Before taking the reins in 2023, Caines served as the deputy chief innovation officer and as a senior adviser on technology when he first joined the city in May 2021.
Caines, who holds a law degree from the University of Miami School of Law, has been focused on the intersection of law and technology for quite a while. Before joining the ranks of San Jose public service, he served as a non-residential fellow with the Stanford Center for Legal Informatics, CodeX, as a technology clerk with Legal Services of Greater Miami, and as a research fellow with the Cyber Civil Rights Initiative.
“I’m especially grateful for Stephen’s guidance and mentorship in navigating our annual budget process. His thoughtful leadership and strategic perspective will be deeply missed,” Budget and Innovation Advisor Keith Hertzberg wrote in a LinkedIn post.
The departing public official noted in his announcement that he is preparing for his next role, but did not give additional detail.
“This role has given me the opportunity to work on a broad portfolio spanning digital inclusion, digital privacy, library services, information technology, economic development, employee upskilling, public-private partnerships and AI integration into city services and community programming,” Caines continued in the post.
The city is currently advertising the position and will begin reviewing applications June 8, though the position will remain open until filled.
In addition to his Juris Doctor from the University of Miami, Caines holds a bachelor’s in legal studies from the University of Central Florida.
