1141: The Long Game of Resilient Finance Leadership | Erik Wissig, CFO, SureCo

1141: The Long Game of Resilient Finance Leadership | Erik Wissig, CFO, SureCo

When Erik Wissig recalls his early years as a founder, one moment still stands out. The team had met its growth goals and earned their bonuses—but the company’s cash flow hadn’t caught up. “You need the cash to make those payments,” he tells us. That hard-won lesson reshaped how Wissig approached finance from that day forward: plan ahead, balance ambition with liquidity, and bring the wider leadership team into that awareness.

Before that turning point, Wissig had spent a decade in investment banking, advising hundreds of middle-market companies on transactions. Eventually, the advisor wanted to build. In 2013, he co-founded Hixme to give employers a new way to fund individual health insurance—an idea born from the Affordable Care Act’s reshaping of the market. When regulatory realities slowed progress, Wissig stayed the course. Hixme’s platform and team were acquired by SureCo in 2020, where he now serves as CFO and COO.

At SureCo, Wissig’s banking discipline meets an operator’s pragmatism. He focuses on two levers—raising revenue per customer and scaling efficiencies—and on hiring into his weaknesses, surrounding himself with strong CPAs. His leadership style mirrors his philosophy on failure: persistence is progress. “If the game is still being played, then you haven’t failed,” he tells us.

Twelve years into his pursuit of the ICHRA model, Wissig remains motivated by one conviction: lasting change in healthcare begins by putting individuals—not institutions—at the center of the system.

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Episoder(1216)

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

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

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

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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 Sep 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...

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

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2 Sep 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 Aug 53min

1209: Finding a Larger Voice in the Room | Ross Grainger, CFO, Nasuni

1209: Finding a Larger Voice in the Room | Ross Grainger, CFO, Nasuni

Ross Grainger remembers an early chapter of his career when finance was only one part of the job.After stepping outside a traditional finance path to own and operate a Mako auto-body franchise, Graing...

26 Aug 33min

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

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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 p...

23 Aug 46min

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