Digital Maturity in Retail: Where You Are Now vs. Where You Need to Be in 2026

As we close in on the end of the year, many retailers are reflecting on performance, setting budgets, and planning for the year ahead. Which makes now the right time to assess your digital maturity, especially when it comes to your point-of-sale (POS) ecosystem.

In this article, we’ll define what digital maturity means in a retail context, outline the five core areas to evaluate, and introduce two models you can use to benchmark your current state. We’ll also take a closer look at where leading retailers are heading by 2026, what trends they’re embracing, and how to move forward without falling into common traps.

What is Digital Maturity?

Digital maturity is how well your entire technology ecosystem supports your strategy and day-to-day operations. It goes beyond having a mobile app or an online store. It means your software, hardware, processes, and teams are working together to deliver a seamless, scalable experience for both your customers and your employees.

In a nutshell: is your technology working for you, or are you constantly working around it?

How to Assess Digital Maturity in Retail

Now that we’ve established a baseline of what digital maturity is, the next step is knowing how to measure it. When we work with retailers, here’s what we evaluate:

Customer Experience

Start from the customer’s point of view. Can a customer start a return online and finish it in-store? Are loyalty sign-ups simple? Do displays or kiosks make checkout clearer? Is the experience personalized and consistent across every channel? Or are customers feeling friction between channels?

Data & Insights

Is your data helping you make informed decisions, or is it siloed? Do teams rely on nightly printed reports, or are real-time insights available to them? Are you using data to forecast, personalize, and make proactive decisions?

Technological Infrastructure

What’s the current state of your hardware and software, and can it support what’s next? It’s critical to assess the age, condition, and capabilities of your core systems. How old are your POS terminals, printers, and mobile devices? Can customers use their phones for key actions like scanning or self-service? Are systems modular enough to evolve, or are you stuck with all-or-nothing upgrades?

Operational Agility

Consider how quickly your business can respond to change. How fast can you roll out updates or launch new features? Are development cycles long and rigid, or nimble and responsive? Can store associates solve problems on the spot, or do they have to escalate everything?

Platform Synchronicity

Examine how your systems are built to work together. Are they tightly or loosely coupled? At the end of the day, your systems need to play nice with each other.

Our Retail Digital Maturity Models

To make these six aspects easier to assess in the real world, we’ve combined them into our own digital maturity models. These models give retailers a practical way to benchmark where they are today and what it’ll take to reach the next level.

Retail Digital Maturity Model

This chart looks at maturity across five key dimensions: customer experience, data and insights, technology infrastructure, operations, and payments.

Hardware Maturity Model

Retailers often overlook hardware in digital transformation efforts, but aging, inflexible hardware can bottleneck even the smartest software.

What a Digitally Mature Retailer Will Look Like in 2026

Once you understand where you are, the next question is: where do you need to be?

By 2026, retailers will need more than mobile apps and online checkouts. Customers expect a fully connected, omnipresent shopping experience, one that works no matter where they are or how they engage. Whether browsing online, walking the aisles, or scrolling from the couch, they want a seamless journey.

Here’s what that looks like IRL:

Modern architecture: Flexible, API-driven platforms make it easier to integrate systems, add new capabilities, and keep everything in sync. This is what allows online and in-store to feel like one experience, not two.
Modular systems: Both hardware and software need to be easy to update, swap, and scale. Swappable hardware and decoupled software let you upgrade or troubleshoot without taking the whole operation offline. It keeps your systems resilient, adaptable, and consistent across every touchpoint.
Faster development cycles: Shorter release timelines mean you can respond to customer needs in real time, launching new features, fixing bugs, or testing experiences without waiting months. This ensures your omnichannel experience can evolve as quickly as shopper expectations do.

Additionally, leading retailers will be implementing these trends and technologies to support seamless, scalable operations:

Edge computing: Supports resiliency and reduces downtime
Remote device management: Allows centralized updates and troubleshooting without sending techs on-site
Computer vision: Powers asset protection, queue management, and item recognition at checkout
Electronic shelf labels: Enables real-time, dynamic pricing and reduces manual labor
AI Integration: Not just for buzzword appeal, but for real business cases that reduce costs, optimize workflows, and improve decision-making
Dark stores: Support BOPIS and delivery models with faster, localized fulfillment

How to Mature without Failing

Digital maturity is a process. And while the goal is to move fast, it’s just as important to move smart.

Many retailers run into the same pitfalls:

Getting locked into rigid platforms that can’t evolve
Spending heavily without a clear understanding of the return on investment
Adopting new technology based on trends instead of business needs
Allowing teams to operate in silos, with limited collaboration or data sharing
Overlooking the need for change management and internal alignment

Avoiding these missteps starts with getting clear on your goals. What problems are you solving? What capabilities do you want to unlock? Which teams need to be involved in the process?

From there, build a roadmap that is flexible and phased. You don’t have to do everything at once. Start with the most critical areas, validate impact early, and adjust as you go.

Conclusion

Digital maturity isn’t about chasing every trend. It’s about building a smarter, more flexible retail environment that supports your business goals and delights your customers. That kind of transformation doesn’t happen overnight, and it doesn’t have to happen alone.

At Kitestring, we’ve helped retailers of all sizes assess their current state, align on a clear strategy, and implement systems that actually work across POS, mobile, loyalty, payments, and more.

Whether you need help building a technology roadmap, modernizing legacy tech, or selecting and implementing a new core system, we’re here to support you as a strategic, end-to-end partner.

Digital Maturity in Retail: Where You Are Now vs. Where You Need to Be in 2026

As we close in on the end of the year, many retailers are reflecting on performance, setting budgets, and planning for the year ahead. Which makes now the right time to assess your digital maturity, especially when it comes to your point-of-sale (POS) ecosystem.

What is Digital Maturity?

In a nutshell: is your technology working for you, or are you constantly working around it?

How to Assess Digital Maturity in Retail

Now that we’ve established a baseline of what digital maturity is, the next step is knowing how to measure it. When we work with retailers, here’s what we evaluate:

Customer Experience

Start from the customer’s point of view. Can a customer start a return online and finish it in-store? Are loyalty sign-ups simple? Do displays or kiosks make checkout clearer? Is the experience personalized and consistent across every channel? Or are customers feeling friction between channels?

Data & Insights

Is your data helping you make informed decisions, or is it siloed? Do teams rely on nightly printed reports, or are real-time insights available to them? Are you using data to forecast, personalize, and make proactive decisions?

Technological Infrastructure

Operational Agility

Consider how quickly your business can respond to change. How fast can you roll out updates or launch new features? Are development cycles long and rigid, or nimble and responsive? Can store associates solve problems on the spot, or do they have to escalate everything?

Platform Synchronicity

Examine how your systems are built to work together. Are they tightly or loosely coupled? At the end of the day, your systems need to play nice with each other.

Our Retail Digital Maturity Models

To make these six aspects easier to assess in the real world, we’ve combined them into our own digital maturity models. These models give retailers a practical way to benchmark where they are today and what it’ll take to reach the next level.

Retail Digital Maturity Model

This chart looks at maturity across five key dimensions: customer experience, data and insights, technology infrastructure, operations, and payments.

Hardware Maturity Model

Retailers often overlook hardware in digital transformation efforts, but aging, inflexible hardware can bottleneck even the smartest software.

What a Digitally Mature Retailer Will Look Like in 2026

Once you understand where you are, the next question is: where do you need to be?

Here’s what that looks like IRL:

Modern architecture: Flexible, API-driven platforms make it easier to integrate systems, add new capabilities, and keep everything in sync. This is what allows online and in-store to feel like one experience, not two.

Modular systems: Both hardware and software need to be easy to update, swap, and scale. Swappable hardware and decoupled software let you upgrade or troubleshoot without taking the whole operation offline. It keeps your systems resilient, adaptable, and consistent across every touchpoint.

Faster development cycles: Shorter release timelines mean you can respond to customer needs in real time, launching new features, fixing bugs, or testing experiences without waiting months. This ensures your omnichannel experience can evolve as quickly as shopper expectations do.

Additionally, leading retailers will be implementing these trends and technologies to support seamless, scalable operations:

Edge computing: Supports resiliency and reduces downtime

Remote device management: Allows centralized updates and troubleshooting without sending techs on-site

Computer vision: Powers asset protection, queue management, and item recognition at checkout

Electronic shelf labels: Enables real-time, dynamic pricing and reduces manual labor

AI Integration: Not just for buzzword appeal, but for real business cases that reduce costs, optimize workflows, and improve decision-making

Dark stores: Support BOPIS and delivery models with faster, localized fulfillment

How to Mature without Failing

Digital maturity is a process. And while the goal is to move fast, it’s just as important to move smart.

Many retailers run into the same pitfalls:

Getting locked into rigid platforms that can’t evolve

Spending heavily without a clear understanding of the return on investment

Adopting new technology based on trends instead of business needs

Allowing teams to operate in silos, with limited collaboration or data sharing

Overlooking the need for change management and internal alignment

Avoiding these missteps starts with getting clear on your goals. What problems are you solving? What capabilities do you want to unlock? Which teams need to be involved in the process?

From there, build a roadmap that is flexible and phased. You don’t have to do everything at once. Start with the most critical areas, validate impact early, and adjust as you go.

Conclusion

Digital maturity isn’t about chasing every trend. It’s about building a smarter, more flexible retail environment that supports your business goals and delights your customers. That kind of transformation doesn’t happen overnight, and it doesn’t have to happen alone.

At Kitestring, we’ve helped retailers of all sizes assess their current state, align on a clear strategy, and implement systems that actually work across POS, mobile, loyalty, payments, and more.

Whether you need help building a technology roadmap, modernizing legacy tech, or selecting and implementing a new core system, we’re here to support you as a strategic, end-to-end partner.