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…
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Turning Finance Into An Unlocker | Aneal Vallurupalli, CFO, Drata
By tracing retention through 200 customer calls, onboarding flows, and product gaps, Vallurupalli realized the breakthrough wasn’t a single metric but the journey itself. His holistic diagnosis reframed retention as a system problem—shaping Airbase’s cross-functional fixes and guiding its existing-revenue engine through scale. Now Watch Our complete Episode Featuring CFO Aneal Vallurupalli of Drata In […]
1146: Building a Finance Org That Thinks Before It Counts | Aneal Vallurupalli, CFO, Drata
The morning after Airbase’s sale closed, Aneal Vallurupalli woke up to a very different org chart. Before the deal, roughly a third to almost half of the company reported to him, including onboarding, professional services, account management, customer success, and financial services revenue, he tells us. The day after, those teams rolled into the acquirer…
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The Power Behind Story-Driven Growth | David lee, CFO & COO, WEBTOON
During Best Buy’s Renew Blue turnaround, David Lee helped redirect over $1 billion in savings to reinvent stores as “omnichannel showrooms,” blending digital and in-store experiences. By aligning consumer insight with disciplined finance, the team defied predictions of retail decline—driving one of the fastest stock recoveries in the S&P 500. Now Watch the Complete Episode […]
Acquisitions As Customer Experience Strategy | Beth Gaspich, CFO, NiCE
Beth Gaspich recalls ringing the NYSE bell in 2008 as RiskMetrics went public amid extreme market volatility. After months of S-1 prep and roadshows, the decision to proceed came “down to the wire.” Executing successfully proved the value of preparation, decisive timing, and clear investor storytelling in uncertain markets. Now Watch our Complete Episode Featuring […]
1131: Building an AI-Ready Finance Engine | Beth Gaspich, CFO, NiCE
In 2008, Beth Gaspich stood on the floor of the New York Stock Exchange, ringing the bell as RiskMetrics went public. What made the moment extraordinary was its timing—amid one of the most volatile markets in decades. The IPO decision, she tells us, came “down to the wire.” After months of preparing the S-1, long…
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Scaling Finance for the Cloud-Native Era | David Obstler, CFO, Datadog
During post-COVID uncertainty, David Obstler spotted early signs of customer optimization and reprioritized Datadog’s investments. By pulling back selectively while sustaining rapid investment in key areas, he preserved profitability, avoided layoffs, and strengthened the company’s ability to reaccelerate growth—building long-term resilience without compromising culture. Now Watch the Complete Episode Featuring CFO David Obstler David Obstler […]
1130: Building Resilient Finance in Uncertain Times | David Obstler, CFO, Datadog
When David Obstler joined Datadog in 2018, the company’s co-founders had already built momentum with a product that observed modern cloud workloads. What struck Obstler was the alignment with a powerful long-term trend—the shift from legacy, on-premise systems to modern cloud applications. “It was a product that had a lot of product market fit in…
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1128: Capital Discipline in a Usage-Based World | Ben Gammell, President & CFO, Brex
In 2018, Brex made a defining decision: rather than rely on middleware providers like Stripe or Marqeta, it built its own payments infrastructure from the ground up. That move, Ben Gammell tells us, gave the company a direct integration with MasterCard and the ability to issue corporate cards in “over 50 plus local currencies.” The…
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1122: Capital Allocation as a CFO’s North Star | Chris Miorin, CFO, apexanalytix
Chris Miorin’s path to the CFO office began in a crucible of leadership. At West Point, and later at Ranger School, he was forged in environments designed to test resolve. Commissioned shortly after 9/11, he knew combat was certain. Leading an infantry platoon in Iraq, he found himself working side-by-side with a colonel “30 years…
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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…
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