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Brett Chereskin has a diverse range of work experience spanning various industries. In their current role as the Chief Operating Officer at dub, they hold a senior leadership position responsible for overseeing the company's operations.

Prior to their current role, Brett served as a Limited Partner at both Stage 2 Capital and Context VC in 2022 and 2021 respectively. These roles involved participating as an investor and providing strategic guidance to the companies.

In 2020, Brett worked as an Angel Investor at Truv, where they likely invested in early-stage startups and provided mentorship and support.

Before their venture into the investment field, Brett gained extensive experience at Affirm, Inc. Brett held several positions, including Head of Business Operations, Chief of Staff to the Chief Commercial Officer, Business Development Operations, and Diversity and Inclusion Project Manager. In these roles, they played a crucial role in developing and implementing frameworks, building business strategies, and operationalizing market expansion and growth.

Brett's earlier career was in the US Army, where they served for over a decade. Brett held various leadership roles, such as Senior Director/Deputy Department Chair, Senior Director/Company Commander, Fellow/Military Intelligence Officer, and Director/Company Commander. These positions showcased their expertise in training and mentoring cadets, planning and resourcing organizations, and managing operational sites across different locations.

Overall, Brett Chereskin's work experience demonstrates their strong leadership, strategic thinking, and operational skills across various industries.

Brett Chereskin holds a Bachelor of Science (BS) degree in Environmental Geography with a minor in Environmental Engineering from the United States Military Academy at West Point, which they completed from 2002 to 2006. Brett later pursued further education at Embry-Riddle Aeronautical University, earning a Master of Science (MS) degree in Unmanned Systems with a track in UAS between 2015 and 2017. In addition to their degrees, Brett Chereskin has obtained certifications from the Federal Aviation Administration. Brett holds Commercial Pilots Licenses for fixed-wing and rotary-wing aircraft, which they acquired in June 2008, and they also possess a Remote Pilot Licence obtained in June 2017.