Jessica McKellar is a founder and the CTO of Pilot, a bookkeeping firm powered by software. Previously, she was a founder and the VP of Engineering for Zulip, a real-time collaboration startup acquired by Dropbox, where she then served as a Director of Engineering. Before that, she was a computer nerd at MIT who joined her friends at Ksplice, a company building a service for rebootless kernel updates on Linux that was acquired by Oracle. She is also a long-time leader in the open source Python programming language community and has served as a Director for the Python Software Foundation, the non-profit stewarding organization for the language. Since 2012 she has led the community outreach initiatives for PyCon, an annual Python conference lauded for elevating the standards for effective diversity and inclusion in open source communities. For her Python community work she was awarded the O'Reilly Open Source Award. Open source meets criminal justice reform in Jessica’s work with The Last Mile, a job training and re-entry program that has implemented the first computer programming curriculum inside a US prison, at San Quentin.