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Andrea Chesleigh has an extensive work experience in senior leadership roles in product management and engineering. Andrea currently serves as the Chief Product Officer at Spresso, where they started in April 2023. Prior to this, Andrea was a Fellow at Primary Venture Partners and On Deck, both in 2021 and 2020 respectively. Andrea was also a Founding Member at Chief in 2019.

In terms of their previous roles, Andrea held multiple positions at Boxed, starting as the VP of Product in January 2019 and then becoming the SVP of Product from April 2022 to April 2023. Before that, they were the VP of Product and Engineering at One Kings Lane from April 2016 to January 2019, where they oversaw the successful replatforming and integration of the company into Bed Bath and Beyond.

Prior to One Kings Lane, Andrea was the Director of Product at IfOnly from April 2015 to April 2016 and the Director of Product, Retail at Rent The Runway from November 2013 to April 2015. Andrea also worked as a Senior Product Manager at Zappos Family of Companies from May 2012 to October 2013 and as a Senior Product Manager at Time Warner Cable from June 2009 to May 2012.

Andrea's work experience demonstrates their expertise in product management, UX design, site merchandising, engineering, and successful organizational transformations.

Andrea Chesleigh holds a Bachelor of Arts degree in English, Fine Art, and Special Honors Curriculum from Hunter College. Andrea also pursued Master of Fine Arts coursework in Drawing and Painting at the Academy of Art University. Additionally, Andrea completed Bachelor of Science coursework at Columbia University. Andrea has obtained certifications as a Certified Scrum Product Owner from Conscires Agile Practices and as a Certified Usability Analyst from Human Factors International.