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Cliff Crosland's work experience begins with their current role as CEO and Co-founder at Scanner.dev, where they direct the indexing and searching of S3 data lakes. Prior to this, they worked at Cisco as a Principal Engineer, leading the engineering effort for the Webex Relationships Graph. Cliff also served as an Engineering Technical Lead during their time at Cisco. Before Cisco, Cliff was a Software Engineer at Accompany, where they built the company's core data platform and services, which were later acquired by Cisco. Cliff co-founded and served as the CTO of Seed Equity Ventures, a registered Broker Dealer with the U.S. Securities and Exchange Commission. At Addepar, they worked in Java and Scala to build the backend financial engines and native desktop UI as a Software Engineer. Cliff also co-founded and served as the CTO of RedeemPlus. Their early career includes roles as a Computer Science Section Leader at Stanford University and as a Software Developer Intern at Amazon.com.

Cliff Crosland obtained a Bachelor of Science (BS) degree in Computer Science from Stanford University, completing their education from 2006 to 2012.