How do you make bold strategic bets in a crowded, fast-moving market? 

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In this episode of The CFO Playbook, David McClelland is joined by Tom DiDesidero, CFO at SmartRecruiters, the hiring platform focused on making recruitment easier and more effective for enterprise customers. 

If you’re only watching the numbers, you’re already behind. Tom’s view is that the best finance leaders are deeply embedded in the business, close to the product, strategy, and the decisions that actually shape where a company goes. In practice, that means making uncomfortable calls and convincing teams that moving fast is possible, even when it doesn’t feel that way. 

Acquisitions are where this gets tested. Long before anyone signs anything, there’s a lot of unglamorous work: data, narrative, confidentiality, and helping people through the uncertainty of joining something much bigger than what they knew. 

Tom is equally direct about AI. The question isn’t whether to use it, it’s whether you’re using the time it frees up on anything worthwhile. Automate the low-value work, and do something better with what you get back. 

His CFO Playbook principle: move quickly, be decisive, communicate clearly, and keep repeating the why until people understand their role in it. 

The finance leader’s playbook for high-stakes change

For finance leaders, transformation, whether growth, restructuring, or acquisition, takes more than solid numbers. It takes focus, honesty, and a clear view of reality. Download The Finance Leader’s Playbook for High-Stakes Change for practical actions to help CFOs surface uncomfortable truths, get the data right, prioritise with discipline, and communicate through uncertainty in ways that keep teams focused and moving forward.

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