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DocuSign’s CFO sees ‘green field opportunity’

June 15, 2021, 9:00 AM UTC

Good morning,

“We find that once people move from pen and paper to online and automated ways of agreeing, they don’t move back,” says DocuSign CFO Cynthia Gaylor. 

Portrait of Docusign CFO Cynthis Gaylor
DocuSign CFO Cynthia Gaylor.
Courtesy of DocuSign

The San Francisco-based tech company that offers organizations an eSignature solution and trades under the ticker DOCU had a strong first quarter of 2021. Revenue for DocuSign was $469.1 million, an increase of 58% year-over-year, and the company reached a milestone of 1 million subscribers. Its annual revenue was $974 million in 2020. “We’re seeing strong customer demand and usage of our products that’s really helping drive our top line growth,” Gaylor says. 

eSignature is one way DocuSign is helping drive what it calls the “anywhere economy,” where agreements and work can be completed from any location, she explains.

“We’re in a very nascent space, where there’s lots of green field opportunity,” she says, adding that the company is seeing strong ROI across product categories. One metric she scrutinizes is “net retention rate,” which measures how customers who have been on the platform for at least a year are using DocuSign’s products, and “if they are growing their dollar net retention rate with us,” Gaylor says. “We had a net retention rate of 125% this past quarter, which was a historical high for us as a company,” she says. 

In an era of cyberthreats, within Gaylor’s teams across finance and operations, cybersecurity is “really embedded in all the back-office processes and operations used to support the company, particularly as we’re growing so quickly,” she says; and best practices also require collaboration between departments. 

“We’ve made investments, and we’ve hired some senior leaders across the company, in all of our departments, that focus on security,” she says. “Not only do we have a [chief trust and security officer], but we also recently hired a new CIO [chief information officer]. Within our product teams, security is very important.”

Gaylor didn’t take the traditional path to the CFO role. “I focused my entire career, over 25 years, in software and internet,” she says.

Gaylor started out her career as an investment banker in the technology sector for 18 years, served as head of corporate development at Twitter, and then began a practice as an advisor to “CEOs, CFOs, and boards, across their most strategic imperatives.” She went from advising the C-suite to becoming a CFO at two different companies. 

“I was on the board of DocuSign for a couple years before becoming the CFO, and I was chair of the audit committee,” she says. Beginning the role of CFO in September 2020 provided the opportunity to “really partner with our CEO, the rest of the management team, and the board from a different lens, and really help operationalize the tremendous growth we were seeing at scale as a company,” Gaylor says. 

See you tomorrow.

Sheryl Estrada

Big deal

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Going deeper

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