1185: Scaling Smarter in the AI Era | Sarah Riley, CFO, dbt Labs

1185: Scaling Smarter in the AI Era | Sarah Riley, CFO, dbt Labs

When the pandemic began reshaping the world in early 2020, Sarah Riley was helping guide finance at Zoom through an unprecedented surge in demand. “You could see the volume of Zoom almost spiking up by the regions that were going into shutdown,” Riley tells us. What followed was unlike anything most software companies had experienced before. During her four years at Zoom, the company expanded from roughly $200 million in ARR to $4 billion, Riley tells us. At one point, Zoom spent nearly half a billion dollars on AWS infrastructure costs it had not anticipated, she explains.

For Riley, the experience fundamentally reshaped how she viewed finance leadership. Rather than becoming fixated on gross margin guidance or traditional planning cycles, she says the finance team had to continually reevaluate the “strategic heart” of the business as Zoom evolved from an enterprise software company into a platform supporting schools, consumers, and businesses worldwide. “Forecasting and discipline comes second” in moments of extraordinary change, Riley tells us.

That mindset now informs her role as CFO of dbt Labs, where she oversees finance, accounting, and data operations while helping guide the company through its merger with Fivetran. Riley says today’s defining challenge for software businesses is balancing legacy operating models with the realities of AI-driven transformation. “You need to balance that with how do we make sure that we’re investing aggressively enough in capturing what our user base is turning into,” she tells us.

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1221: Rebuilding Bread Financial’s Capital Foundation—And What It Made Possible | Perry Beberman, CFO, Bread Financial

1221: Rebuilding Bread Financial’s Capital Foundation—And What It Made Possible | Perry Beberman, CFO, Bread Financial

When Perry Beberman arrived at what is now Bread Financial, the company had a balance sheet problem. It was carrying too much leverage, had insufficient capital, and needed a more disciplined approach...

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1220: At Hippo, Growth and Risk Work Together | Guy Zeltser, CFO, Hippo Insurance

1220: At Hippo, Growth and Risk Work Together | Guy Zeltser, CFO, Hippo Insurance

In 2023, Hippo faced what CFO Guy Zeltser describes as perhaps the worst quarter in the insurance company’s history. The response was not to chase growth harder. Instead, leadership made a decision th...

11 Loka 47min

The New Economics of Revenue | Sam Chung, Chief Customer Officer, Salesforce

The New Economics of Revenue | Sam Chung, Chief Customer Officer, Salesforce

How consumption models, AI, and rising complexity are reshaping the CFO mandateRevenue models are becoming more complex—and for finance leaders, the consequences extend well beyond how a company bills...

7 Loka 50min

2019: Building a Health Plan Around What People Actually Do | Tami Wilson-Ciranna. CFO, Curative

2019: Building a Health Plan Around What People Actually Do | Tami Wilson-Ciranna. CFO, Curative

When Tami Wilson-Ciranna joined Curative in April 2020, the assignment came with what now looks like a spectacularly optimistic assumption: three months.“I met with Fred on a Tuesday and I started on ...

4 Loka 48min

1218: Why Pegasystems Is Betting on Work, Not Tokens | Ken Stillwell, CFO, Pegasystems

1218: Why Pegasystems Is Betting on Work, Not Tokens | Ken Stillwell, CFO, Pegasystems

When Pegasystems began building its cloud business, the economics were hardly what investors would expect from a mature software company. Cloud gross margin was below 30%, recalls CFO and COO Ken Stil...

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2017: A Sharper Portfolio, A Clearer Capital Story | Brittany Cerwin, CFO, Middleby Corporation

2017: A Sharper Portfolio, A Clearer Capital Story | Brittany Cerwin, CFO, Middleby Corporation

For years, Middleby executives arriving at investor conferences faced a storytelling problem: 30 minutes wasn’t much time to explain three different businesses, each with its own brands, markets, inve...

27 Syys 41min

People and Places: The Geography of a CFO Career

People and Places: The Geography of a CFO Career

CFO careers are often described through titles, companies, and accomplishments. But another force can quietly shape the journey: place.In this themed episode of CFO Thought Leader, five finance leader...

23 Syys 37min

2016: Building the Operating System for Agentic Automation | Ryan Roccon, CFO, Zapier

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At Zapier, the rise of AI is changing more than the automation products customers build. It is reshaping how the company organizes, invests, prices its offerings, and thinks about its next stage of gr...

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