When Jeff Epstein was CFO at Oracle during the 2008 financial crisis, his team had $10 billion in cash but couldn't borrow a billion in the commercial paper market. That experience, among others, shaped his perspective on how finance leaders should approach risk—both taking it and managing it.
Today, Jeff brings his risk management expertise to multiple roles: as an operating partner at Bessemer Venture Partners, board member at companies like Okta and Twilio, and trusted advisor to countless CFOs. In a landscape where finance leaders must balance AI investment enthusiasm with market uncertainty, his frameworks for evaluating risk feel particularly relevant.
Jeff sat down with Anrok co-founder and CEO Michelle Valentine to share his perspective on how modern CFOs can lead through uncertainty, what metrics actually matter for scaling companies, and why the best finance leaders know when to take calculated risks—and how to bring others along. ⊞
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