IBM Watson is learning the same lesson that so many American workers have learned in the modern era: In the course of a lifetime, you are likely to have multiple careers.

Watson, of course, has had storied careers as a “Jeopardy” champion and a medical researcher (including veterinary medicine apparently). And now the cognitive computing system is setting its sights on a retail career.

The big lug, who’s palled around with Bob Dylan in T.V ads is one of the stars at the National Retail Federation’s Big Show 2016, which opened today in New York. One of the early sessions featured Watson’s work with The North Face, which in December rolled out a feature that let’s online customers shop for coats by carrying on a typed conversation with Watson, the way they might converse with a sales person when they go into a store.

In a way Watson is an appropriate celebrity face for this week’s trade show. He represents two of the key characteristics of retail now and into the future. The first is the need to provide one-to-one personalization for shoppers. The second is the wisdom in combing  humans and machines to tackle the personalization problem at large scale.

(More on Watson’s place in personalization.)

That said, being a celebrity isn’t always easy. In his work with The North Face, Watson encountered a problem common to many famous folks: His reputation preceded him.

More coverage of NRF’s Big Show 2016

“The system requires a lot of teaching,” Cal Bouchard, The North Face’s senior director of e-commerce told the crowd during a Sunday morning session on Watson. “As an AI (artificial intelligence) newbie, I thought, ‘Oh, Jeopardy champion. Watson. I’m going to get that. I’m going to get this thing that beat Ken Jennings and has all the information in the whole world already built in. Not true.”

It is going to take time for Watson to do all the things Bouchard wants him too, but she said she’s taking the long view. After all, the best solutions often aren’t the easiest solutions. For now, the Watson feature works only for coat shopping and it is better at asking questions (and modifying results based on answers) than it is at answering them.

I used Watson to shop for a coat for a trip to Chicago in February. It’s top recommendation was a spiffy model in the color I told Watson I liked, but it cost $399. When I asked Watson if he had anything cheaper, like a good commission sales person he said: “I don’t understand what you mean by ‘cheaper." 

IBM Watson

But so it is with developing technology and developing uses for it. Bouchard is willing to wait. (She also knows something about celebrity and expectations, having been co-captain of the 2000 Canadian Olympic basketball team.)

“We’re always looking for ways to engage the consumer that may not be the quickest hit to purchase or conversion, but maybe a long-term play,” she said.

And she sees a day when Watson will not only be making product recommendations, but also providing ski tips for those buying ski jackets and offering travel suggestions for those who mention that they’re buying a coat for a trip.

“We’re just at the beginning of looking at how AI technology can really apply to retail,” added Neil Patil, of digital agency Fluid, who presented Sunday with Bouchard. “ We know that AI technology is going to be huge. And it’s huge that we consider that in the retail industry.”

Watson exhibit photo by Edward Blake published under Creative Commons license.

Mike Cassidy is BloomReach’s storyteller. Contact him at; follow him on Twitter at @mikecassidy.