Getting Ready for the Future: Our Top 7 Digital Transformation Leadership Strategies

Most companies discuss digital transformation as if it were a mystical process that will magically resolve all their problems. The reality is messier. 

While executives throw around terms like “digital-first” and “omnichannel,” their organizations are often plagued by legacy systems, departmental silos, and a fundamental lack of people who understand how to lead through technological change. 

The problem isn’t technology—it’s leadership. After working with dozens of organizations struggling through digital transformations, it’s clear that success comes down to having the right people in the right roles, making tough decisions about outdated processes, and understanding what customers want rather than what the latest consultant deck promises. 

Stanton Chase knows this works. 

1. Stop Treating Digital Disruption Like a Buzzword

Every industry is being reshaped by AI, automation, and data analytics. That’s not news. What is notable is how many executives still discuss digital transformation without fully understanding its implications for their day-to-day operations. 

There is a massive gap between companies that worry about digital change and those that profit from it. KPMG’s 2024 Global Tech Report found that 78% of tech executives worry about keeping pace with change, while KPMG’s US Technology Survey shows 88% of executives report improved profitability from digital transformation—a jump from just 45% in 2023. 

When nearly 8 out of 10 executives are still stuck in worry mode while almost 9 out of 10 are seeing real profits, you know which group is treating this like a buzzword versus implementing change. The companies driving that profitability growth stopped using digital transformation as a conference room talking point and started using it to solve real business problems. 

Take retail, CPG, and D2C companies—they couldn’t afford to keep talking about digital transformation in PowerPoint decks because their customers had already moved online and weren’t coming back. They were forced to figure out what digital transformation meant for their operations, their supply chains, and their customer relationships. That’s why they’re leading the profitability gains now. 

2. E-Commerce Isn’t a Channel Anymore—It’s The Business

If you’re still thinking about e-commerce as one of several sales channels, you’re already behind. Amazon, Zalando, and Shopify haven’t just changed how people shop—they’ve changed what people expect from every business interaction. 

Those expectations mean you can’t just add an online store to your existing setup and call it digital transformation. Most companies are still trying to bolt digital commerce onto their existing business model, treating it like another distribution channel alongside retail stores or catalogues. But when customers expect Amazon-level convenience and personalization from every interaction, your entire business model needs to work differently. 

This reality explains why the best companies are rethinking not just how they sell, but where they sell. McKinsey research shows that 63% of leading companies are investing in social commerce, compared to just 50% of laggards, because they recognize that platforms like Instagram and TikTok aren’t just marketing channels—they’re where entire generations now discover and buy products. 

Companies that figure out how to sell where their customers already spend time will win. Those that don’t will keep wondering why their expensive digital marketing campaigns aren’t working. 

3. Hire Leaders Who Understand Technology

The biggest talent gap isn’t in software development or sales—it’s in leadership. KPMG’s Global Tech Report found that 80% of executives complain that senior leadership’s risk aversion makes their organization slower than competitors to embrace new technology. When 8 out of 10 executives are calling out their leaders for being too cautious, you know where the real bottleneck is. 

Here’s the thing about that risk aversion: most of it comes from not understanding what you’re risking. Executives who treat technology like some mysterious black box will always default to “let’s wait and see.” They’re not being cautious—they’re being ignorant. 

You need executives who can talk to both engineers and customers. Chief Digital Officers who understand business strategy. CMOs who can read data, not just creative briefs. CFOs who understand that technology investments often take time to show ROI, but when they do, the returns can be enormous. 

The best digital leaders combine technical knowledge with the ability to get entire organizations moving in the same direction. 

4. Fix Your Foundation First

Most digital transformation failures happen because companies try to build on broken foundations. KPMG’s US Technology Survey found that 58% of companies face weekly disruptions due to flaws in their legacy systems. 

Here’s what those broken foundations look like: You might be trying to build new digital capabilities on top of systems that barely work together. Maybe your CRM doesn’t sync with your e-commerce platform. Your inventory management system probably can’t talk to your marketing automation tools. Customer data likely lives in six different places with six different formats. 

This integration chaos is why most digital investments fail. PwC’s 2025 Digital Trends in Operations Survey confirms this: 92% say tech investments haven’t fully delivered expected results, with integration complexity cited by 47% of operations leaders as the biggest roadblock. 

So, before you hire another consultant or buy another software platform, fix these basic integration problems. Connect your existing systems. Clean up your data architecture. Build APIs that work. 

5. Gain Insights from Successful Companies

Unilever didn’t become a digital leader by accident. Neither did Nestlé nor Ahold Delhaize. They succeeded because they treated digital transformation as an integrated business strategy, not a technology project. 

What does that look like? Take Unilever’s approach to direct-to-consumer brands—they didn’t just build websites for existing products. They created entirely new business units that operated like digital startups, with different supply chains, marketing approaches, and customer relationships. Nestlé restructured their entire organization around consumer insights and data, not just product categories. Ahold Delhaize rebuilt its grocery operations from the ground up to compete with Amazon, treating online and offline as one unified experience. 

All of these companies changed how they operated at the most basic level. They broke down silos between departments so customer data could flow freely. They hired leaders who understood both technology and business operations. They made tough decisions to shut down legacy processes that couldn’t adapt to digital customer expectations. 

The lesson isn’t to copy exactly what they did—it’s to approach transformation with the same level of commitment to changing how your business works, not just adding technology on top of existing processes. 

6. Stanton Chase Understands Your Goals

Executive search has changed beyond just finding candidates with the right CV. The best search firms, like Stanton Chase, now help companies think through what digital leadership looks like in their specific context. 

The challenge is that most companies are taking the same approach to finding digital talent. PwC’s 2025 Digital Trends in Operations Survey found that 47% of companies rely on hiring skilled talent as their top approach to building a digital-ready workforce. But if everyone’s fishing in the same talent pool, you need search partners who can find the candidates others miss, let’s call them ‘hidden gems’. 

That means working with a search partner who understands organizational readiness, cultural fit, and long-term strategic alignment. The best search firms build leadership teams that understand technology, rather than just ‘filling’ top-level positions. 

7. Build Leadership Teams for the Long Term

Digital transformation isn’t a project with a beginning and an end. It’s the new normal. But most companies are still thinking about leadership development as if technology will slow down. 

The reality is the opposite. Deloitte’s latest CEO survey found that 89% of CEOs are exploring, piloting, or implementing agentic AI within their organizations, with one in ten planning to have at least one business function fully implemented by the end of the year. Technology adoption is accelerating faster than most leadership teams can handle. 

This acceleration means you can’t just hire your way out of digital skills gaps anymore. You need succession planning that accounts for technological change. Board education on digital trends. Internal development programs that create digitally fluent leaders at every level. The companies that do well over the next decade won’t be those with the fanciest technology—they’ll be those with leaders who can learn and make good decisions as technology continues to change. 

Making Digital Transformation Work

Digital transformation fails most often because companies treat it like a technology problem. They buy software, hire consultants, and expect results. But the technology is rarely the bottleneck. 

The real issue is usually much simpler: the people making decisions don’t understand how digital tools work in their business. They don’t know what customers want online. They can’t break down silos between departments. They’re afraid to change processes that have worked for decades. 

If you’re struggling with digital transformation, the problem probably isn’t your technology stack. It’s your leadership stack. Fix that first, and the rest becomes much easier. 

About the Authors

Kevin Bradbury is a Partner at Stanton Chase Amsterdam and Regional Practice Leader for Private Equity across EMEA. Since joining Stanton Chase in 2012, Kevin has specialized in executive search for technology companies, including SaaS/PaaS/IDaaS businesses, telecommunications platform providers, and technology consultancy firms. With two decades of experience in the technology search industry, Kevin has developed deep expertise in identifying and placing digital leaders who can drive transformation initiatives. He graduated with a B.A. in Law and Political Science from Carleton University in Ottawa, Canada, and holds certifications from Hogan Systems for Leadership Assessment and is a certified practitioner in Culture and Executive Search from Hofstede Insights, bringing both technical search expertise and cultural assessment capabilities to his work with technology leaders. 

Joost Leferink is a Partner at Stanton Chase Amsterdam with extensive experience as a former FMCG industry executive before transitioning to executive search. His operational background includes country and regional marketing, sales, operations, and general management roles, as well as global strategy and organizational transformation initiatives. This unique combination of hands-on business transformation experience and executive search expertise gives Joost particular insight into the challenges leaders face when driving digital change within established organizations. He holds an MBA from Canterbury Business School and completed the INSEAD High Impact Leadership Program, complementing his economics background from Tilburg University with advanced leadership development training.