Among the rash of high-level executive changes that have swept through the discount and drug store sectors in recent weeks, none is arguably more important for the future of the company that made it than Sears Holdings’ appointment of Tesco executive Alasdair James as Kmart president and chief member officer.

Among the rash of high-level executive changes that have swept through the discount and drug store sectors in recent weeks, none is arguably more important for the future of the company that made it than Sears Holdings’ appointment of Tesco executive Alasdair James as Kmart president and chief member officer.

On paper, the pairing of the struggling discounter and James, who has also held executive positions at GlaxoSmithKline and PepsiCo, appears to be a good fit. During the past seven years at Tesco, which despite recent setbacks is still the world’s second-largest retailer, James rose to become executive vice president and commercial director of the British company’s operations in China and, ultimately, director of its extensive international business.

"Alasdair will work closely with me and our business unit leaders to understand the preferences of Shop Your Way members," says Sears Holdings chairman and chief executive officer Edward Lampert, referring to the social media shopping platform created by the company that offers rewards to members for patronizing Kmart, Sears and other participating retailers. "He will be responsible for the Kmart strategy, its performance and its continued transformation as an integrated retail format."

Two factors make that a particularly challenging assignment: Kmart, which only a generation ago was the dominant mass merchant in the United States, has seen its standing steadily erode in the ensuing years, a process that the merger with Sears engineered by Lampert in 2005 did nothing to ameliorate. To reverse such a long, downward spiral and the culture that has resulted from it will be a severe test for James, a newcomer to the American market.

An even bigger obstacle to the revitalization of Kmart may be Lampert himself. Founder of ESL Investments, a large hedge fund, Lampert has proven an adroit investor and businessman, but his record as a retailer is far less impressive. He has failed to develop a strategy to stem the decline of two of America’s iconic brands during almost a decade in control of the company. Worse still, Lampert has frequently ignored or overruled the seasoned retail executives he brought in to help put Sears and Kmart back on track.

The hope here is that James will be given enough leeway to apply what he has learned at Tesco to Kmart’s turnaround efforts.