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Samantha Winkler has had a diverse range of work experience. Samantha started their career as a Summer Investment Analyst at Anson Funds in 2011. Samantha then worked as a Senior Analyst at Cornerstone Research from 2012 to 2014. In 2015, Samantha joined Citi as an Investment Banking Analyst. Samantha then transitioned to Munchery, where they worked in Strategic Finance from 2016 to 2017. Samantha then joined Stitch Fix as part of the Strategic Finance and Investor Relations team from 2017 to 2020. Currently, they are at PEAK6, where they started as the Vice President of Strategic Capital in 2020 and later became the Principal of Strategic Capital in 2022.

Samantha Winkler completed their HBA degree in Finance, Strategy, and Economics at the Ivey Business School at Western University from 2008 to 2012.