Why Operational CFOs Win: Strategy, Speed, and Leading Through Change with SmartRecruiters' Tom DiDesidero
The CFO PlaybookShow Notes
How does a CFO help a business stand out in a crowded market, execute a bold AI strategy, and lead the company through acquisition without losing focus?
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.
Tom explains why the most effective CFOs are deeply operational, not just financial stewards. He reflects on joining SmartRecruiters at a pivotal moment, partnering closely with CEO Rebecca Carr, and helping the company sharpen its strategy in an increasingly commoditised HR tech market. That meant narrowing the product focus, moving decisively on AI, and building belief across the organisation that the business could move faster than bigger competitors.
Tom shares how SmartRecruiters differentiated itself by simplifying its offering and investing in an AI-powered platform, including its agentic system, Winston. He discusses the importance of making bold decisions early, aligning teams around a clear direction, and turning strategy into execution through disciplined sequencing, milestones, and focus.
The conversation also explores what SAP saw in SmartRecruiters, and what it really takes to prepare a company for acquisition. Tom breaks down the finance leader’s role before, during, and after a deal: getting the data right, creating a credible story, managing confidentiality tightly, supporting teams through uncertainty, and adapting from a fast-moving independent company into a much larger, more matrixed organisation.
Tom also reflects on his wider career journey across software, e-commerce, payments, IPO environments, and transformation moments, and shares his view on AI in finance: use it to automate lower-value work, free up time, and help teams focus on better decisions and more valuable analysis.
Tom’s CFO Playbook principle: move quickly, be decisive, communicate clearly, and keep repeating the why until people understand their role in it.
Useful Links 🔗
SmartRecruiters - https://www.smartrecruiters.com
Tom Di Desidero - https://www.linkedin.com/in/thomasdidesidero/
About The CFO Playbook
The CFO Playbook is hosted by David McClelland, exploring how world-class finance leaders use technology, set goals, plan, lead teams, and drive growth.
Brought to you by Soldo.
More from The CFO Playbook
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
What does it take to become the kind of CFO who can lead through hypergrowth, change and uncertainty?
Is the future of finance full-time? Or are the best CFOs increasingly working across multiple businesses?
How do you lead finance in a global human rights organisation, protect independence, and make sure every pound supports the mission? Is there someone you’d like to see on The CFO Playbook? Email us at: [email protected] In this episode of The CFO Playbook, David McClelland is joined by Rohan Hewavisenti, CFO at Amnesty International, one of the world’s most recognised human rights organisations. Rohan shares what financial discipline looks like when the stakes are not measured in profit, but in people’s lives. He explains how Amnesty International’s International Secretariat operates as a £100 million organisation, working as part of a wider €400 million global movement, and why preserving independence shapes everything from funding decisions to resource allocation. In his conversation with David McClelland, Rohan reflects on his career across the not-for-profit sector, from ActionAid and Breast Cancer Care to the British Red Cross, RNIB and Amnesty International. He discusses managing volatility, rebuilding from a £20 million deficit, investing in future areas of human rights work, and keeping finance closely connected to mission impact. Rohan also explores the role of generative AI in a human rights organisation, from the ethical questions around bias, data, and autonomous weapons to the internal opportunities for improving efficiency and accessing decades of research. He explains why CFOs need to understand the cost of AI, build data skills across their teams, and stay open to technology by using it regularly. Rohan’s CFO Playbook principle: Understand the organisation deeply, from what drives income and costs to what drives good performance in mission-related work.
How do you rebuild a heritage automotive brand, manage risk through volatility, and keep finance close to the factory floor?