Previous generations of chatbots were present on company websites, e.g. Ask Jenn from Alaska Airlines which debuted in 2008 or Expedia's virtual customer service agent which launched in 2011. The newer generation of chatbots includes IBM Watson-powered "Rocky", introduced in February 2017 by the New York City-based e-commerce company Rare Carat to provide information to prospective diamond buyers.
“Beware though, bots have the illusion of simplicity on the front end but there are many hurdles to overcome to create a great experience. So much work to be done. Analytics, flow optimization, keeping up with ever changing platforms that have no standard. For deeper integrations and real commerce like Assist powers, you have error checking, integrations to APIs, routing and escalation to live human support, understanding NLP, no back buttons, no home button, etc etc. We have to unlearn everything we learned the past 20 years to create an amazing experience in this new browser.” — Shane Mac, CEO of Assist