A resident of Ann Arbor, MI, Benedict has had a diverse set of jobs. After graduating from University of Chicago with a B.S. in Computer Science, he started working on networking and streaming in the Digital Cinema group at Dolby Laboratories. During a year in Cambridge, UK, he was the second full-time employee at successful startup Ellexus making developer tools. In Ann Arbor, he worked on OCR and medical imaging with NovoDynamics, before moving to Automattic to work in the WordPress space.