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Crosby Sampson has a diverse work experience. Crosby started their career at Northern Buoy Accessories in 2012 as a Co-Founder and Owner, where they developed a line of nautical watches. In 2013, they joined Deloitte's Premier Student Program. Later in 2013, they joined Piper Sandler, initially as an Intern in Equity Sales & Trading. Crosby then progressed to the role of Analyst in Healthcare Investment Banking, followed by Assistant Vice President in Equities Business Strategy & Corp. Dev. Currently, they are serving as the Vice President in the same department at Piper Sandler.

Crosby Sampson has a Bachelor of Science in Business degree with a focus on Finance and Accounting from the University of Minnesota - Carlson School of Management. Additionally, they have attended the MIT Sloan School of Management for MIT Sloan Executive Education in the field of Blockchain Technologies. Furthermore, Crosby has obtained certifications in Blockchain Technologies: Business Innovation and Application from the Massachusetts Institute of Technology in September 2021, as well as Series 7 & Series 63 certifications from the Financial Industry Regulatory Authority (FINRA) in March 2017.