Andrea Chesleigh


Andrea Chesleigh

Chief Product Officer, Spresso

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Andrea is a results-driven Product leader with over 15 years of industry experience. With a passion for delivering delightful user experiences, she is relentless at launching new products at both small startups and Fortune 500 companies. Andrea began her professional career with Verizon, where she was responsible for leading the website's redesign from concept to launch. During her extensive career, she has held various Product leadership positions at companies like Time Warner Cable, Zappos, Rent the Runway, and One Kings Lane, gaining industry expertise across retail, eCommerce, and telecommunications. For each organization she leads, she is an instrumental player in helping achieve transformative success, from building a product roadmap to supporting the overall vision in order to ensure customer satisfaction. She has a strong understanding of technology and combines that with her business-oriented approach to deliver successful products. Today, she leads the company’s efforts at Boxed as their VP of Product. Parallel to her current position at Boxed, Andrea also co-leads the NYC chapter of Women in Product, a non-for-profit organization designed to connect and empower women product managers and leaders. She was inducted into Phi Beta Kappa and graduated summa cum laude from Hunter College with dual degrees in English and Art. Andrea is a truly powerful world-class speaker who strives to keep solving seemingly impossible challenges.

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