9 Digital Transformation Challenges (and How Modern Commerce Solves Them)

An outdated platform or an aging tech stack can quietly drain revenue for today’s brands. Not only does it slow tech teams down, but it also erodes revenue, customer trust, and operational efficiency. When technical debt starts showing up as delayed launches, rising maintenance costs, or frustrated customers, it’s a clear signal that the underlying technology is holding the business back. And costs go far beyond what you spend maintaining legacy systems: there are also the opportunities you miss, including new storefront experiences and new revenue streams.

Digital transformation has also become significantly more complex, especially for large and established organizations. Gartner reports that 94% of CIOs expect major changes to their digital plans and outcomes within the next 24 months. Yet only 48% of digital initiatives meet or exceed business targets. 

That gap is the paradox leaders face today. Everyone is “transforming,” but too many programs stall in planning cycles or get trapped by platforms that make every improvement slower and more expensive.

When transformation is done well, the upside is meaningful. Moving away from a rigid, legacy tech stack to a modern and flexible platform reshapes how teams operate and how customers experience your brand. Organizations ship faster. Innovation cycles shrink from months to weeks. Personalization becomes scalable instead of expensive. Customers stay loyal rather than defecting to competitors with more modern buying experiences. But digital transformation success isn’t only about choosing the right tools. It also comes down to execution: staying on time and on budget.

To help leaders navigate this reality, this article breaks down the nine most common digital transformation challenges businesses face today. It also outlines how to overcome them through smart platform choices, clear strategy, and disciplined execution.

Understanding digital transformation for modern commerce

Fast, personalized buying experiences, streamlined operations, and unified systems are now table stakes for ecommerce success. For organizations running on legacy platforms or fragmented tech stacks, achieving these outcomes requires digital transformation.

In a commerce context, digital transformation means modernizing operations and customer experiences through technology. This typically includes upgrading or replacing your ecommerce platform, integrating systems more effectively, and working with new solutions that expand what your teams can build, launch, and scale.

Digital transformation vs. digitization vs. digital adoption

When discussing digital transformation, it’s easy to blur related terms that actually describe very different activities. In ecommerce, digitization, digital transformation, and digital adoption each play a distinct role in modernizing a business. 

Understanding how they differ helps teams set realistic goals, sequence initiatives correctly, and measure success more effectively. It also helps explain why many transformation efforts stall: organizations often stop at digitization, or mistake adoption for transformation.

Many digital transformation initiatives begin with digitization. Converting manual or paper-based processes into digital data creates the foundation needed for deeper transformation. Once new platforms and systems are in place, digital adoption becomes critical. Training, enablement, and change management ensure the technology delivers real business value rather than an underused investment.

But without moving beyond digitization and sustained adoption, organizations can’t achieve the full impact of transformation.

Why digital transformation matters for commerce brands in 2026

Today’s brands face sky-high expectations from online buyers. In 2023, Forrester reported that 71% of B2B buyers were millennials or Gen Z, and that share continues to grow. These buyers expect B2B purchasing to feel just as intuitive, fast, and self-service as the direct-to-consumer (DTC) experiences they have every day. In this environment, standing still is not an option.

In ecommerce, digital transformation is often reflected in practical changes to how teams sell, fulfill, and support customers. This can include turning manual, rep-led B2B ordering into a self-service customer portal. It can also mean addressing the limits of an aging tech stack and investing in platforms and partners that unlock new capabilities across channels and customer touchpoints.

Businesses that delay modernization often find themselves constrained by slow releases, disconnected systems, and rising technical overhead that directly impact buying experiences and operational efficiency. 

When done well, digital transformation goes beyond incremental improvements like faster page loads or a new chatbot. It powers operational and strategic change by unifying systems and changing how innovation is done. Teams move faster. Experiences become more personalized and consistent across channels. Costs tied to maintaining legacy systems shrink. Most importantly, the business becomes easier to evolve, helping protect revenue, strengthen loyalty, and support long-term growth in an increasingly competitive commerce environment.

As these expectations reset the baseline for digital buying, digital transformation has shifted from a competitive advantage to a requirement for staying relevant.

The market shift: From optional to existential

Delivering the right buying experience and adapting as expectations change are now foundational to business success. Sixty percent of B2B buyers say their supplier’s ecommerce experience plays a critical role in the relationship. Nearly two-thirds have switched suppliers simply for a better digital experience. Friction is no longer tolerated, and legacy platforms that can’t deliver put revenue at risk.

Strategic commerce requires the right technology

Meeting these expectations depends on the technology powering your commerce operations. Speed, flexibility, and reliability are now competitive requirements. The wrong platform can limit growth and reduce conversion.

Luxury home décor brand Lulu and Georgia encountered this with their previous platform. Their ecommerce site suffered frequent crashes during everyday transactions, just as the business was ready to scale. Each performance issue directly translated into lost revenue.

“The growth of the company was at risk, and hence we wanted to move to a partner where scale or performance were not an issue,” said Anis Tayebali, vice president of engineering at Lulu and Georgia.

Despite managing a catalog of more than 40,000 SKUs, the team was able to migrate to Shopify faster than expected. They launched with an MVP, then layered in essential integrations through Shopify’s app ecosystem. Over time, they added capabilities their previous platform could not support, creating a foundation built for innovation and growth.

“I’d say the number-one improvement is we can scale the site. We don’t have to worry about a large-scale event taking down the site or checkout not working. We can now focus on our offerings, including providing other ways of purchasing or adding new apps that could provide customers with better functionality. We can take on more sessions, and we’re seeing the direct impact of this on our revenue. When we experience massive surges in demand, we can now take full advantage of that,” said Anis.

Thousands of brands have followed a similar path. Since its inception, Shopify has powered more than $1.1 trillion in global market value. And in the past year, Shopify stores have served over 875 million unique online shoppers. For commerce brands preparing for the realities of 2026, digital transformation becomes a strategic lever for growth, competition, and scale.

Nine critical digital transformation challenges 

Digital transformation initiatives often start with a strong vision and high hopes, but get mired in complexities and stall during execution. What looks promising on paper can turn into slow implementations, underused tools, and outcomes that fall far short of expectations. 

In commerce, success often comes down to planning and execution. Project leaders should anticipate common challenges early, align teams around clear outcomes, and choose technology that drives agility instead of adding complexity and cost.

Below are nine challenges that commonly derail transformation efforts, and what business leaders can do about them.

Challenge #1: The strategy-execution gap

Many brands undertake ambitious transformation strategies. Problems arise when those visions fail to translate into real-world execution. This disconnect is known as the “strategy–execution gap.” It reflects the difference between what leaders aim to achieve and what teams and technology are actually able to deliver.

Why transformation initiatives stall 

Filtrous offers a clear example of how this gap emerges in practice. Operating in a traditionally outdated laboratory supply industry, Filtrous set out to create a modern wholesale experience with faster checkout, streamlined fulfillment, and a frictionless buying journey. They selected BigCommerce, expecting a partner that could support rapid development and long-term scalability.

Instead, progress stagnated. The platform’s lack of out-of-the-box features meant they had to rely on developers to build the B2B experience. After a full year, the modern buying experience they wanted still wasn’t ready. Promised B2B capabilities lagged. Innovation was slow. Even minor site changes caused instability, making iteration risky and time-consuming.

"We did a full year of custom development for our site, but walked away unhappy with the way the site looked and performed. BigCommerce lacked the flexibility for us to fully control our site, and managing the customer experience was time-consuming,” said Yin Fu, director of ecommerce at Filtrous. 

This pattern is common in ecommerce transformations. Leaders set bold goals, platforms overpromise, and internal teams lack the time or resources to bridge the gap. The result is lost momentum and sunk costs. When that happens, execution slows; timelines slip, costs rise, and teams spend more time managing complexity than delivering value.

How to bridge the gap

After losing a year to the wrong platform, Filtrous reassessed their technology strategy and migrated to Shopify, a platform with a 20% faster implementation rate than other ecommerce solutions. In just 63 days, Filtrous launched a fully featured B2B buying experience. The platform enabled automation across purchasing workflows and delivered a significantly improved customer experience. Organic conversion rates increased by 27%.

Closing the strategy–execution gap starts with clear goals and a realistic roadmap from current to future state. Platform selection should follow strategy, not lead it. The right technology partner makes execution easier, faster, and more predictable. Choosing too early, or choosing based on promises rather than proven capability, often leads to costly delays and missed outcomes.

Challenge #2: Change resistance and cultural inertia

Technical challenges are not the only barrier to successful digital transformation. People are an important, yet often overlooked factor that can hamper success. Employees prefer familiar workflows. Managers underestimate the time required for training and enablement. And when progress is slow, fatigue sets in, causing even the strongest initiatives to lose momentum.

In ecommerce, even customers can resist change, especially in B2B environments where rep-led ordering has been the norm for years. Successful digital transformation requires planning for the people alongside the technology.

Why teams resist digital change 

Resistance to new tools and processes is common across businesses of all sizes. Once teams and customers are comfortable with a process, change can feel risky or unnecessary. Some employees worry about their ability to learn new systems or fear that automation could reduce their role. Others simply lack the time or support needed to adopt new workflows with confidence.

Customer reticence can also hinder transformation. In many B2B industries, buyers are accustomed to placing orders through familiar, manual processes. Even when self-service tools are faster and more efficient, adoption can be slow without clear guidance, onboarding, and reassurance. When early value isn’t visible, transformation is perceived as a disruption rather than an improvement.

Overcoming change-management challenges

The most effective digital transformation initiatives treat change management as a core workstream, not a side task. Executive and managerial buy-in is essential. Leaders must actively reinforce the purpose of the transformation and model adoption themselves.

Enablement matters just as much as implementation. Once new systems are live, you must invest in training for employees and structured onboarding for customers. Clear documentation, guided walkthroughs, and responsive support help build confidence early.

Finally, you should communicate the benefits in practical terms. Demonstrate to customers how self-service simplifies reordering and account management. Show internal teams how automation reduces manual work and improves customer support. When people understand how change makes their work easier or more effective, adoption becomes a shared goal rather than a forced transition.

Challenge #3: Legacy systems and technical debt

Many ecommerce transformations today are not about moving from paper to digital. They are about escaping a legacy “franken-stack” of outdated platforms, custom-built tools, and brittle integrations. Over time, these systems slow innovation, increase risk, and make it harder to meet modern buyer expectations.

Understanding the hidden costs of custom solutions

Custom-built and heavily customized solutions often start with good intentions. They appear cost-effective early on and give teams control over specialized requirements. For a while, in-house teams can manage them without issue.

As the business grows, however, complexity compounds. New integrations are required. Features must be rebuilt and maintained. Performance degrades under increased traffic. Even small updates take weeks instead of days. Maintenance costs rise, outages become more frequent, and the cycle of technical debt begins to shape business decisions rather than support them.

Eventually, the impact becomes visible everywhere. Customers encounter friction. Teams spend more time maintaining systems than improving experiences. 

Revenue suffers as innovation slows. And because costs are spread across maintenance and development, it can be hard to see the full total cost of ownership (TCO) until it becomes a constraint.

Allied Medical experienced this firsthand. As the business scaled, their customized open-source content management system (CMS) could no longer support growing B2B needs. Search was fragile, and a minor typing error could lead to dead ends instead of conversions. Online ordering lacked invoice history and efficient reordering. Internally, the team relied on manual workarounds to keep operations running.

“We had to manually add all B2B accounts and contacts, which caused errors and created inefficiencies. Clients were often forgetting passwords or shared logins which created frustration and additional work for our customer care team,” said Tania Barthorpe, marketing manager for Allied Medical.

Modern platform alternatives

After migrating to Shopify, Allied Medical was able to modernize their B2B experience and streamline operations. Inventory was unified across three warehouses, improving fulfillment speed and accuracy. Improved search functionality helped customers find specialized equipment more easily, reducing friction across the buying journey.

The internal team also gained much-needed agility. They could launch new features without relying on developers, significantly lowering technical overhead. Streamlined operations reduced time spent on back-end tasks by 40%, drove a 14% increase in transaction volume across channels, and lifted online revenue by 4.7%.

“The big thing for us is that the new platform is built for the future. Thanks to Shopify, we’re well positioned for long-term scalability without having to expand resources. We’ve moved from a platform that held us back to one that empowers us to scale, automate, and provide a better experience for our customers,” said Katie Noble, managing director for Allied Medical.

Modern commerce platforms enable faster, lower-risk digital transformation. With Shopify, brands can adopt a composable architecture, adding functionality through a large ecosystem of preintegrated apps instead of custom builds. That reduces—or more often, fully eliminates—the amount of custom code teams need to maintain. Businesses move from long development cycles to faster, lower-risk iterations.

For organizations with more complex requirements, Shopify also supports headless implementations through robust application programming interfaces (APIs), allowing teams to unify back-end operations while customizing front-end experiences.

Across both approaches, Shopify removes the burden of hosting, maintenance, and security through a global, cloud-based infrastructure. The result is lower technical risk, faster iteration, and a lower total cost of ownership, allowing ecommerce teams to focus on growth rather than maintenance. On average, modern platforms can deliver 33% better total cost of ownership and 23% better platform costs, freeing budget for innovation instead of upkeep.

Challenge #4: Skills gaps and talent shortage

In ecommerce transformations, the challenge is almost never a lack of ambition. Teams with lofty goals hit a wall when they have to source the technical capacity to bring them to life. Hiring and retaining experienced developers is expensive, competitive, and time-consuming. Outsourcing to agencies can accelerate delivery, but costs often scale faster than budgets. When transformation depends heavily on custom development, progress slows and flexibility disappears.

How technical resource costs climb

Brands running legacy platforms or highly customized stacks often pay a premium just to maintain existing functionality. What begins as a cost-saving or flexible solution gradually turns into a maintenance burden. Teams spend more time managing integrations, patching custom code, and addressing performance issues than improving the buying experience. Costs go up simply to keep the lights on, and more investment is needed for every new feature and capability.

Some ecommerce platforms promise flexibility but require constant developer involvement. As a result, businesses end up paying both platform fees and ongoing development costs. The outcome is slower execution, steadily rising overhead, and limited room to experiment.

Freeing up technical talent to drive innovation

When you choose a platform and provider like Shopify for digital transformation, you get a wide range of features and functionality right out of the box. You can partner with an experienced agency to streamline migration and site creation, but then manage a vast majority of updates like adding new products and discounts with in-house teams.

Shopify also lets you add new features and functionality quickly with thousands of preintegrated apps, all maintained by the app provider, not your in-house team. Because the platform is intuitive and easy to use, your teams can get up to speed quickly, and even experiment and innovate with new features and functionality, all without the need for pricey developers. 

When technical teams aren’t spending time making sure basic functionality is working, they can focus on innovating to drive new business and deliver better buying experiences. In practice, simpler platforms help teams move faster by reducing bottlenecks and maintenance work.

Challenge #5: Disparate systems and integration complexity

Digital transformation can unintentionally create new complexity when systems are modernized in isolation. As inventory, marketing, order management, and fulfillment each evolve, brands can end up with disconnected tools, data silos, and fragile integrations.

When systems aren’t connected

Disconnected systems create daily friction for both teams and customers. Orders placed online may need to be manually reentered into fulfillment systems. Customer data from ecommerce transactions may never reach marketing or customer relationship management (CRM) tools. Each manual step increases operational overhead and introduces opportunities for error.

These gaps also limit visibility. Without real-time data syncing across systems, teams lose insight into customer behavior, inventory availability, and order status. Personalization and data-driven decision making become harder to scale. Instead of acting on timely, consistent information, teams spend time comparing data across tools.

Some organizations attempt to solve this by building custom integrations. While this can reduce manual work in the short term, it often introduces new risks. Custom connections are brittle and require ongoing maintenance. Each platform update can trigger unexpected breakages, pulling technical teams back into reactive work.

The benefits of unified, integrated systems

A successful ecommerce transformation prioritizes unification. With a platform like Shopify, businesses can centralize commerce operations around a single back end while integrating seamlessly with core systems such as CRMs and enterprise resource planning platforms (ERPs). 

Data syncs in real time across the buying journey, reducing manual effort and improving accuracy. For teams, the goal is simple: fewer handoffs, fewer errors, and a clearer view of what customers are doing, as well as what the business needs to do next.

With a unified source of truth, teams can automate operations and move faster. Self-service B2B portals support complex ordering without heavy sales involvement. Preintegrated apps extend functionality with personalization, loyalty, tax, and pricing logic. Additional systems can be connected without introducing long implementation cycles or excessive technical cost.

And because Shopify powers 12% of US ecommerce, brands benefit from an ecosystem of integrations and partners. The burden of building and maintaining one-off connections is reduced, or even removed entirely.

This is where digital transformation delivers long-term value. A unified commerce foundation reduces complexity today and creates the flexibility to adapt as business needs change.

Challenge #6: Budget constraints and unpredictable costs

Across industries, digital transformation begins as an investment. Leaders expect new tools and technology to easily solve complex processes and operational challenges. In reality, initial estimates almost never account for everything, and costs multiply quickly. And the costs are significant: global spending on digital transformation reached $2.58 trillion in 2025 and is projected to grow to $3.88 trillion by 2028.

For commerce brands specifically, the risk is not just the size of the investment, but how unpredictable that investment can become.

Why digital transformation blows budgets 

Technology implementations rarely go exactly as planned. Capabilities are overpromised. Adoption takes longer than expected. Processes turn out to be more complex once systems are in use. Hidden costs emerge as edge cases, integrations, and exceptions surface late in the project.

Scope creep is almost inevitable. Unplanned systems need to be connected. Additional workflows get added. “Nice-to-have” features become requirements. What started as a targeted improvement can stretch into a monthslong initiative that exceeds budget, delays value, or stalls entirely. When that happens, it’s harder to maintain confidence in the business case.

Predictable investment strategies

But digital transformation does not have to be this financially volatile. Predictability starts with planning for total cost of ownership, not just licensing or up-front fees. This includes implementation, ongoing development, maintenance, and the internal resources required to operate the platform long-term.

Platform choice is the biggest factor. Providers with proven implementation models and mature ecosystems reduce financial risk. For example, an independent consulting firm shows that Shopify implementations had 23% lower costs and were three times more likely to stay on budget. 

Phased rollouts also help control costs and accelerate returns. Many Shopify customers launch with a minimum viable product, then expand functionality incrementally using preintegrated apps. This approach shortens time to value, limits up-front spend, and allows teams and customers to adapt gradually. Return on investment (ROI) increases over time as new capabilities are layered in and processes continue to improve.

Challenge #7: Security and compliance concerns

Digital transformation almost always raises questions about security and risk. Modern commerce platforms rely on cloud infrastructure, real-time integrations, and the exchange of sensitive customer and financial data. But without the right safeguards in place, transformation efforts can expose new vulnerabilities rather than eliminate old ones.

Risk management in digital transformation 

Many legacy systems were not designed for today’s threat landscape. In that sense, digital transformation can actually improve security—but only if vendors, platforms, and integrations are carefully evaluated end to end. When security is built in from the start, it can help teams move faster.

Compliance requirements must be addressed early. Regulations such as GDPR and PCI DSS are not optional, especially if you have global customers. A transformation that overlooks these requirements can quickly create risk, including breaches, fines, and loss of customer trust. Security cannot be bolted on after launch. It must be built into the transformation from the start.

Building secure digital foundations

The strongest transformations begin with disciplined vetting of vendors and a holistic view of security across every connected system. At a minimum, commerce platforms should offer:

• Built-in, enterprise-grade security
• Compliance certifications already in place
• Automated updates and patching
• Managed, global cloud infrastructure

Platforms like Shopify are designed to handle these requirements by default, reducing the burden on internal teams. With infrastructure, security updates, and compliance managed at the platform level, you can lower risk while freeing technical resources to focus on innovation and customer experience rather than maintenance.

Challenge #8: Measuring ROI and proving value

Getting a digital transformation live is hard enough. Proving its value often comes later, or not at all. Without a clear way to measure impact, leaders struggle to validate platform decisions, justify further investment, or understand where transformation is actually delivering results.

The attribution challenge 

Digital transformation affects multiple parts of the business at once. A new ecommerce experience can save sales reps time, reduce operational errors, improve conversion rates, and increase customer loyalty. Each of these outcomes shows up in different metrics, on different timelines.

Some gains are immediate, such as higher conversion rates or increased order volume. Others take longer to surface, including reduced time spent on support, improved retention, or efficiency gains across sales and IT teams. This makes attribution difficult unless measurement is planned in advance. And when delivery is slow, it can take longer to see results, making it harder to maintain stakeholder confidence.

Metrics that matter

Measuring ROI starts before implementation. Establish baseline performance data before making changes so results can be compared accurately. Define success metrics early, and ensure they reflect both revenue impact and operational efficiency. For ecommerce transformations, good KPIs to track include:

• Time saved by sales, support, and IT teams
• Conversion rate, cart abandonment, and traffic growth
• Changes in average order value (AOV)
• Reductions in order errors and support requests
• Improvements in repeat purchase and retention rates

Revenue lift is especially important. Cost-savings matter, but growth compounds over time. For example, brands that migrate from legacy platforms to Shopify see an average of 15% more revenue, as well as 15% higher checkout conversion. Tracking these outcomes helps teams understand not just whether transformation worked, but where continued investment will deliver the greatest return.

Challenge #9: Keeping up with rapid technology change

To stay competitive today, brands must continuously evolve the buying experience. Today’s B2B buyers engage across an average of 10 channels throughout their purchasing journey, and 60% say their supplier’s ecommerce experience is very important to the overall relationship. A core goal of any digital transformation should be building the agility to keep up with this pace of change.

Chasing innovation with legacy solutions

What feels innovative today quickly becomes baseline tomorrow. When major retailers introduce new capabilities, buyers begin to expect similar experiences everywhere. Brands that cannot roll out improvements quickly risk frustration, disengagement, and lost loyalty.

Legacy platforms struggle to keep up with this reality. Maintaining custom systems consumes time and budget that could otherwise be spent on innovation. Even highly capable teams often find themselves focused on stability, security, and upkeep rather than improving the customer experience. 

Over time, this can make businesses more fragile: each new change introduces more risk and more hesitation to ship.

Future-proofing your commerce stack

Innovation is expensive. One of the most effective ways to manage that cost is to outsource it to the right platform and provider. 

In 2024 alone, Shopify invested $1.4 billion in research and development to continuously improve its commerce capabilities. That investment is shared across our customer base, giving brands access to new features without absorbing the full cost themselves. Instead of rebuilding capabilities in-house, teams can take advantage of improvements as the platform evolves.

Beyond the core platform, Shopify’s ecosystem of thousands of apps allows businesses to extend functionality as needs evolve. This flexibility supports experimentation. Teams can launch MVP experiences, test new features, measure adoption, and iterate quickly without long development cycles.

Future-proofing digital transformation is not about predicting every requirement years in advance. It is about choosing a foundation that allows the business to adapt, experiment, and evolve as buyer expectations continue to change.

Solve your digital transformation challenges with a modern commerce platform

Digital transformation is no longer optional for commerce brands. But execution quality determines whether it becomes a growth lever or a sunk cost. Across every challenge explored in this guide, including speed, cost, skills, integration, security, and ROI, one pattern is clear: outcomes depend less on intent and more on how effectively teams can execute on the right technology foundation.

Modern commerce platforms built for transformation create sustained value over time. Faster migrations reduce risk. Lower total cost of ownership frees budget. Productivity gains compound as teams spend less time maintaining systems and more time improving experiences. Speed becomes a strategic advantage, not just an operational improvement.

The opposite is also true. The cost of inaction compounds daily. Every day spent on legacy systems is a day competitors move faster and capture more market share—and potentially your own customers. Every delay makes future change harder and more expensive.

Platforms like Shopify are designed to support continuous improvement and innovation. Its API-first architecture, seamless integrations, and extensive app ecosystem enable flexibility without unnecessary complexity. The result is faster launches, greater agility, and sustained momentum after go-live, as well as a scalable foundation for future projects.

When ecommerce transformation succeeds, technical debt shrinks, team productivity increases, and innovation becomes continuous. The right foundation not only helps you modernize, it determines how quickly and confidently you can adapt to whatever comes next.

To learn more about how Shopify accelerates digital transformation, read our time-to-value guide, or schedule a demo with an ecommerce expert today.