Specialty Retailer Validates POS Strategy and Cuts POS Costs in Half

Introduction

A fast-growing specialty retailer was continuing to open new stores, but their point-of-sale (POS) system was nearing end of life. The system was not changing as quickly as the retailer needed, and according to internal projections, the company had roughly a two-year runway before the existing platform would begin hitting limitations that could make it unstable or inoperable.

The retailer’s IT organization already had a good idea of which next-generation POS system it wanted to pursue. It had evaluated vendors, had a target platform in mind, and had received a multi-million-dollar five-year quote from the preferred vendor. What it did not yet have was an outside perspective to validate that direction or a structured process that brought the broader business into the decision.

That alignment was especially important because the retailer was growing. Its existing system could not support future growth at the pace the business required, and it also lacked functionality the company wanted for areas such as eCommerce and true omni-commerce connections. The business had things it wanted to try and changes it wanted to make, but it simply couldn’t go fast enough on the old system.

Kitestring stepped in to complete a tailored selection study designed to validate the path forward, bring rigor and healthy competition into the conversation, and create alignment across IT, the business, and prospective vendors.

Problem Statement

Time was becoming a significant factor. A major POS replacement requires substantial planning, design, development, testing, and rollout effort, while the retailer had only about two years of expected runway remaining on its current platform.

The challenge also extended beyond future system stability. The retailer needed more flexibility from its store technology environment. The business wanted tighter integration between stores and digital commerce, greater ability to introduce new customer experiences, and a platform that could support continued growth without becoming a constraint.

The technology decision also needed broader participation from across the organization. IT had already developed a strong perspective on the market, but business stakeholders had not yet been fully involved in defining the capabilities and outcomes the future platform needed to support.

Finally, the retailer had a significant commercial decision in front of it. Its preferred vendor had submitted a multi-million-dollar proposal for software and implementation services. Rather than restart their evaluation, the retailer needed a disciplined way to test the work already completed and determine whether the preferred direction held up against the broader market.

Solution

Kitestring tailored its POS selection process to build on the retailer’s existing work rather than repeat it. The engagement began by bringing business and technology stakeholders together to establish the requirements for the next-generation platform.

Kitestring wasn’t just building a feature checklist.  Our team was identifying the capabilities the retailer would need for future growth and flexibility.  The goal was to have a system that could move with the business and enable them to tailor the checkout experience. Those requirements became the foundation for a structured evaluation of the leading POS platforms.

Kitestring also evaluated each solution within the context of the retailer’s broader technology environment. The decision was not based solely on which POS platform offered the largest number of features. Each option was assessed based on its ability to meet business needs, fit within the retailer’s technology ecosystem, support the implementation approach, and provide acceptable commercial terms.

Kitestring’s experience in the retail POS market and established relationships with major vendors also helped the retailer work through questions and issues efficiently during the evaluation. Most importantly, the process created genuine competition around a decision that had previously been moving toward a single vendor.

Methodology and Implementation

Kitestring began by engaging stakeholders across both the business and technology sides of the organization. Those discussions were used to establish and prioritize the functional and technical requirements for the next-generation platform, along with the capabilities needed to support future growth and changing business needs.

The requirements were then used to evaluate the available products and vendors through Kitestring’s Tell, Show, Prove framework:

• Tell: Vendors responded to detailed written requirements outlining the capabilities the retailer needed.
• Show: Vendors demonstrated how their platforms supported the retailer’s priority use cases and capabilities.
• Prove: Where additional validation was appropriate, capabilities could be tested in a lab environment to confirm that the technology performed as represented.

The evaluation also considered how each solution would operate within the retailer’s broader technology ecosystem, including integration requirements, implementation complexity, and commercial structure.

While Kitestring maintains a standard selection methodology, this engagement was intentionally tailored to the retailer’s situation. Rather than replace the work the organization had already completed, Kitestring added structure, outside expertise, broader stakeholder participation, and competitive pressure to the existing process.

Key Results

• Created competitive leverage by bringing multiple vendors into the evaluation rather than proceeding directly with the preferred vendor.
• Reduced proposed POS software and implementation costs by 50%, cutting a multi-million-dollar proposal in half.
• Validated the retailer’s preferred POS direction through a structured, competitive evaluation.
• Aligned business and IT stakeholders around the requirements and priorities for the next-generation platform.
• Established a clear path to execution, with requirements defined, vendor expectations documented, and the organization positioned to move into contracting and implementation.

The result was more than a vendor recommendation. The retailer had a validated technology strategy, organizational alignment, and a substantially better commercial position.

Conclusion

A successful selection study does not always result in choosing a different vendor. In some cases, the retailer has already done enough work to identify the likely direction.

The value of Kitestring’s selection study process is in validating that conclusion, bringing the broader business into the decision, understanding credible alternatives, and creating the leverage needed to negotiate effectively.

In this case, the retailer entered the engagement with a preferred POS platform, a multi-million-dollar proposal, and a limited window to replace its existing system. It left with a validated direction, broader organizational alignment, and a commercial proposal that had been reduced by approximately half.

Most importantly, the retailer was positioned to move from evaluating its future POS strategy to executing that strategy.