Cynthia Gaylor is likely to make a tech company extremely happy in the near future. Gaylor recently announced that her time has come to an end at DocuSign, a contract software giant with over a billion global users who rely on the company's platform to sign electronically – and thus accelerate the process of doing business.
Gaylor, who has been with DocuSign for more than 4 years, announced in March 2023 that she would be stepping down from her current role as Chief Financial Officer in the coming months. The news of her impending departure probably comes as a major blow to many DocuSign insiders, who have undoubtedly come to rely on the executive's wide-ranging influence and expertise.
Appointed DocuSign CFO in September 2020, Gaylor has since led a global team, making her responsible for strategic finance, corporate finance, FP&A, accounting, tax, treasury, revenue operations, corporate development and ventures, investor relations, internal audit, business process, and workplace experience. Prior to her CFO position, she also served on the Board of Directors at DocuSign and Chair of the Audit Committee.
DocuSign Chief Executive Officer, Allan Thygesen, was emphatic about Gaylor's impact on the electronic signature company, saying, “Cynthia has been an instrumental part of DocuSign's story. We have benefited from her unwavering commitment and leadership these last few years, and we are grateful for the strong foundation she leaves behind. Her countless contributions include guiding the company through tremendous growth and serving as a stabilizing force...”
Before moving up the ranks at DocuSign, Gaylor had already established herself as a proven leader in the industry, with more than 25 years of experience operating, scaling, and advising some of the largest tech and financial companies in the world. She most recently served as CFO for Pivotal Software, where she was in charge of leading the global finance and operations teams. In addition, while at Pivotal, she played an instrumental role in preparing the company to go public, leading its IPO and ultimately leading the sale of the company to VmWare.
Before joining Pivotal, Gaylor led corporate development at Twitter and prior to that was a managing director in Morgan Stanley’s technology group. She also served as a Vice President at JPMorgan Chase, where she focused on technology investment banking. In terms of education, Gaylor holds a Bachelor of Science in economics from the prestigious Wharton School at the University of Pennsylvania.