Alphabettes is a global network of women type professionals that came together with the aim to support and promote the work of other women in the fields of type, typography, and the lettering arts. In spring 2016, a group of Alphabettes members created The Alphabettes Mentorship Program. It started as an effort to reach out and help entry-level professionals of all genders to immerse themselves in the type community. More than four years since its first launch, the mentorship program has more than 200 participants from all across the world. It is coordinated by a small international team of volunteer-matchmakers. The team reviews and discusses each application individually, makes the connection between each Mentor and Mentee, follows their progress, and finds ways to implement feedback in order to keep this program running smoothly and relevant. In this talk the matchmakers team will share the story of the Alphabettes Mentorship Program. This will be a sneak-peek behind the scenes, where we will share our matchmaking process, our challenges, as well as some of our inspirational Mentees and Mentors success stories. Through this talk we hope to show how a volunteer-based outreach program can be built and managed, how it is possible to create impactful global connections within our community and how we all benefit from its rewarding activity.