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Demand Gen, Sales Tools

How to leverage Live Chat & Chatbots for Lead Generation

Jacco van der Kooij

Written by Jacco van der Kooij

Founder, Winning by Design


 Live Chat & Chatbots for Lead Generation


Outbound Prospecting Is Suffering

The world of outbound prospecting is not doing too well. Companies are consistently reporting that results from outbound are getting harder to attain. Low conversion rates from email sequences are creating more noise than actual results. GDPR regulations are making traditional outbound prospecting tracks even more challenging. As a result sales managers are finding it increasingly difficult to find and motivate SDRs who have to operate on daily basis in these troubled grounds.

Figure 1. Decline of number of Sales Qualified Leads generated per month per Sales Dev Rep.

Figure 1. Decline of number of Sales Qualified Leads generated per month per Sales Dev Rep.

Not just the volume but also the quality has decreased causing rampage in many sales organizations as teams no longer are able to hit quota.

Figure 2. Typical SQL attribution within SDR Teams

Figure 2. Typical SQL attribution within SDR Teams

That said, we still need to grow our companies. The big question is how we will compensate for that loss of lead generation potential. Where are those new untapped goldmines? We?ve seen SDRs achieve great results prospecting through video. Other teams are having more luck finding fresh leads through review platforms such G2Crowd & Capterra. The craziest one I?ve seen recently was the SaaS company Intuo quite successfully reverting back to personalised print mail campaigns. Oh yes, print!

Before reverting to new outbound methods there is one way of finding leads that is too often overlooked: Inbound via website chat. These leads are already there but are just not being converted.



Understanding Chat

What makes website chat so powerful for prospecting? There is one thing in common that the other prospecting methods are not nailing to the nitty-gritty details: impeccable timing. It?s that simple. Website chat leverages that exact moment where prospects are engaged and most willing to start a conversation: those couple of minutes when they are navigating your website. Does the following phrase sound familiar? ?I don?t have time for this right now.? This is the usual answer you get after visitors have left your website. Most prospects would actually love to engage, but only when you have the timing exactly right.

That level of customer centricity is worth looking into. Several SaaS companies are already reporting website chat as their biggest lead source and others are reporting over 50% of leads coming through the website chat (source). Chat providers like Drift & Intercom are leading the way by banning most forms from their website and rely on their chat tool to find their lionshare of leads. Agreed, this is a strategy that inherently promotes their product but it seems to be working extremely well for them.

Figure 3. Traditional Process compared to the Expedited Chat Process

Figure 3. Traditional Process compared to the Expedited Chat Process

First and foremost, conversing through chat shortens your sales cycle. The moment a prospect leaves your website after leaving his email address in a form his focus goes to the next problem of the day. In a traditional process it?s now it?s up to the SDRs to reach out to these prospects in the hopes of getting a call or demo booked. That?s when the process becomes lengthy and difficult because the prospect has left his engaged mindset. Prospects are much more willing to start a conversation the moment their mind is set to discover that product, which is during a website visit. That key moment needs to be leveraged right then and there to start a guiding conversation leading to a demo. Striking when the iron?s hot simply evokes great speed.

Secondly, it will result in a higher Visitor to SQL conversion. A large portion of your website visitors who might buy your product / service are not finding their way to a contact form, demo request, or an inbound email. They are just not triggered enough to take that action. That?s where a conversation is essential to help them get to that point. Without a chat these prospects would just vanish into thin air and be lost forever. Your SDR team can immediately benefit from the ability to take control over that process and help these people to a meeting.

Finally, visitors will be left with a better experience. Some website visitors will never buy: visitors with no buying fit, students, job applicants or existing customers. The impact of having a website chat is the ability to detect these individuals early enough in the process and make them leave with at least some value. This to make sure your sales reps are not wasting time chasing disco calls and demo?s for these people and could create some ambassadors in the process.

Figure 4. The impact of online Chat on website visitors.

Figure 4. The impact of online Chat on website visitors.




?We?ve tried having a chat on our website but it didn?t really work so we let it go.? -?Many sales leaders today


Unfortunately, this is something I heard from SaaS sales leaders on several occasions. When digging deeper soon comes the realisation that the experience created was far from great. In worst cases, it looked much like the process of calling customer service of your telecom operator: long waits, getting redirected, having to repeat your story and difficult to get the answers you?re hoping for. It is often the most junior person of the team is in charge of website chat, among the 17 other tasks he or she is asked to do. Occasionally, junior sales reps are doing a remarkable job but the lion-share fails to succeed. The best way to compare a qualitative online chat is to having a team of lobby people much like the one led by Gustave H. in ?The Grand Budapest Hotel?.


?A lobby person is completely invisible yet always in sight. He remembers what people hate. A lobby person anticipates clients needs before the needs are needed.? – Gustave H.


A good chat operator works in the same way as that five star lobby person. Always in sight but not in your face like a cold call or a mediocre outbound sequence. Always ready to jump in and always looking to guide visitors that are staying in their hotel… or navigating their website. In order to create your Grand Budapest experience there are 4 criteria you need to nail:

five star


First things first. We need to get our website visitors actually engaging with our chat to make this?work. We initially thought that visitors would be more willing to engage with a human than a bot. Sound logical at first right? The opposite is true. When we replaced the human chat widget to a bot widget we saw a 3x increase in conversion rate. The key thing to do is to push an automated question that is really easy and attractive to answer. The only thing the visitor needs to do is click one of the proposed answers. If orchestrated correctly, we have measured that you should be able to convert around 3%-8% of your website visitors into an initial conversation

?Surprisingly, visitors are 3x more likely to engage with a bot than a human being.??You need a chatbot to orchestrate initial engagement? -?Harold Roegiers

Figure 5. Chat bot with an easy to answer question

Figure 5. Chat bot with an easy to answer question

Figure 6. Every part of a hotel offers a different experience so to should your website.

Figure 6. Every part of a hotel offers a different experience so to should your website.

The Grand Budapest has many rooms and hallways to discover. There?s the lobby, the elevator, the pool and the restaurant. Depending on the whereabouts of the guest, the needs will be different and need to be addressed in a different way. The same story applies for your website chat. Depending on the page your visitor is navigating you can?t make the mistake of approaching them in the wrong way. Tailor your push messages, chatbot script and questions to match the visitors situation.

Figure 7. Example of Tailored Push Messages

Figure 7. Example of Tailored Push Messages

Here comes the paradox: Just a minute ago visitors were less inclined to engage with a human than a bot. After just a couple of bot engagements back and forth these same visitors welcome a human stepping in as their engagement has been driven to a higher level. Now is the time for a human chat operator to step in. Boom, you have a human conversation and the operator is ready for discovery.


When the chat operator joins the conversation the formula is straightforward: keeping your initial Time To Respond (TTR) under 3 minutes will keep you in the game but try to aim for under 1 minute in order not to miss any conversation. Hotel guests might have the patience to wait in a lobby for 5 minutes before they get help but website visitors are much quicker to move on.

Make sure to create the right environment within your team to make this work. Download a chat app on your mobile to respond while you?re on the go. Set the right mobile and email notifications, preferably with a unique sound so you know it?s go time. Link your tool with Slack so everyone in the team can engage. Organise shifts and always have at least one person responsible.

Once the human conversation has started the operator has to maintain a high speed and respond within 10-20 seconds. The visitor needs to feel that the operator?s attention is fully focused and he?s not multitasking his way through the conversation. Imagine you ask a concierge at a 5-star hotel to help you with a restaurant recommendation. And after you posed the question, they concierge without answering starts helping other customers. Eventually returning to you, and asking you another question, this keeps going on for several minutes. You would be disappointed! So to with online chat. You have to be with the customer. Keep it short, respond quickly. If you are looking up something for them. Let them know ?Hang tight? I am looking up a white paper for you on this topic.?


Chat occurs in a sterile computer environment. Add a human touch by using emoticons and balanced humor. Keep a helpful, energetic and friendly tone at all times. Have a neat profile picture up in the chat widget so the visitors have an idea of who they are speaking with. In short, simply imagine how you would like to be addressed when visiting a website. Once a visitor engages by asking a question the goal is to help them.

Avoid the 2 most common mistakes:

  1. The visitor gets asked generic sales-centric questions. Nobody likes to be qualified before they are helped. These questions typically serve the seller and not the customer.
  2. Visitors needs answers to a specific question and the chat becomes a helpdesk. The operators answers the question but lacks curiosity to elaborate on the visitors problem.

This is not good enough. Instead we?ve found that to engage a client you must ask 2 or 3 simple closed questions to know the basics of their situation. Then shift gears and ask open ended questions to better understand specific pain or challenges they wish to solve.


Last but not least you need to make sure the overall flow is designed in the most customer centric way in order to maximise your SQL output. We already know the first steps of the ideal flow:

X Maximise initiated conversations by having a bot push closed questions.

X Pivot to a chat operator to have a more human conversation.

X Finally, we need to secure the visitors landing.

Here comes the trick: after a couple of messages back and forth the realisation slowly sets in that a chat tool also has its limitations. It?s a sterile environment, typing goes slower than talking and waiting for an answer can take tens of seconds. Your visitor will feel this. This is the key moment where a smart operator should ask: ?Wouldn?t it be easier for you to continue this conversation via call right now?? Faced with the chat limitations, this proposal usually comes in as a breath of fresh air for your visitor. Ensure simplicity for your visitor by sharing a video-call link in the chat. If you succeed in doing this you have just secured a discovery call within minutes.

Figure 8. Ideal flow of a conversation initiated via chat

Figure 8. Ideal flow of a conversation initiated via chat

You could land this discovery call by proposing a demo with an Account Executive. But there is a way to take this speed even one step further. The ideal operator should be able to give them a basic demo right then and there. This shouldn?t a full on in depth demo but at least something that will get your visitor even further down his journey. If you are able to connect all these wagons to this point you have just massively crunched the length of your sales cycle.

Figure 9. Example of a good chat conversation

Figure 9. Example of a good chat conversation



This scorecard provides you with a score out of 5 to understand to what extend your organisation is leveraging the chat tool to its full potential. Score yourself against Appeal, Speed, Tone, and Flow against a 5-star rating. Today we live in a 4+ star culture.

Figure 10. Figure out your chat score out of 5.

Figure 10. Figure out your chat score out of 5.

Orchestrate this project well and your customers will greatly appreciate such a customer centric experience you just created. In turn, your sales team will be thankful for the amount of opportunities generated and be surprised of the speed at which this happens. I hope these insights were able to contribute to successfully building your own Grand Budapest experience.

Designing and implementing a successful website chat strategy can become a complex process. It’s never done. We?ve helped several companies defining a chat strategy, assisting the implementation, designing playbooks and coaching chat operators. If you?d like accelerate the process feel free to reach out to us for help.

You?re welcome to mail me at or find us via the website chat.

Harold Roegiers.

Figure 11. How a customer improved his chat score and the impact on amount of SQL?s.

Figure 11. How a customer improved his chat score and the impact on amount of SQL?s.