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Descartes was founded in 1981.
In 1998, the company made an initial public offering on the Toronto Stock Exchange, where its common shares traded under the stock symbol DSG. Descartes was first listed on the NASDAQ Stock Market in 1999, with common shares trading under the symbol DSGX. Descartes’ share price peaked during the dot-com bubble in 2000, and then fell precipitously in the subsequent crash.
In 2001, Descartes switched its business model from selling full-featured enterprise software licenses to providing on-demand software on a subscription basis, becoming one of the first SaaS providers in the logistics sector. After years of losses, Descartes came close to bankruptcy in 2004, prompting it to aggressively restructure. The company cut 35% of its workforce and initiated a sweeping transformation of its corporate culture under CEO Arthur Mesher, who was appointed in 2005.
The company returned to profitability in 2005, with Difference Capital Managing Director, Tom Liston, describing this as "one of the most dramatic turnarounds in Canadian corporate history."
In December 2013, Descartes was added to the S&P/TSX Composite Index, an index of the stock (equity) prices of the largest companies on the Toronto Stock Exchange.
By January, 2015, Descartes had posted 41 straight profitable quarters and was supplying logistics software and services to more than 10,000 logistics-centric businesses, such as ground transportation companies, airlines, ocean carriers, freight forwarders, manufacturers, distributors, and retailers. Its customers included American Airlines, Delta Air Lines, Air Canada, British Airways, Maersk Group, Hapag-Lloyd, Con-way, Kuehne + Nagel, DHL, The Home Depot, Sears Brands, Hallmark Cards, Hasbro, Volvo, Ferrellgas, Del Monte, Toyota, and The Coca-Cola Company.
In 2018, Gartner ranked Descartes 6th in its list of the Top 20 Supply Chain Management Software Suppliers, based on revenue of $221 million.
In 2025, Descartes was also recognised by the ARC Advisory Group as the leading provider of cloud-based Transport Management Systems (TMS) and the leading provider of fleet management applications.
As of 2025, 5 Descartes products are recognised in the Top 50 Supply Chain & Logistics Products list on G2, and the company is recognised as the #1 Grid™ Leader in 12 categories.