Sam Kliger

Founder & CEO KWI

Last Reviewed: September 19, 2026

Executive Summary

Sam Kliger has run the same company for forty-one years. He founded KWI in 1985 at nineteen after walking into a Benetton store, noticing how long the queues were, and spending several months writing code to shorten them. He quit school to deliver the result — a hosted, centrally managed point-of-sale system that KWI describes as the first SaaS-based managed services solution in retail, built roughly two decades before “software as a service” existed as a term. The company has stayed on that model ever since: cloud-delivered retail systems bundled with the managed services to run them, sold to fashion and specialty brands across thousands of locations. KWI has taken no outside investment across its entire history, reports an average customer tenure of fifteen years, and won Overall RetailTech Innovation of the Year at the 2026 RetailTech Breakthrough Awards for AI product image search.

Career Highlights

• Founded KWI in 1985 at nineteen, leaving school to deliver the Benetton system the company calls retail’s first SaaS-based managed services solution.
• Has led the company continuously for four decades, with $0 of outside investment.
• Reports an average customer tenure of fifteen years across thousands of retail locations worldwide.
• Won Overall RetailTech Innovation of the Year at the 2026 RetailTech Breakthrough Awards for KWI’s AI product image search.
• Included in Forrester’s The Point-Of-Service Solutions Landscape, Q2 2026.
• Grew the platform from point of sale alone into merchandising, order management, loyalty, CRM, Snapshot mobile analytics, AI product image search and open APIs.
• Wrapped the software in managed services — customer success, hardware support, helpdesk and global payments — plus implementation and integration professional services.
• Launched a Klaviyo connector for specialty retailers.
• Moved the company’s headquarters from Greenvale, New York to Melville, New York in 2024.

Professional Journey

The founding story is unusually concrete for a company of this age. In 1985 Kliger, nineteen years old, walked into a Benetton store, saw the queues at the register, and spent the following months writing software to make them shorter. He left school to deliver it. What he built was not shrink-wrapped software sold to a retailer to install and operate, but a system KWI hosted and managed on the customer’s behalf — the arrangement the industry would later name software as a service, arrived at here for the practical reason that specialty retailers had no IT departments capable of running it themselves.

That structural choice has defined the company ever since. KWI sells retail systems and the operational responsibility for keeping them running: helpdesk, hardware support, global payments, implementation and integration all sit inside the offering rather than beside it. It is a harder business to scale than pure software, and a considerably harder one to leave, which is the most plausible explanation for the fifteen-year average customer tenure the company reports.

The product line has broadened steadily from point of sale into merchandising, order management, loyalty, CRM, mobile analytics under the Snapshot name, and an open API layer, giving fashion and specialty brands a unified commerce stack from one supplier. The most recent addition is AI product image search, which won the company Overall RetailTech Innovation of the Year at the 2026 RetailTech Breakthrough Awards, and a Klaviyo connector aimed at specialty retailers’ marketing stacks. Forrester included KWI in its Point-Of-Service Solutions Landscape for the second quarter of 2026.

Two things stand out about how Kliger has run the company. The first is capital: KWI has never taken outside investment, which in a category where most competitors have been through private equity or trade sale is a deliberate and costly choice in growth terms. The second is durability of the executive bench — the company operates with a full C-suite covering revenue, technology and finance alongside heads of product, marketing, client experience and people. In 2024 the headquarters moved from Greenvale to Melville, both on Long Island, where the company has always been based.

Education

No formal education could be established. KWI’s own account of the company’s founding states that Kliger quit school in 1985, at nineteen, to build and deliver the Benetton system that became the company’s first product.