentored throughout a 4 month program, as they contribute to upstream projects. In this session Jeremy and Ilan will share our experiences building the program, explain the benefits it brings to an organization, and provide tips that will help others implement similar programs in their own organizations.