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.