Prior to his new appointment, Dillon was Executive Vice President, General Counsel and Corporate Secretary of Sun Microsystems. Sun Microsystems, founded in 1982 and headquartered in Santa Clara, California, sold computers, computer components, computer software, and information technology services until it was acquired by Oracle Corporation in early 2010. Until the sale of the company, Dillon was responsible for corporate compliance. Legal, export and related functions. While at Sun, Dillon also ran ''The Legal Thing,'' a personal blog that showcased his ideas about the future of the legal profession.
Before his time at Sun Microsystems, Dillon was General Counsel of ONI Systems. Dillon was responsible for
legal affairs and security and risk management. ONI Systems developed and marketed optical telecommunications systems designed to address bandwidth and service limitations of regional and metropolitan networks. CIENA Corporation, supplier of telecommunications networking equipment, software and services, acquired ONI Systems and Dillon oversaw that acquirement.
Dillon acquired his Bachelor of Arts Communications and Sociology from the University of California, San Diego. He went on to earn his J.D. from Santa Clara University School of Law. Silver Spring Networks, headquartered in Redwood City, California, now has Dillon to oversee all of its legal operations.