Early in his tenure at Docusign, CFO Blake Grayson identified lingering inefficiencies and moved quickly to act. By making difficult decisions within his first 90 days, he stabilized operations, reset cost discipline, and positioned the business for growth—reinforcing his belief that speed in tough moments preserves momentum and clarity. Now Watch Our Complete Episode Featuring […]
1176: From Signatures to Systems of Value | Blake Grayson, CFO, Docusign
Within his first 90 days at Docusign, Blake Grayson recognized the company needed to make difficult efficiency decisions following a post-COVID slowdown. Acting quickly, he partnered with leadership to address the issue, noting that “making the hard decision faster is way better than waiting,” Grayson tells us. That moment set the tone for how he…
Listen to the Episode Below (0:54:49)
1108: Building Value in a Disrupted Industry | Kent Hoskins, CFO, Concord
Back in the early 2000s, when a recruiter lined up Kent Hoskins for a finance interview at Boosey & Hawkes, he came prepared to discuss guitar manufacturing. Instead, the executive immediately began quizzing him on music royalties—the recruiter had apparently misunderstood the brief. Hoskins didn’t get the job—at first. But two days later, he got…
Listen to the Episode Below (1:03:52)
668: Investors Make Room for a Streaming SPAC | Jason Eustace, CFO, CuriosityStream
It was roughly 12 months ago that Jason Eustace was named CFO of CuriosityStream, an upstart streaming media company launched in 2015 by Discovery Channel founder John Hendricks. For Eustace, CuriosityStream represents something of a flashback career chapter, arguably having more in common with the first 10 years of his finance career than the past…
Listen to the Episode Below (00:32:04)
465: Catching the Next Wave, Again and Again | Steve Cakebread, CFO, Yext
A Humble Take on a Hall-of-Fame Career Yext CFO Steve Cakebread’s resume is extraordinary, given the preeminent companies he’s worked for (HP, Silicon Graphics, Autodesk, Salesforce.com, Pandora, and Yext), the new technology categories that he’s helped to bring to market, and the staggering growth that those organizations posted under his corporate-finance leadership. Cakebread joined Salesforce…
Listen to the Episode Below (00:49:22)




