Jason Del Rey

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With Alibaba Investment in ShopRunner, CEO Scott Thompson Gets His Second Deal With Jack Ma

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ShopRunner, the two-day online retail shipping service that aims to compete with Amazon Prime, is close to landing a large investment from the Alibaba Group, according to sources that confirmed reports, including one in The Wall Street Journal.

The two sides have been discussing a deal to invest more than $70 million for a minority stake in the company, which offers free two-day shipping at dozens of retailers to its members who pay $79 annually. The investment would be important to Alibaba, which has been investing in a range of companies as it seeks to compete more aggressively against Amazon.

And it’s a nice chunk of change for the startup, of course, but perhaps the most interesting aspect of the possible investment is that it would mark the second agreement with the powerful Chinese e-commerce company for Scott Thompson, the current ShopRunner CEO and former Yahoo CEO.

As many know, Thompson left Yahoo under a cloud, after the controversy over inaccuracies on his resume forced his departure from the Silicon Valley Internet giant.

But before he departed he was one of the key dealmakers in the major Yahoo agreement with Alibaba Group, in which it sold back half its stake and got billions of dollars in return. While the transaction was announced after Thompson was ousted, there was no question that it left new CEO Marissa Mayer with a huge cash kitty that she has used to go on an aggressive acquisition spree, and it also complete a massive share buyback program.

Those moves, along with the continued appreciation of the Alibaba stake as it moves to an IPO later in the year or early next year, have been key factors in pushing Yahoo’s stock price into the high 20s, even though its core business continues to lag.

While some think that Yahoo sold that partial Alibaba stake too early, it is easy to forget how acrimonious the relationship was, and how Yahoo itself was also in play in an increasingly fraught investment environment. The striking of the deal with Alibaba was one of the first signs of true stability at Yahoo.

And there is no question, especially to Alibaba, that Thompson deserves some level of credit — along with many others, of course — for landing the deal.

Since he left Yahoo, Thompson has kept a low profile. Now, with a large injection of cash from his friends at Alibaba, Thompson and ShopRunner may become a bit more high-profile after all.

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— Valleywag editor Sam Biddle