Business Digitalization Strategy: Where Most Companies Go Wrong

Business digitalization strategy is the process of embedding digital tools, data, and processes into the core of how a company operates and goes to market. Done well, it reshapes how you acquire customers, serve them, and retain them. Done badly, which is far more common, it becomes a long and expensive exercise in buying software that nobody uses.

The failure rate is not a technology problem. It is a strategy problem. Most companies digitalize the wrong things first, in the wrong order, for the wrong reasons.

I have watched this play out across dozens of client engagements over the years. A business comes in with a digitalization mandate from the board. They have budget, they have a vendor shortlist, and they have a PowerPoint with a transformation roadmap. What they rarely have is a clear answer to the question: what specific commercial outcome are we trying to improve, and how will we know if we have succeeded?

Why Digitalization Projects Stall Before They Deliver

The graveyard of failed digitalization projects has a common headstone. It usually reads something like: “We implemented the platform. Adoption was low. The business moved on.”

There are a few patterns I see repeatedly. The first is starting with the technology rather than the problem. A CRM gets purchased because a competitor has one, or because a consultant recommended it, not because there is a diagnosed gap in how customer relationships are currently managed. The second pattern is treating digitalization as a project with a start and end date, rather than a continuous capability that needs to be built and maintained.

The third pattern, and this one is underappreciated, is underestimating how much digitalization is a change management exercise. The technology is the easy part. Getting a 60-person sales team to change how they log customer interactions, or convincing a finance director that the attribution model they have used for eight years is no longer fit for purpose, that is where most transformations quietly die.

When I was running iProspect and we were growing the team from around 20 people to over 100, a significant part of that growth was built on our ability to use data infrastructure better than our competitors. Not fancier tools, just more disciplined use of the tools we had. We built reporting processes that gave clients a clearer picture of what was driving commercial outcomes, not just traffic or clicks. That clarity was a differentiator. It won pitches. The lesson was not about the technology. It was about having a point of view on what the data meant and being willing to act on it.

If you are thinking about digitalization in the context of your broader commercial strategy, the Go-To-Market and Growth Strategy hub covers the wider landscape of how marketing and business strategy connect, including how digital capability fits into a coherent growth model.

What a Digitalization Strategy Actually Needs to Cover

A proper digitalization strategy has four components that need to work together. Most companies only address two or three of them, which is why the results are partial at best.

1. Customer experience architecture

Start with how customers interact with your business today, across every touchpoint, and map where the friction is. Not where you think the friction is. Where customers actually drop off, disengage, or complain. This is where digitalization should begin, because it is where the commercial case is clearest.

BCG’s work on commercial transformation and growth strategy makes the point that the companies generating the most durable growth are those that connect customer experience improvements directly to revenue outcomes, rather than treating them as separate workstreams. That connection is what gives a digitalization project its commercial spine.

I have a strong view on this, shaped by years of watching marketing used as a blunt instrument to paper over product or service problems. If a company genuinely resolved every point of friction in the customer experience, a large portion of the marketing spend propping up retention and acquisition would become less necessary. Digitalization, done properly, is one of the few investments that can actually address root causes rather than symptoms.

2. Data infrastructure and ownership

This is the component that marketing leaders most often abdicate to the technology team, and it is a mistake. Data infrastructure is a commercial strategy decision. What data you collect, how it is structured, who owns it, and how it flows between systems determines what you can do commercially for the next five to ten years.

The companies that get this right treat their first-party data as a strategic asset, not a byproduct of running campaigns. They build data models that reflect how customers actually behave, not how the CRM vendor’s default setup assumes they behave. And they invest in the unglamorous work of data hygiene and governance, because bad data at scale is worse than no data at all.

Tools like Hotjar’s feedback and growth loop frameworks are useful here, not because they solve the data infrastructure problem, but because they surface the qualitative layer that quantitative data alone cannot give you. Understanding why customers behave as they do is as commercially important as knowing that they do.

3. Process redesign, not process digitisation

There is a critical distinction between digitalising an existing process and redesigning a process for a digital environment. Most companies do the former. They take a broken or inefficient process and put a digital layer on top of it. The result is a faster version of something that was already not working well.

Effective digitalization asks: if we were designing this process from scratch, knowing what digital tools make possible, what would it look like? That is a harder question to answer, and it usually involves some uncomfortable conversations about how the business currently operates. But it is the question that generates the real commercial return.

BCG’s research on scaling agile capabilities is relevant here. The organisations that build genuine digital capability are those that redesign how teams work, not just what tools they use. Agility is not a technology property. It is an organisational one.

4. Commercial measurement and feedback loops

A digitalization strategy without a measurement framework is a strategy without accountability. And measurement in this context does not mean tracking every metric the platform makes available. It means defining, in advance, what commercial outcomes you are trying to move, and building the reporting infrastructure to track them honestly.

I spent time judging the Effie Awards, which are specifically about marketing effectiveness, and one of the consistent patterns among the winning cases was the clarity of the commercial problem being solved. Not “we wanted to improve brand awareness.” Something specific: a defined customer segment, a measurable behaviour change, a revenue outcome with a number attached. Digitalization strategies need the same discipline.

The Sequencing Question Most Companies Get Wrong

One of the most consequential decisions in a digitalization strategy is sequencing. What do you do first, second, and third? Most companies sequence based on what is easiest to implement, or what the board is most excited about, or what the technology vendor recommends. None of these are the right basis for sequencing decisions.

The right sequencing logic is commercial impact relative to implementation complexity. You want to identify the initiatives that will generate measurable commercial return quickly, because early wins build organisational confidence and create budget for the harder, longer-term work. And you want to sequence the foundational infrastructure work, particularly data and integration, before you layer on the more visible customer-facing capabilities that depend on it.

The analogy I use with clients is plumbing before taps. You cannot have a functioning kitchen by installing beautiful taps on pipes that are not connected to anything. A lot of digitalization projects essentially do this. They invest in the visible, customer-facing elements before the underlying data and process infrastructure is in place to support them.

Forrester’s work on intelligent growth models touches on this sequencing challenge. The companies that scale digital capability most effectively are those that build foundational data and analytics capacity first, then layer commercial applications on top of it. The order matters enormously.

Where Marketing Leadership Fits in a Digitalization Strategy

Marketing leaders often find themselves in an awkward position in digitalization conversations. They are expected to be advocates for digital capability, but they are rarely given the structural authority to drive the decisions that matter most: data governance, technology stack, process redesign across functions.

The CMOs and marketing directors I have seen handle this well do a few things consistently. They translate commercial outcomes into technology requirements, rather than the other way around. They build relationships with finance and operations early, because digitalization is never a marketing-only project. And they are honest about what they do not know, particularly on the technology side, while being clear about what they do know, which is the customer and the commercial model.

There is also a specific role for marketing in ensuring that digitalization investments are evaluated against customer outcomes, not just operational metrics. A new CRM that makes the sales team’s reporting easier but does not improve how customers are served is a partial success at best. Marketing leadership should be the voice that keeps customer experience at the centre of the evaluation criteria.

The growth hacking literature, well-covered by sources like Crazy Egg’s breakdown of growth hacking frameworks, is useful context here. The discipline of connecting every digital initiative to a measurable growth outcome is something marketing can bring to the broader digitalization conversation, and it is a contribution that tends to be welcomed by boards who are nervous about ROI.

The Organisational Reality of Digital Transformation

I want to be direct about something that tends to get softened in transformation consulting decks. Digitalization creates winners and losers inside an organisation. It changes who has power, whose expertise is valued, and whose workflows get disrupted. Ignoring this reality does not make it go away. It just means the resistance shows up later, in the form of low adoption, workarounds, and passive non-compliance.

Early in my career, I was handed a whiteboard pen at a Guinness brainstorm when the agency founder had to leave for a meeting. Everyone in the room was senior to me. The internal reaction was visible: this was going to be uncomfortable. But the discomfort was the point. Real creative and strategic work requires people to operate outside their established hierarchies and comfort zones. Digitalization is the same. It requires people to let go of how things have always been done, and that is genuinely hard for most organisations.

The companies that handle this well invest in change management with the same seriousness they invest in technology. They communicate clearly about what is changing and why. They involve the people closest to existing processes in the redesign work, because those people have knowledge that no consultant or technology vendor has. And they create space for honest feedback about what is not working, rather than treating adoption metrics as a proxy for genuine engagement.

Vidyard’s research on pipeline and revenue potential for go-to-market teams highlights a specific version of this challenge: digital tools for sales and marketing teams only generate commercial return when the teams using them understand how to integrate them into their existing workflows. The technology is not the constraint. The workflow change is.

A Framework for Evaluating Digitalization Priorities

If you are trying to prioritise where to focus a digitalization strategy, a simple two-axis framework is more useful than most of the elaborate maturity models that consultants sell. The two axes are commercial impact and implementation readiness.

Commercial impact is a function of how directly the initiative connects to revenue, customer retention, or cost reduction. Implementation readiness is a function of whether the organisation has the data, the processes, and the people capability to execute the initiative well. Initiatives that score high on both axes are where you start. Initiatives that score high on commercial impact but low on implementation readiness are where you invest in building capability before you invest in technology.

The initiatives that score low on commercial impact but are easy to implement are the ones that fill up digitalization roadmaps without delivering meaningful results. They are the digital equivalent of repainting the office instead of fixing the roof. They generate activity and visible progress without addressing the underlying commercial opportunity.

Forrester’s analysis of go-to-market strategy challenges in complex industries illustrates how this plays out in practice. The organisations that struggle most with digitalization are those that have not connected their digital investments to a clear commercial model. The technology exists. The strategy does not.

This is also where the broader strategic context matters. Digitalization does not exist in isolation from your go-to-market model, your pricing strategy, or your customer segmentation. The growth strategy resources on The Marketing Juice cover how these elements connect, and why treating digitalization as a standalone initiative is one of the most common and costly mistakes companies make.

What Good Looks Like After Three Years

Three years is a reasonable horizon for evaluating whether a digitalization strategy has worked. It is long enough to see real commercial outcomes, and short enough that the original strategic intent should still be traceable.

The markers of a successful digitalization strategy at the three-year point are fairly consistent. Customer acquisition costs are lower or more predictable. Customer lifetime value has improved because the experience is better and retention is higher. The organisation has internal capability, not just vendor dependency. And the data infrastructure is generating insights that inform commercial decisions, rather than sitting in dashboards that nobody reads.

The markers of a failed digitalization strategy are also consistent. High technology spend with unclear commercial attribution. Low adoption of the tools that were supposed to change how people work. A data estate that is technically richer but practically no more useful than it was before. And a growing sense inside the organisation that “digital transformation” is something that happens to other companies.

The difference between these two outcomes is almost never the technology. It is the clarity of commercial intent at the start, the quality of the sequencing decisions in the middle, and the discipline of the measurement framework throughout. Those are strategy and leadership questions. They are the ones worth spending time on before the vendor conversations begin.

About the Author

Keith Lacy is a marketing strategist and former agency CEO with 20+ years of experience across agency leadership, performance marketing, and commercial strategy. He writes The Marketing Juice to cut through the noise and share what works.

Frequently Asked Questions