Facebook Faces Hurdles in Messenger Push

Customers of clothing maker Everlane might have seen a promotion for free two-day shipping just days before Christmas in an unusual place: Facebook’s Messenger app.

For months, a handful of companies such as Everlane, children’s clothes maker Zulily and Hyatt Hotels Corp. have captured attention by fielding customer service questions and giving updates on purchases in Messenger. But Everlane’s advertisement in the messaging platform–similar to a free-shipping email that could wind up in your spam folder–shows how businesses using Messenger are starting to try and flip those friendly customer interactions into prompts to buy more goods.

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But the technology might face at least initial skepticism from some consumer businesses there, too. “It’s too far in the future to talk about AI. We’re a company of people. You’re talking to real people when you talk to us on social media,” said Ashley Mainz, the social business manager for Southwest Airlines.

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“As soon as we overstep that boundary and send them discount codes, they won’t follow us...That, for me, will make people not want to have conversations with brands on Messenger."