4 Neglected Truths About Live Chat For Start-ups

3 min read

If you’ve been hanging out anywhere near B2B marketing circles the past few years, you couldn’t possibly have missed it - live chat, modern messaging apps, conversational marketing - call it what you will.

It’s a space that’s on fire in 2018.

Fueled by companies like Intercom and Drift, the live chat battleground has become the new darling of the marketing technology world with countless start-ups and established companies from Hubspot to Zendesk jumping into the ring.

Live chat tools come with the promise of completely changing your approach to marketing, of revolutionizing the way you deliver customer support, and there’s even companies like Swayed that are building live chat tools with the goal of replacing sales reps altogether.

The rise of live chat is a good thing for B2B buyers and B2B sellers - it’s a direct response to the way people have increasingly chosen to communicate over the past few decades. From AOL Instant Messenger, to texting, to HipChat and Slack, chat based tools are the new normal and it’s a good thing that this is finally being translated into the B2B world.

But the good almost always comes with some challenges, particularly for the end consumer. I remember sitting at my desk back in 2010, just knowing I needed a marketing automation platform and trying to make sense of the differences between Hubspot and Marketo. Both were making a lot of noise online. Their sales reps were slick and convincing. And somewhere in the midst of all those shiny features I still found myself wondering…

“How exactly am I going to use this product in the course of my day to day job?”

Today’s buyers face similar challenges; there is a deafening amount of noise in this space at the moment. This post is for start-up companies who are thinking about live chat, trying to figure out how this channel fits into their technology stack and how it can be best leveraged at their company. My aim is to surface some sensible and often neglected truths about live chat so that you can see through the hype and make smarter decisions about how you can best leverage live chat at your start-up.

Live chat products are not new

Marketing technology vendors are notorious for creating hype; a bi-product of these companies competing for the attention of buyers alongside nearly 6,000 other companies. Pile on the growth expectations that come with the amount of venture capital that’s been poured into this space (Intercom and Drift alone have raised a collective $347M to date), and next thing you know live chat tools are being presented as something new.

Point blank, they’re not. So what is new?

First, the user adoption of these technologies has continued to grow; this market has long been sizable, but it’s continuing to expand. Second, the aforementioned VC dollars that have been poured into this space have cranked up the volume and noise around all things live chat.

A few examples to prove my point - LivePerson was founded in 1995 and IPOed just 5 years later in April of 2000. LiveChat Software has 21,000 customers and was founded back in 2002. SnapEngage was founded in 2008, and Olark was founded in 2009. Heck, software review site Capterra has over 238 live chat products listed on their site.

The point is, this means of engaging with customers whether it’s on your website, in your app, in a sales context or a customer support context; it’s been around for quite a while already. These tools are now more commonplace, but one could very easily argue that this was simply an underutilized means of engaging with prospects and customers previously.

Beware the vendor who sells you the hype; seek out the companies that will spend their time educating you on how to make the most of this channel. You have many, many good options to consider.

Live chat is notorious for creating lousy customer experiences

In order for live chat tools to really provide value - to become that engaging channel where website or product visitors can go to get truly personalized, on-demand answers to their questions - someone needs to be available.

The truth of the matter is staffing live chat appropriately is very similar to staffing a call center appropriately - it’s just not very sexy to say that. If nobody’s there to pick up the phone when you call in for help and you’re put on hold for hours on end, it turns what could have been a positive interaction into a really negative one. Frustration boils, patience is lost, and people move on.

We’ve all been there with live chat too - you ask a question, you get radio silence. Or worse yet, you get an autoresponder asking you for your email address. That’s the equivalent of walking into a brick-and-mortar store where there’s no one available to check you out, but there’s a sign-up form at the checkout register so you can sign-up to receive the store’s catalog in the mail.

This challenge is particularly tough to solve for start-up companies; while bigger companies likely have dedicated support or sales staff whose primary responsibility is to monitor incoming chat sessions, most start-ups don’t. Even with desktop notifications of incoming chats enabled, start-up founders are often trying to juggle responding to chat messages with their other responsibilities. If you’re in the midst of writing code, or conducting a product demo, or meeting a potential hire for coffee that incoming chat message is going to get put off.

Next thing you know you’ve turned off another prospect.

Think long and hard about whether you can truly staff live chat appropriately as a start-up company. It’s totally OK to say “not now” to live chat; maybe asking site visitors to submit a support ticket with the promise of a response in 24 hours is more appropriate for your stage. Whether you decide to leverage live chat or not, expectation setting with visitors is key - don’t be afraid to use live chat away messages liberally if they help you set expectations appropriately and avoid turning off site visitors in the process.

“It’s totally OK to say “not now” to live chat; maybe asking site visitors to submit a support ticket with the promise of a response in 24 hours is more appropriate for your stage.

Bots are the very definition of providing impersonal service

As you read the previous paragraph about the challenges of staffing live chat appropriately, I could almost hear you calling out, “But there’s a solution to this problem! It’s bots!”

To which I say, please, beware of the bot.

If you’re bot aware of what I’m talking a-bot, bots are essentially autoresponder tools that use natural language processing to understand some aspect of what they’ve been asked through a live chat interaction. They then use this understanding of what they were asked to surface useful content that answers the question or routes the conversation to an appropriate person if someone is available.

You know what bots sound like to me? A phone tree. “Say one for sales, two for support.” This workflow isn’t new, it’s just wrapped in shiny new technology and packaging.

“You know what bots sound like to me? A phone tree. “Say one for sales, two for support.” This workflow isn’t new, it’s just wrapped in shiny new technology and packaging.

If we’re being honest with ourselves, I’d argue this similarity is undeniable. What many live chat vendors really don’t want you to know is that bots represent cool new technology that helps them attract software developers who are interested in working with these technologies.

I know, I know, I’m being particularly hard on the bot. In the vain of fairness, I’ll say this; there’s a reason so many companies are employing them. They can help route conversations appropriately. They can be available when a real person is not. They can accelerate sales cycles. All good things.

But the crux of my argument is the bot doesn’t really serve the customer, it serves the company employing the bot. If you truly believe in being customer centric, in putting the customer first, is routing someone’s question to a bot really the best way to deliver a delightful experience?

I would argue that it’s not.

Nobody has ever really wanted to chat with a bot, so if world class service is your objective have someone available whether it be by phone, via email, a live chat tool, or any other means of communication. If you think about it, there couldn’t be anything less personal than talking to a bot, could there?

You must contextualize your greeting messages to the content of your web pages

This final point is so often overlooked in the context of live chat discussions, it’s absolutely dizzying to me. Most live chat tools provide users with ability to prompt new website or app visitors with a greeting message (a proactive strategy designed to start conversations), or allow the visitor to initiate a conversation by clicking on a live chat icon, usually in the bottom right hand corner of their screen (more of a reactive strategy).

There’s a time and place for both.

What I see entirely too often is companies choosing the proactive path, but popping up the exact same greeting message on all of their website pages.

Home page: “Hi there, I’m here if you need any help. Please enter your email address in case we get disconnected.”

Features page: “Hi there, I’m here if you need any help. Please enter your email address in case we get disconnected.”

Pricing page: “Hi there, I’m here if you need any help. Please enter your email address in case we get disconnected.”

Again, this quickly becomes a nuisance and next thing you know your live chat tool is actually driving up your website’s bounce rate.

The good new is there’s an easy answer here - contextualize your live chat tool’s greeting messages to the content of the web page on which the message will display. If you have a website page that talks about email marketing, prompt site visitors by asking them a question about what they’re doing to increase their email open rates. If you have a web page that details all of the features of your company’s billing solution, ask site visitors how they’re charging their customers today.

In all of my experimentation with live chat tools, nothing has increased conversations or the value of the tool in general more than crafting custom greeting messages that fit the context of the page’s content.

For today’s buyers, there’s one problem that’s unfortunately prevalent; many live chat tools require you to upgrade to a higher pricing tier that’s unaccessible to start-ups in order to use custom page-specific greeting messages.

Unlocking “advanced” functionality in higher pricing tiers is the norm in the marketing technology world, and it’s very much a logical pricing strategy. But when vendors hide core functionality that’s really a must-have in order to have success with their products behind a massive price tag? That’s evidence of a growth-at-all-costs mindset and it’s ultimately the end consumer who loses.


Live chat is an increasingly in-demand means of engaging in the B2B world and can be really effective in helping companies communicate with their customers and prospects in real-time, on their terms. But like any new software trend, make sure you’re not blindly following the masses like a lemming off of a cliff. It takes careful consideration of your availability and your ability to contextualize your live chat experiences to deliver truly positive and personalized conversations that delight your customers.

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Miguel Bain

March 19, 2023

Great advice about contextualizing the greeting messages to the content of the webpage. Never thought of that before. Thanks a lot for sharing that idea! 👍 Do you use any sort of specialised software to analyze all the data you receive from your customers? When I was working in a call center in NYC we had wonderful soft from https://voiso.com/ which afterwards gave us a really profound analytics and managed even to record calls with 95% recognition.