Matthew Ebeweber
CTO and Co-Founder of Caspian, experienced in AI, fintech, and supply chain
ebeweber
San Francisco, California
Alpine, Wyoming
Joined November 2025
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Summary
Matthew Ebeweber is an experienced software engineer and entrepreneur, currently serving as CTO and Co-Founder of Caspian. At Caspian, he is building an AI-native platform focused on optimizing duty drawback processes, leveraging technology to help companies navigate complex tariffs and maximize refunds in global trade. linkedin+4
His expertise extends to fintech and supply chain, demonstrated by his previous role at Flexport where he helped build its lending arm into a billion-dollar business and developed internal customs products. This background provides a strong foundation for Caspian's mission to demystify customs duties. linkedin+1
Matthew has a proven track record in applying artificial intelligence and automation to real-world problems. At Clara Labs, he contributed to and wrote about their human-in-the-loop AI system for intelligent scheduling, detailing how the system suggests and confirms meeting times efficiently. medium+1
He is also a contributor to the open-source community, evidenced by his 'flake8-mutable' project, a static analysis tool for Python to catch common programming pitfalls related to mutable default arguments. github+1
As a student, Matthew showcased his technical acumen by co-developing 'Netfixxed' at PennApps Fall 2013, a project that won 'Best Use of Mashery APIs' by enhancing Netflix functionality with global content aggregation, Rotten Tomatoes integration, and social viewing features. devpost+1
Work
Education
Projects
Writing
How Clara suggests times
November 1, 2017A detailed Medium post explaining the supervised human-in-the-loop system Clara uses to algorithmically suggest and confirm meeting times, outlining the process from candidate generation to scoring and human review.
Clara understands your inner circle
July 1, 2016This Medium post, written while at Clara Labs, discusses a new feature allowing Clara to work more seamlessly with pre-approved contacts for scheduling.
Hobbies
Matthew enjoys outdoors, adventure, bikepacking, backpacking, and rafting. zola
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