Cynthia Gaylor Company: Pivotal

Cynthia Gaylor

Finalist for Transformation Agent

Cynthia Gaylor is Pivotal’s Chief Financial Officer, responsible for leading the company’s worldwide Finance and Operations organizations— including financial planning and analysis, accounting, treasury, tax, corporate development, sales and services operations, investor relations, and brand and real estate.

Cynthia joined Pivotal in June 2016 and has been instrumental in the company’s transformation from a venture-backed startup generating $250 million in revenue to a publicly-traded company generating over $650 million in revenue with a market cap over $5 billion. She played a key role in transitioning the company to a subscription model; led the IPO process; overhauled the finance and operational systems; developed, recruited, and diversified her team; put in place a working capital line to fund the company to IPO; and built out the capabilities required to be a sustainable public company.

Cynthia has spent her entire career in the technology sector, specializing in software, internet, mobile, ecommerce, and payments, with a particular focus on advising CEOs and boards on their most strategic growth imperatives— including transformational financings, joint ventures, and mergers and acquisitions. She spent more than 17 years as a technology investment banker, most recently as a Managing Director at Morgan Stanley. She has also worked with industry-leading companies— like Workday, Splunk, Palo Alto Networks, facebook, LinkedIn, Netflix, Amazon, Google, eBay, Hyperion Software, VeriSign, Zappos, Admob, Websense, and Intuit, among others.

Prior to joining Pivotal, Cynthia was the Head of Corporate Development and an Advisor at Twitter, where she scaled the team, and led the company through an intensive period of M&A activity.

Cynthia earned a bachelor’s degree in Economics from the Wharton School at the University of Pennsylvania. She is on the boards of DocuSign— a public company that helps organizations connect and automate how they prepare, sign, act on, and manage agreements— Girls on the Run Bay Area— a non-profit that helps girls become their best selves— and the Junior Committee League for the San Francisco Symphony— a non-profit dedicated to funding music programs in San Francisco public schools.