From Legacy Tech to Cloud-Native: Modernizing Retail Infrastructure

Retail organizations today face unprecedented pressures, from rapidly changing customer expectations to surging data volumes and omnichannel complexity. Many still rely on legacy systems that have faithfully powered their operations for decades. While these systems are battle-tested, they increasingly inhibit agility and scalability, limiting retailers’ ability to respond quickly to market changes and customer needs across online and physical stores.

Cloud-native modernization directly impacts key business drivers: it accelerates time-to-market for customer experiences, minimizes service outages in high-volume events like Black Friday, and enables seamless omnichannel retailing.

Why Modernize?

Legacy systems in retail are powerful, but may become bottlenecks that restrict growth and innovation. They pose several risks, including:

• Inability to scale quickly during peak seasons, such as holiday sales spikes
• Incurring higher operational costs due to aging hardware and maintenance requirements
• Difficulty integrating new digital experiences to meet evolving customer expectations
• Potential for unpatchable security vulnerabilities in outdated architectures

Cloud-native architectures address these pain points by enabling retailers to innovate rapidly, secure sensitive data more effectively, and scale infrastructure dynamically according to demand, whether online, in-store, or both.

What’s at Stake: Retailers that delay modernization risk higher operational costs, security vulnerabilities, and the inability to meet customer expectations for fast, reliable service.

What Does “Cloud Native” Really Mean?

According to the Cloud Native Computing Foundation (CNCF):

Cloud native technologies empower organizations to build and run scalable applications in dynamic environments such as public, private, and hybrid clouds. Containers, service meshes, microservices, immutable infrastructure, and declarative APIs exemplify this approach. These techniques enable loosely coupled systems that are resilient, manageable, and observable. Combined with robust automation, they allow engineers to make high-impact changes frequently and predictably with minimal toil.

Cloud native is not merely lifting legacy apps to the cloud, but fundamentally building systems to take full advantage of cloud scalability, automation, and resilience.

Key cloud-native characteristics of cloud-native architectures include:

• Loosely coupled systems that interoperate securely without tight dependencies
• Containers and microservices to enable modular development and faster innovation
• Service meshes (software layers that help manage secure communication and monitoring between parts of complex applications), Application Programming Interfaces (APIs), and declarative infrastructure, which can improve observability and enable more automation
• Serverless capabilities to run code without managing servers or scaling manually

Legacy vs. Cloud-Native Infrastructure from a Retail Perspective

Security & Compliance Considerations in Retail

Retailers operate under stringent regulatory requirements designed to protect customer data and ensure secure transactions. These regulations include the Payment Card Industry Data Security Standard (PCI DSS), the General Data Protection Regulation (GDPR) in the European Union, and the California Consumer Privacy Act (CCPA) in the United States, among others. Each of these regulations mandates rigorous controls on how sensitive information, such as payment details and personal customer data, is processed, stored, and transmitted.

Cloud-native modernization introduces new complexities for compliance because applications and data are distributed across dynamic, multi-cloud environments that use modern technologies, such as containers, microservices, and Kubernetes. To meet compliance requirements effectively, retailers must:

• Encrypt sensitive data at rest and in transit, ensuring protection against unauthorized access during storage and transmission.
• Implement continuous monitoring and auditing mechanisms to track access, detect anomalies, and maintain logs for forensic analysis (in case of a material cyber incident) and regulatory reporting.
• Use Policy-as-Code frameworks, such as Kyverno (an open-source Kubernetes Policy-as-Code tool), to enforce security and compliance policies automatically across Kubernetes clusters, reducing manual errors and guaranteeing consistent governance.
• Adopt Infrastructure-as-Code (IaC) tooling (such as Terraform, an open-source IaC tool that automates cloud resource provisioning) to standardize infrastructure deployments, enabling repeatability and verifiable configurations that meet compliance baselines.
• Coordinate regularly with cloud service providers’ compliance certifications and audit reports to align internal controls with their shared security responsibilities.

Failure to embed these controls thoroughly during cloud-native transformation projects may expose retailers to regulatory fines, operational disruption, and reputational harm. The best approach is to build security and compliance in from the start as a continuous, automated element of the modernization journey.

Steps to a Cloud-Native Transformation

1. Start your transformation with assessing and planning.

Use the Cloud Native Maturity Model (CNMM), which is a CNCF model designed to help assess your current readiness and guide your transformation planning. This will help you chart progress along your modernization journey. Key recommendations include:

• Pilot projects with low-risk applications to test tooling and processes.
• Invest in continuous team training on cloud native concepts, containers, and Kubernetes.

2. Choose a migration path based on your CNMM assessment outcomes.

Typically, that will be one of the following options:

• Lift and Shift (Rehost): Move your application as-is to the cloud.
• Re-platform: Move the application with minor changes to use cloud services (for example, using a managed database service offered by a cloud provider).
• Refactor: Rework the application code to use cloud-native features.
• Rebuild: Start from scratch, developing a new, cloud-native application.

3. Mitigate risks

• Automate deployments via continuous integration and continuous delivery (CI/CD) and IaC to reduce manual errors.
• Implement comprehensive monitoring and logging (known as observability) from day one.
• Prepare rollback plans to recover quickly from failures.

4. Address security and compliance questions throughout

• Embed policy enforcement and monitoring capabilities.

Real-World Case Studies

Framebridge: Scaling to Meet Demand

As an online bespoke framing service, Framebridge needed to scale for both digital and brick-and-mortar growth. Their challenges included:

• Complex upgrades while using kOps caused downtime and off-hours firefighting
• Network issues hindered innovation and required excessive maintenance time
• Engineering resources were consumed by infrastructure management, not product growth

With expert guidance from Fairwinds, Framebridge now has:

• Migrated from kOps to Amazon EKS using Terraform for consistent infrastructure management
• Established a process for smoother, documented upgrades within specified work hours (9-5 ET)
• Streamlined CI/CD pipelines, enhancing deployment velocity and reliability.

Through improved infrastructure stability and scalability, the engineering teams can fully concentrate on product development and scaling growth, leading to both increased morale and improved operational efficiency.

Fast-Moving Food Company: Securing and Standardizing Kubernetes

This national food service company faced several challenges, including:

• No dedicated platform team
• Lack of in-house Kubernetes experience
• Tight timelines for cloud adoption without disrupting ongoing operations

Fairwinds Managed Kubernetes-as-a-Service stepped in to:

• Rapidly stand up cloud-native infrastructure, enabling a gradual adoption
• Deploy automated policy enforcement using Kyverno without disrupting business
• Integrated Gloo Gateway (a Kubernetes-native API Gateway and ingress controller) as Kubernetes ingress controller, managing cutover to avoid downtime
• Continuous vulnerability scanning and remediation plans developed with client teams

The team achieved the highest levels of security and compliance. It also built internal expertise through hands-on collaboration with Fairwinds Site Reliability Engineers (SREs), which enabled a low-risk path to cloud-native adoption.

Future-Proof Your Retail IT

The open-source ecosystem evolves rapidly, with new projects, features, and security approaches emerging frequently. To keep pace and stay competitive, retail organizations must foster a culture of continuous learning, agility, and proactive skill development. To succeed in cloud-native modernization, your organization must:

• Approach transformation incrementally, starting small and learning fast
• Prioritize automation, observability, and security as foundational elements
• Invest in people and culture alongside technology
• Recognize that continuous evolution is essential to meet future retail challenges

Is your infrastructure flexible enough to handle the next holiday rush or high-profile sales event without disruption? Can your teams confidently deploy new features and security patches rapidly and safely?

Addressing these questions today will empower your retail business to compete, innovate, and meet the changing requirements of your customers tomorrow.