1,031: Unlocking Operational Scale in Health Insurance Through AI and Data | Scott Blackley, CFO, Oscar Health

1,031: Unlocking Operational Scale in Health Insurance Through AI and Data | Scott Blackley, CFO, Oscar Health

When Scott Blackley was asked in kindergarten what he wanted to be when he grew up, his answer was surprisingly clear: “I want to be an auditor.” This early ambition was no coincidence; his father was a partner at KPMG, and young Blackley grew up around the firm’s offices, imagining himself one day sitting at a big desk, overseeing important work. True to his dream, he eventually ended up following in his father’s footsteps to become a partner at KPMG and invest a dozen career years there.

Despite achieving his childhood goal and carrying on the family legacy, though, Blackley eventually found himself at a crossroads. “It was a tough decision to leave KPMG,” he recalls, “but some of the experiences that I had had involving other people’s business problems had made me want to own them.” This realization marked a turning point in his career that fueled his desire to take on more responsibility and solve problems on a firsthand basis.

This drive led Blackley to Oscar Health, where he stepped into the CFO role during a pivotal moment. Reflecting on his early days at the company, Blackley observes, “When I joined, one of the things that I walked in the door with was a commitment to myself that I was going to be thoughtful about taking the time to understand the situation and then decisive about making decisions.” Consequently, within 90 days, he would end up reorganizing the finance function to separate FP&A from the controller’s office and hiring a new leader to build a more structured finance organization—one capable of supporting Oscar Health’s ambitious plans for growth and transformation.

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

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

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...

20 Syys 49min

When AI Changes the EPM Decision | David Den Boer, CEO, Column5 Consulting

When AI Changes the EPM Decision | David Den Boer, CEO, Column5 Consulting

AI is rapidly changing not only what finance technology can do, but how CFOs should think about the technology stack itself.In this bonus episode of CFO Thought Leader, David Den Boer, CEO of Column F...

18 Syys 28min

1215: Building Finance for the Long Game | Jessica Somers, CFO, Aledade

1215: Building Finance for the Long Game | Jessica Somers, CFO, Aledade

At Aledade, CFO Jessica Somers is helping finance navigate a business where investment decisions can take years to fully reveal their value.The technology-driven, physician-led company works with more...

16 Syys 49min

1214: The CFO Checklist Keeps Growing | Jack Gordon, CFO, Harri

1214: The CFO Checklist Keeps Growing | Jack Gordon, CFO, Harri

For Jack Gordon, the CFO role at Harri increasingly extends beyond finance—and into the mechanics of how an AI-powered business scales.Harri, a workforce operating system focused on hospitality, has e...

13 Syys 56min

1213: When Constructive Tension Yields Sharper Decisions | Martin Uhrik, CFO, Third Bridge

1213: When Constructive Tension Yields Sharper Decisions | Martin Uhrik, CFO, Third Bridge

When Martin Uhrik compared the margins of two visual-effects brands at Technicolor, one appeared far more profitable than the other. Uhrik tells us the reported difference prompted him to investigate....

9 Syys 54min

1212: When Working Capital Rewrites the CFO Agenda | Dan Barzily, CFO, Tipalti

1212: When Working Capital Rewrites the CFO Agenda | Dan Barzily, CFO, Tipalti

Shortly after Dan Barzily became CFO of Tipalti, a go-to-market transformation altered the company’s working-capital profile. One quarter later, Barzily tells us, the company missed its forecast acros...

6 Syys 36min

1211: Mission, Means, and the Will to Grow | Jonathan Ma, CFO, Sutter Health

1211: Mission, Means, and the Will to Grow | Jonathan Ma, CFO, Sutter Health

Jonathan Ma recalls being at his parents’ home in Nebraska one Saturday when his Morgan Stanley boss called with advice: pursue an opportunity at Sutter Health. After nearly 15 years, the mentor belie...

2 Syys 39min

1210: The Best Trade May Be the One You Don’t Make | Shiv Verma, CFO, Robinhood

1210: The Best Trade May Be the One You Don’t Make | Shiv Verma, CFO, Robinhood

Six weeks before Lehman Brothers went under, Shiv Verma tells us, he joined a hedge fund as the world felt like it was falling apart. After building structured-credit and CLO models at J.P. Morgan fro...

30 Elo 53min

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