Nikki Yanofsky, a 16-year-old jazz-pop singer, will appear in a series of webisodes and digital ad units for Winners in a new back-to-school campaign. In the ‘Wow Canada and Win’ promotion, the retailer asks shoppers to submit a video, song or photo that best exemplifies their talent on the Winners Facebook page, which has about 150,000 fans.

The contest opened just last week, but already about 30 videos have been uploaded of youths playing guitar at school, or singing Justin Bieber cover songs in their bedrooms. The grand prize is about $7,500 plus hang-out time with Yanofsky.

Arranged by MediaCom, the campaign aims to enagage youths aged 12 to 24 during the back-to-school shopping season. Ads promoting the campaign will run as in-unit and 10-second pre-roll executions on Yahoo.ca, YouTube.com and Windows Live Messenger, as well as Facebook videos and webisodes starring Yanofsky, polls and fanning units. A Winners insert will also appear in Yanofsky’s CD units sold in the retailer’s chain of stores – but even that has a digital component, explains Anthony Hello, director of content at MediaCom.

‘This is definitely a digitally based strategy – even the inserts on the CD drive to online with a song redemption,’ Hello tells MiC. ‘We purposefully took a chance and said, you know what, we’re targeting youth, we’re going to go to exclusively online with this.’

The partnership with Yanofsky, who will also appear on the Winners fall Fashionomics mailer sent to more than a million homes, is part of a long-term strategy of using music as a connection point with teens. But the jazz singer, who has an unusually mature voice, also appeals to parents who do much of the buying, says Hello.

‘For the past couple of years, we’ve pursued a music-based strategy. In the past we’ve worked with MuchMusic, MTV and MusiquePlus in Quebec, but this is the first time that we’ve engaged a celebrity face. With the choice of Nikki, we cover English and French Canada,’ he says.