Next time you're shopping online, be prepared for a chat.

As live chat technology evolves, e-commerce sites are finding that virtual clerks are becoming crucial to customer support and sales systems. Earlier this year, Bold Software, a live chat and click-to-call service based in Wichita, Kansas, polled 200 of their customers—mostly online merchants who use the software to interact with customers browsing their sites—to see just how effective live chats really were. Twenty three percent reported conversion rates among chatters of at least 40 percent; 54 percent reported a conversion rate of 20 percent or more. In fact, 77 percent of the respondents even said that live chat was "critical" to the success of the company.

Fan Bi, co-founder of the Boston-based clothing start-up Blank Label, says we've just scratched the surface of what live chat can do for an online business. Previously, e-mail and phone presence were essential for customer service, but now it may be worth it to focus on live chat.  "This is more native to the way that we're behaving online," he says. "You used to have to call in to ask about anything. Then it was email. This is just the least amount of work for the customer, and I think it's becoming a really interesting movement in e-commerce and customer service."

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How to Use Virtual Sales Clerks: Learn About Your Customers

Just because your customer doesn't buy something, doesn't mean you can't learn something about him or her. Fan Bi, for example, says he'll talk to customers on his site throughout the day to understand why they came to the site, what they're looking for, and who they are. Instead of persuading them to buy one of their custom-made dress shirts, Bi just takes the opportunity to have a friendly conversation.

"Sometimes you'll have several lines of chat, and we'll ask if they usually wear dress shirts to work ever day, or just more of a casual thing," he says. "It's about customer profiling and understanding who the customer is—things that they wouldn't explain to you in an email. You learn more about the customer when it's just an informal chat."

Once you get into the swing of chatting with your customers, it's not uncommon to make friends with a few of them. Noah Kagan, the founder of, a discount digital marketplace, says he even keeps in touch with some of his site's visitors after they leave. "People start talking and it's so hard not to talk to them," he says. "The people who come to my site—they're my customers, they're stopping by my party. So we start chatting and I ask them what they're working on." Recently, Kagan says he exchanged Skype addresses with a visitor to his site. 

How to Use Virtual Sales Clerks: Personalize 

The key to a successful live chat conversation is personalization, says Jerome Mouton, the founder of SnapEngage, a live-chat start-up based in Boulder, Colorado. The company, a 2009 TechStars alum, has a unique approach to personalization: When you receive a chat from a SnapEngage representative, you'll see a picture of the representative as well as their real name.

"We think the personal relationship is critical from the start," says Mouton. "We encourage our customers do the same. It's been our approach from the start—when you have a little pop-up that you know is something automated, people just close it. But when someone is there and talking directly to them, they feel more obligated to at least say 'Oh no thank you I'm fine." The conversation doesn't necessarily end there. "When they say that, it's also an opportunity to say something else like 'OK, well let me know, I'll be around."

The goal of live chat is to simulate a retail store where someone walks in and is greeted by a customer representative, says Mouton. Even if the customer doesn't need assistance, the customer will be reassured that there's someone available to them.

"You just don't want them to feel lost," he says.

Noah Kagan, founder of, says his customers sometimes get impressed with the fact that he himself jumps onto the chat—and that the company's founder, not an outsourced virtual assistant—is helping them. "I think they're surprised that I'm the founder," he says. "They feel a little bit special. If I could do that most of the day, I would. It's very rewarding."

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How to Use Virtual Sales Clerks: Be Proactive

There is a significant amount of nuance to how you ultimately decide to structure a live chat account. Some services let users click an icon to chat with a representative; others initiate the conversation with the customer directly. Fan Bi says he ultimately chose a more proactive approach for two reasons.

"First, I had horrible live-chat experiences where there would be a pop-up in a different window and you have to put in your name and e-mail, and there was just a lot of friction, going back and forth between two windows," he says. "It wasn't a very good experience. The first part is keeping it inside the browser. I think that makes the experience a lot better."

Secondly, and perhaps more importantly, is about being proactive. "Like going into the Gap, after browsing, if no one comes up to you and asks if you want help, you'll leave," he says.

Being proactive will also allow you to troubleshoot why customers aren't buying a certain product. Kagan, for example, says he's been able to resolve some issues in near real-time; other recurrent issues can be addressed going forward in an FAQ page. Recently, Kagan says that customers weren't sure how much time they were given to redeem the product after it was purchased.  "I would have never known that was the problem by sales data or just talking to random people," he says.  "Now there's a thing that says you can buy today and use it when you're ready. That's directly from live chat."

He adds, "If I could have live chat for every person who visits my site, I would do it. It's that valuable. People are just so surprised. They get the instant gratification. I can't tell you how many times people told me that they'd buy because of the chat. It happens all the time."

How to Use Virtual Sales Clerks: Don't be Pushy

Jerome Mouten, SnapEngage founder, says that people are generally more willing than they were 10 years ago to chat with a customer service representative. "The technology is not intrusive," he says. "If you don't want it, you close the window, and we don't bug them for one full hour. If they come back the next day again, they'll see it again."

Fan Bi says it comes down to the type of customer. Most tend to ask if he's a robot or a real person; other times they'll ask if he's outsourced. Though conversion rates are actually low, Bi says live chat has been extremely effective in understand his customers more clearly. "It's kind of a male thing," he says. "You know, we like to find the answer ourselves. But it's easy enough to click off, and it's not enough of a turn off."

He adds that with live chat, "We can help them with things that they would have otherwise just exited the site because of...I think that's a massive advantage. I think it's helpful in getting more sales and pushing people to buy."

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