Decades ago, long before “couponing” became an official word, I recall that my retired grandparents had already made it into a sport. Every Wednesday they bought multiple copies of the local newspapers, because it was coupon day. This was not penny-pinching or saving by retirees with limited budgets. In fact, my emigree Italian grandfather had been an American success story – retiring with a bakery business and owning three apartment houses. Coupons were something deeper for this couple. They sat on either side of the kitchen table (headquarters in any Italian-American household), and they recited to each other what coupons they were finding, whether to clip it, and who in the family would need it. They were providing for an extended family of children and grandchildren, and not to mention scores of paisanos in nearby Patterson, N.J.. When I was in college and grad school, living on a thread, Grandma sent me packets of coupons of the foods she knew I liked. Who knew that coupons could be turned into emblems of love and attentiveness? Of course when Grandma and Grandpa passed, they had in their basement more bottles of Tide laundry detergent, Brawny paper towels and mac ‘n cheese boxes than most A&Ps. There is a fine line between coupons as family ritual and pathological hoarding, apparently. Today the channels through which consumers can capture coupons have broadened considerably since the Wednesday and Sunday newspapers -- but I'm not sure it is quite as easy to apply my grandparents' dedication to “couponing.” As a non-couponer, my only encounter with these promotions is that thick blue direct mailer from Valpak that I used to rifle through in front of the TV in the days before I had an iPad to serve as my prime-time distraction. But in recent weeks the Valpak started showing up in one of my standby mobile apps, CheckPoints, a check-in and rewards app for nearby businesses. “In mobile vs. the Web, we see greater redemption rates in mobile,” says Fred Steube, Digital Innovation Director, Valpak. “We are seeing increased use of mobile coupons and increases in redemption.” “Our strategy in mobile is to be platform-agnostic,” says Nancy Cook, VP Digital Business Development, Valpak. Its mobile Web site that just relaunched and their apps are slated for relaunch next month. “Out app downloads tripled last year,” she says. One of the company's more interesting partnerships is with with the augmented reality browser Metaio provider. When you launch the Junaio app and apply the Valpak overlay (all in branded blue, by the way) you can aim your phone around the neighborhood to pick up the local deals. In the case of a rewards app like CheckPoints, a partner such as ValPak can add value by giving CheckPoints members an opportunity build rewards points by checking in with local businesses. Cook says that Valpak deals are distributed digitally to over 150 sites as well. In all of these cases, the company is providing a daily feed to the partners so the coupons and offers are updated regularly. As with all mobile advertising and marketing in the digital age, expect a familiar turf war over trying to capture that small business and local service owner that has eluded digital for so long. Incumbents like Yellow Pages, local newspapers, local TV stations, free circulars and coupon mainstays like Valpak all lay claim to having these local clients already on board with traditional media. But getting them into the digital, let alone mobile, mainstream is fraught with challenges. Valpak’s current cross-platform clients can get into this feed of mobile offers by default, so whatever you get in that weekly packet in the mail may also show up in CheckPoints or in Junaio. Which doesn’t mean that when you try to bring your smartphone into the merchant the clerks know what to do. “There are operational issues,” Cook admits. “Merchants are still trying to understand how to redeem and what to do with mobile coupons. The education process is the biggest hurdle.” And so Valpak provides the local clients with point of sale material so their cashiers can recognize a mobile coupon when they see one. There is a unique ID in the coupon to prevent fraud. Mobile coupons are a no-brainer. Not having to clip, save and remember to carry print promotions is a convenience that should in theory supercharge the coupon format. But apparently it will take some brains to figure out how to execute on the promise. Complexity and clutter is something startups thrive on. Thrusting that same sensibility onto Main Street jewelry stores and roofers is a non-starter. The old familiar sales channels like directories, newspapers and folks like Valpak have an opportunity to educate their clients, but mobile offers up new and unfamiliar redemption problems that even printable digital coupons did not. In the decade and a half I have been covering digital media, I lost count of the many schemes I have seen to coax local SMBs into digital marketing. It is unclear to me how successfully that transition really has taken place despite the effort. I don’t envy the shop owner having to figure out what manner of discount this fellow with the Galaxy II S is trying to pawn off on him this time. And how about that high schooler or the owner’s daughter running the register on Saturday afternoon? They are more anxious about making a mistake than they are in making the digital promotions eco-system flow smoothly for us all. My guess is that the road to mobile coupon redemption will require concerted effort at the end point of sale. In many ways the digital marketing industry has continued to defer this problem. There is a persistent mismatch between the kinds of businesses, technology and sensibilities that drive digital marketing and those that run local businesses. Until now local businesses could hand off their digital programs to others or just ignore the channel altogether. With mobile, however, that complexity, fragmentation, unfamiliarity comes right into the shop when the slick guy with the iPhone gets impatient with a checkout girl at the general store trying to figure out what Mr. iPhone is trying to show her on his barely visible LCD screen.