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Andrea Chesleigh
COO @ Spresso.AI | Transformational Product Leader | Driving Innovation in Ecommerce
Professional Background
Andrea Chesleigh is a dynamic professional currently serving as the Chief Operating Officer at Spresso, a distinguished provider of AI-powered solutions designed specifically for ecommerce businesses. With over two decades of rich experience, she has made her mark at several prestigious companies including Verizon, Zappos, Rent the Runway, and One Kings Lane/Bed Bath and Beyond. Her career reflects a robust commitment to excellence as well as a profound understanding of the intersection between technology and consumer engagement.
Andrea's approach to product leadership is grounded in data-driven and customer-centric principles, showcasing her ability to blend analytics with empathy for users. She has a remarkable history of facilitating substantial business growth through innovative strategies and effective management. Her prowess isn't just limited to launching new products; she has successfully orchestrated the replatforming projects that have redefined market strategies and significantly improved operational efficiencies.
Education and Achievements
Andrea's educational journey is as impressive as her professional endeavors. She holds a Bachelor of Arts in English and Fine Art, where she excelled in a Special Honors Curriculum at Hunter College. Additionally, she has pursued Master of Fine Arts coursework focused on Drawing and Painting at the Academy of Art University, further enhancing her creative flair and artistic sensibility. She also has exposure to the Bachelor of Science coursework at Columbia University, laying a strong foundation in analytical thinking and problem-solving.
Beyond her academic credentials, Andrea has been recognized for her extraordinary contributions to the industry. As a Council Member for Women in Product's Executive Edge Program, she mentors the next generation of aspiring leaders, fostering an inclusive environment that champions diversity in the tech space. Furthermore, her prior role as co-lead for the NYC chapter of Women in Product allowed her to promote executive leadership and support women in their career journeys through various speaking engagements and initiatives.
Achievements
Andrea's significant achievements extend beyond her formal roles. She is a respected figure in various venture networks where her strategic insights have earned her fellowships, further contributing to her reputation as a pioneer in product innovation. Her leadership style has not only driven teams towards achieving corporate goals but has also instilled a culture of empowerment and motivation among her colleagues.
In her capacity as Chief Operating Officer at Spresso.AI, she has steered the company towards unprecedented growth, implementing AI technologies that reshaped the ecommerce landscape. Her previous role as Chief Product Officer also underlines her versatility and expert knowledge in product management. As SVP and VP of Product at Boxed, she played an integral role in enhancing customer experiences and streamlining operational processes.
Her previous experience includes high-impact positions such as VP of Product and Engineering at One Kings Lane/Bed Bath and Beyond and Director of Product at IfOnly, showcasing her ability to transition across organizations while delivering exceptional results. In her earlier career, Andrea held significant roles including Senior Product Manager at both Zappos Family of Companies and Time Warner Cable, paving her way as a thought leader in the tech industry.
Andrea’s unique blend of creativity and analytical skills continues to set her apart in the competitive landscape of technology and ecommerce. Whether through her pioneering work at Spresso or her continuous advocacy for diversity in leadership, Andrea Chesleigh exemplifies a modern leader who is not only innovating in her field but also empowering others to reach their full potential.
