Docusign CFO lays out the company’s plans for a resurgence

Docusign may not be the first company that springs to mind when you think “innovation.” Digital signatures, the company’s core service, have been legally binding since the Clinton administration.

For many, they’re indelibly associated with the shift to remote work accelerated by the pandemic. As former Docusign CEO Dan Springer declared in 2022, in remarks that almost sound quaint, “As people begin to return to the office, they are not returning to paper.”

But Docusign hasn’t stayed on the sidelines during the AI boom. In fact, an AI offering—known as Intelligent Agreement Management or IAM—is key to its plans for a resurgence, CFO Blake Grayson told CFO Brew. “We think that’s our path to future growth,” he said.

Boom and bust. Docusign’s trajectory in the 2020s resembles that of many tech companies. During and after the pandemic, Docusign boomed as businesses adopted remote work, and thus, remote document signing. Its revenues more than doubled between fiscal years 2020 and 2022, from $974 million to $2.1 billion. It went on a hiring spree in those years, increasing its headcount from 3,909 to 7,461.

Then came the slowdown. In FY 2023, Docusign’s revenues grew by a comparatively meager 19%, and by a still-more-sluggish 10% in FY 2024. Between September 2022 and February 2024, Docusign went through three rounds of “restructuring,” laying off from 6% to 10% of its workforce each time. The reorganizations “were tough decisions, but decisions that we needed to make as a company,” Grayson said.

Now, Docusign is counting on AI to help it emerge from the trough. The company chose to prioritize research and development during the restructurings, mostly to support the development of IAM, Grayson said.

In some ways, IAM is a natural extension of what Docusign already offers. It can help address some of the biggest problems customers have with contracts: the sheer amount of data they create. “The average customer in IAM for us right now has over 5,000 agreements,” Grayson pointed out, and he noted that this data is often scattered throughout an organization, a phenomenon he likens to “digital filing cabinets.”

“If you have a couple hundred employees, they can’t tell where things are,” he said.“How do you track the value you have, and are you getting fair treatment for those contracts?”

IAM addresses that issue by automatically putting signed contracts into an “intelligent repository…You can search it. You can find related contracts. There’s all these insights you can pull from it,” Grayson said. A feature called Agreement Desk allows users to track the process of a contract from start to finish so they understand when negotiations happened and why.

“It’s still early days” for IAM, which launched to commercial customers in North America about 18 months ago, Grayson said. IAM represented 10.8% of Docusign’s annual recurring revenue in fiscal 2026, up from 2.3% in 2025. The company had 102% dollar net retention coming out of FY 2026, Grayson said, due to both the IAM expansion and “doing a better job retaining our customers.”

Getting to the conflict. Grayson drew upon his past experience while helping to bring IAM to fruition. He came to Docusign in 2023 after more than ten years in finance at Amazon, and after serving as CFO at digital advertising platform The Trade Desk for three and a half years, from 2019 to 2023. In the latter role, he said, he and his team witnessed the rise of streaming and saw that providers would likely incorporate ads, a trend they were able to take advantage of. “I learned from that about trying to think down the road,” he said.

CFOs, he believes, shouldn’t shy away from difficult conversations. Staff are always ready to talk about what’s going well, he said, but “what I learned from Amazon was, you talk about that for about 30 seconds,” and then focus on what’s causing friction. “I want to get to [the conflict] straight away because these folks know the business, hopefully, better than I do. So what I tend to push on is ‘What’s the controversy?’”

Being forthcoming about pain points, he said, enables teams to make choices. “If you can make one hard decision every day, that’s super valuable, as long as your judgment’s good,” he said.