1208: Quality, Trust, and Scale | Cal Brouilette, CFO, Flatiron Health

1208: Quality, Trust, and Scale | Cal Brouilette, CFO, Flatiron Health

Cal Brouilette recalls a sleepless night in Houston, speaking at 3 a.m. with someone from Blackstone about a purchase-and-sale agreement and transition-service agreements. It concerned a power-plant portfolio sale at Direct Energy, a Centrica subsidiary, that Brouilette places in 2013.

According to Brouilette, the assignment arrived in late September, when the CEO wanted the portfolio sold and announced before year-end. That left at most 120 days. Brouilette says he was managing finance and accounting, functioning as a business-unit CFO and loading up on MBA classes at Rice because his job had seemed stable.

The new assignment changed that calculation. Brouilette says he ran its finance work “soup to nuts,” covering the valuation taken into negotiations, management presentations, purchase-and-sale terms, and transition-service agreements.

The transaction presented him with what Brouilette describes as a $700 million “go or no go” decision. “Yes, this was hard,” he recalls thinking, but the experience prompted this realization: “I can do this job. I can make these decisions.”

Brouilette says the moment gave him confidence to make high-stakes decisions quickly while recognizing that he could “still keep learning.” He describes it as his shift from operator to strategist.

At Flatiron Health, Brouilette says his focus as CFO is not to “make a decision and let it ride,” but to consistently track results before the organization travels too far down “the wrong path.”

His remarks present strategic confidence not as certainty, but as the discipline to decide, keep learning, measure results, and correct course.

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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

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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

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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...

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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...

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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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