Building an Operator CFO Mindset with Robert Checchia

What does it take to become the kind of CFO who can turn fast growth into disciplined, sustainable progress? Want more insights from finance leaders? Subscribe to Progressive Finance, Soldo’s new newsletter featuring practical leadership insights, finance trends, and conversations with CFOs and industry experts: https://substack.com/@progressivefinance Is there someone you’d like to see on The CFO Playbook? Email us at: **pr@soldo.com** In this episode of The CFO Playbook, David McClelland is joined by Robert Checchia, CFO at Benzinga. Robert shares his perspective on the modern CFO as an operator: someone who gets close to the business, understands how teams work, and helps turn an ambitious growth plan into clear priorities, accountable ownership and sustainable margins. Drawing on his experience across banking, consulting, private equity and operating roles, he explains why the best finance leaders are not gatekeepers—they empower others to make better decisions. In his conversation with David, Robert explores the discipline required to scale a business under private-equity ownership. He discusses how to distinguish good opportunities from the few that deserve real investment, how to give P&L owners meaningful visibility into their numbers, and why finance must connect revenue growth to margin, cash generation and execution. Robert also reflects on building a career across countries and industries, the importance of making decisions with imperfect information, and why leaders must own the consequences of their recommendations. He shares practical advice on using AI to improve productivity without losing human judgement, including how to encourage experimentation while maintaining effective guardrails. In this episode, you’ll learn: - Why the strongest CFOs are operators, not just financial stewards - How to say no to good opportunities so you can focus on the best ones - How to empower P&L owners with clear, consistent financial information - Why revenue growth must be measured alongside margin and cash generation - How to make decisions confidently with imperfect information - The value of accountability, ethics and clear communication in leadership - How to build incentives that align teams around growth targets - How to introduce AI tools responsibly while protecting human judgement - Why career pivots can build resilience, perspective and better leadership