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Jim O'Leary has a long and varied work experience. Jim began their career in 2001 as an intern at Deitel & Associates. In 2003, they were an Intern in Security Engineering and Incident Response at America Online. In 2004, they were a Software Security Engineer at Microsoft's Health Solutions Group, where they were awarded a Gold Star Award. From 2011 to 2015, they held several Security Management Positions at Twitter, where they launched 2FA for Twitter accounts, the bug-bounty program, a rewrite of production login systems, and account anomaly detection. From 2015 to 2019, they were VP of Engineering at Signal Messenger, a fully-remote, 501c3 nonprofit organization, building free open-source tools for private communication.

Jim O'Leary received their BS in Computer Science & Psychology from Rensselaer Polytechnic Institute in 2004. Afterward, they attended the University of Washington and earned their MS in Computer Science in 2011.