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Tom Jenkins, Amir Reiter, Power of Chat, Donald Kelly

TSE 991: Sky Rocket Your B2B Sales Through the Power of Chat

Tom Jenkins, Amir Reiter, Power of Chat, Donald KellyIn this episode of The Sales Evangelist, we talk about how to take advantage of the power of chat when growing your business.

Many organizations have struggled to capitalize on the power of chat, but Amir and Tom share the struggles they’ve had using chat and how we can overcome them.

Tom Jenkins and Amir Reiter help companies scale their workforce without having to get offices, pay insurance and taxes, or worry about hiring and training.

Instead, they offer technology and strategy.

At CloudTask, they provide sales development reps, they manage account executives and they manage the customer success/account reps responsible for renewals and upselling to existing customers.

They comprise one office. If someone wants to hire five sales reps, five account executives or five support reps, they will all be in office and managed so that the customer gets what they want – representation and results.  

By specializing in sales, customer success and customer support, CloudTask is the best of the breed. [00:51]

The power of chat

One of the biggest issues surrounding the use of chat is a lack of clearly defined ownership.  If you look at our partners at for instance, their ability to work as a bot or as a human can confuse whether chat is owned by marketing or by sales.

Marketing is typically used to drive traffic to forms, to blogs and to sign-ups. As such, marketing tends to prefer automation.

Sales, however, relies on people first, so deciding who owns chat is often a hurdle.

Failure to assign ownership then creates a failure to act or a failure to implement correctly. [02:19]

We manage a lot of cloud chat programs and have noticed that many people view chat as just another tool for the reps to use in addition to calling, emailing, LinkedIn, etc.

Rather, with a high volume of web traffic, chat is a key tool in the generation of qualified leads.

In fact, because chat allows you to respond quickly with the right answers and in the right way, it can be your number one lead generation tool. [03:17]

Qualify leads

People today want answers now. They expect to be able to go onto a website and to be able to chat. It has worked well in the B2C world but is really moving quickly into the B2B world as well.

We are finding that an MQL (marketing qualified lead) or SQL (sales qualified lead) that chats with a member of the sales team is 2-3 times more likely to close versus one that goes through the process of filling out a form. It makes sense. A form is stationary and available to anybody.

With chat, you are able to quickly let people qualify themselves with a friendly discussion.

For example, suppose someone wants to hire a sales rep. Within a few moments, we can discuss salaries and budgets and determine right away if it is something to pursue, or not. [04:54]

Chat conversation

Chat does not replace cold calling or emailing but it does allow the person who visits your website to have a conversation with you and determine for themselves if they want to move forward.

The desire to engage is up to the visitor. As the sales rep, you increase the level of engagement with your replies. Consider “I’m here to help sales leaders every day, how can I help you?” instead of “How are you?”

People want to work with companies that can fix their problems. Target the message to visitors as much as you can in order to increase engagement with them.

You will receive visitors who want to know more about the topic rather than starting from scratch.  

You don’t want to write too much in a chat forum, of course. Start by keeping the conversation focused on the problems you are trying to solve for your prospects. [06:48]

The initial engagement is absolutely key but response time is just as essential. Buyers are conducting research and they want answers.

It is imperative to be super sharp and to answer quickly. [08:10]

Pique curiosity

When you give visitors the information they want to the questions they ask, they begin to ask the more sales-related questions themselves.

Knowing how to give people the right amount of information so as to pique their curiosity without being overly aggressive is a skill.

For example, the best way to answer many of the questions about a technology product is with a demo. An aggressive tactic might be “this is the best product and it will solve all your problems.”

“We want you to get your eyes on this to see what you think about it” is a better approach, however. It allows the buyer to have ownership in the decision.

Chat also identifies return visitors so that you don’t have to start all over from the beginning each time. [09:42]

Sales or marketing

When Sales and Marketing are aligned as a team with the common goal of getting customers, ownership of chat is less important.

When Sales and Marketing are not aligned, better results occur when chat ownership is with the sales team.  Sales speaks to people and that brings results.

It is really important that everyone involved be 100% clear on which team does what so that each can grow and build expertise. [11:27]

Decide first if you will make your own chatbot or use a company like Drift or Intercom.

Many such companies have partner systems that can help with deployment. They are also set up to support the user and the sales cycle. It can be a big jumpstart toward a successful launch. [13:30]

Common mistakes

Some companies rely on too much automation. We’ve seen companies who don’t get the results they want right away so they just scrap the whole thing versus A/B testing people.

Everyone wants leads. It is the goal of every company but people make the chatbots and automation too much about themselves.

They try to get contact details and meetings rather than making the initial interactions about web visits. They aim to fulfill their own needs rather than the needs of potential customers. [14:25]

Chat gives buyers the ability to raise their hand, to tell you who they are and where they are in the sales cycle. It gives them the ability to get what they want now instead of going through the standard sales process. [15:28]


We have an interesting case now with a client who had used chatbot before but didn’t get the results they had hoped for. They weren’t particularly sold on the idea but were willing to give it another try.  

We were able to successfully implement a program on Drift consisting of a training program, as well as the addition of five sales development reps.

As a result, they realized $3.5 million in opportunity and $1 million in closed within eight months.

They appreciated our complete focus and specialization. We also provided them with quality assurance teams that checked in on the chats, and we worked really well together. [16:17]

We represent your company and do what needs to be done, just like employees.

The main difference is that instead of getting one new employee, our client gets a whole team. We are remote to you, but not remote. It is like having multiple offices or a satellite office.

We check on everything. [18:28]

Don’t blind yourself with the idea that you can’t use chat for enterprises.

Even if your sales process has you on flights to Hong Kong, or spending nine months working a deal, it can still start with a chat.  

Don’t consider chat as a replacement but rather as an extra channel that gives people the ability to communicate with you faster.

It can be such a cool tool to add to your cause, to your social network, and to your social ads.

When used correctly, chat will deliver results. [19:59]

“Power of Chat” episode resources

Visit Tom and Amir at or through their partners at  Allison manages their chat and is always more than happy to help everyone. Experiencing their services first-hand is the best first step.

This episode is brought to you in part by, a Chrome browser extension for Gmail that allows you to track and schedule your emails. It’s super easy, it’s helpful, and I recommend that you try it out.

You’ll receive real-time alerts anyone opens an email or clicks a link.

This episode is also brought to you in part by, a powerful sales automation platform that allows you to build highly personalized, cold email campaigns. To learn more, go to It will help you with your outbound to expand your outreach. It allows you to set it and forget it. Your prospecting will never ever be the same.

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Donald Kelly, The Sales Evangelist, Value, Questions, Listen

TSE 764-Sales From The Street-“Don’t Make Them Feel Stupid”

Donald Kelly, The Sales Evangelist, Value, Questions, ListenAs a seller, our job is to ensure we make our prospects feel comfortable with us.

During this episode, I share why and how we should help our prospects feel comfortable.

In a Perfect World

As a new sales professional, you want to get a templated script and be able to follow along. You want to know exactly what to say, when to say it, how to say it.

You just want everything laid out so you only have to follow it, thinking it’s going to work in every perfect situation.

In reality, it doesn’t work like that.

You need to have intelligent business conversations.

One of the major challenges I had when I was starting out was that I was being robotic as a sales professional.

Scripts are not bad per se, but it’s bad when you’re just reading the script and going without emotions, without connecting or understanding the person you’re talking to.

Strategies to Make Your Prospects Feel Comfortable

Don’t make your customers feel confused or look stupid.

When you’re just reading off the script and you have no emotion built into it, that would make them think you’re stupid.

Have a business conversation.

Don’t just ask rogue questions to the customers that don’t necessarily make sense to the customer because you didn’t do research on them.

First, understand how your customers are making money. What are the challenges that cause them to not make money?

Try to research on their industry to get a better understanding. That way, you’d know how to move the needle and have a business conversation with them.

Educate your customers and have meaningful conversations. As Donald Miller says, “A confused customer will never buy.”

Episode Resources:

Building a Story Brand by Donald Miller

Check out the TSE Hustler’s League.

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Ben Settle, Donald Kelly, The Sales Evangelist Podcast, Jim Camp, Start With No

TSE 379: Sales From The Street-“Let Them Sell Themselves”

Ben Settle, Donald Kelly, The Sales Evangelist PodcastBuilding a vision, repelling the wrong people to attract the right ones, and effective emailing strategies – these are just a few of the interesting topics discussed in our show today as we engage in a meaty conversation with Ben Settle.

Ben Settle specializes in email copywriting and is the genius behind the Email Players Newsletter. Today, he shares with us great insights that he learned over the years and that he’s continuously applying to set himself apart from what everybody else is doing.

Here are the highlights of my conversation with Ben:

Selling techniques Ben is learning from Jim Camp, the most feared negotiator:

No hard closing, manipulative tactics, or clever phrases

  1. All about building vision: Vision drives decision

Get in their world, give them a vision of their problem, and the sale gets in the right frame

  1. The best negotiators never create objections.

Instead of telling the feature and benefits, ask questions first to dig into the problem

Frame your questions in a way that gets people to think differently.

  1. You cannot take someone’s right to veto.

Always give them the right to say no. Ask questions that make them feel like they’re in control. Your prospect has to decide to move forward on their own by giving them a vision. Position yourself as the person with the solution.

  1. You’re always safe when you’re in the other person’s world.

You’re safe as long as you’re in their world talking about their problems.

  1. Principle overrides tactic.

Ben’s selling insights:

  1. Dating is the same as selling.

Inviting someone into your world versus coaxing someone to go into your world

  1. The math is on your side.

If you believe you have a high quality product, remember that there is less supply of you than there are of people who need it. So you don’t need to sell to everybody to make a very good living. Then you don’t have to do all this desperate “needy” stuff. What do you care if they reject you? You haven’t lost them, they’ve lost you.

  1. Repulsion marketing

It means focusing on people you don’t want away to attract the people you want by default. The people you didn’t want to buy the product sometimes change the way they think to qualify themselves to have that product.

2 Common mistakes people make when it comes to emailing:

1.Constantly giving free information without selling

2.Pummeling people with blatant sales pitches

Effective emailing strategies:

Mix content with promotion in every email.

Before you send an email, ask yourself: Does this warrant me interrupting their day for a few minutes? If not, don’t send it.

Not letting people know something exists for a sale is selfish because people in your email list are there because they have a problem.

Ben’s Major Takeaway:

You’re always safe when you’re in the other person’s world. Find out what’s going on with them mentally and what the problem is and how they feel about it. Get them thinking about it. Build a vision first then they’ll be begging you to show them a solution.

Episode Resources:

Connect with Ben through Opt in to his list and get the first issue of his $97/month Email Players newsletter.

Jim Camp’s book Start with No

Jim Camp’s interview with Michael Senoff

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Dave, Donald Kelly, The Sales Evangelist, Best Sales Podcast

TSE 369: Sales From The Street-“Ask The Right Questions”

Dave, Donald Kelly, The Sales Evangelist, Best Sales Podcast Asking questions is an integral piece of sales in order for you to uncover your prospect’s true challenges. But how much of your time do you actually spend on developing questions that will allow you to move forward along your sales process? We have an interesting topic on today’s Sales from the Street as Dave Specht shares with us value-packed insights on the power of asking great questions.

Dave is an entrepreneur, author, speaker, and creator of some awesome mobile applications such as Inspired Questions for Family, Inspired Questions for Farmers, and Inspired Questions for Family Business..

Dave is also the Founder of Advising Generations, a consulting practice that works with multi-generational family businesses looking to transition their ownership and management to the next generation.

Here are the highlights of my conversation with Dave:

Dave Specht, Donald Kelly, The Sales Evangelist Podcast


Dave’s biggest challenges:

  • Thinking highly of himself and telling clients what to do
  • People didn’t want to be told what to do

Strategies Dave employed to overcome this challenge:

  • Developing questions
  • Focus on questions instead of having all the answers and being the smartest guy in the room
  • Focus more on providing the right questions so you can get to the heart of what their challenge really is

How to develop questions:

  1. Identify pain points and challenging spots.
  2. Start going backwards and develop questions to help them solve those problems.

What are the questions that can unlock this person to be able to allow them to move forward for their benefit?

  1. Questions have to be genuine to help them figure out and clarify what’s important to them. You become their ally and resource beyond the product you sell then you get the opportunity to implement the solution.

Dave’s Major Takeaway:

Spend an equal amount of time working on and writing down questions as you do learning and understanding your own product.

Episode Resources:

Connect with Dave Specht through email at or go to to check out the mobile apps he created with all different sets of inspired questions.

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The Sales Evangelist, Donald Kelly, Donald C. Kelly

TSE 065: Learn Why Human Relationships Are At A Premium Today!

TSE 65 Jeb BlountDuring this episode I had the great opportunity of interviewing Jeb Blount, Mr. Sales Gravy himself. Jeb founded in 2006 as a portal for all things sales. Over the next five years he and his dedicated team of sales professionals grew Sales Gravy into the most visited sales employment website on the planet. Thousands of employers connect with hundreds of thousands of top sales professionals.  

Today Jeb is a highly sought after speaker and corporate consultant. He is known for  his ability to inspire his audiences to action and keep them on the edge of their seats.

Jeb is also an author; having written five books including his bestseller People Buy You: The Real Secret to What Matters Most in Business and his newest release People Follow You: The Real Secret to What Matters Most in Leadership.   

Jeb has a passion for growing people and the unique ability to see potential in everyone. Over the span of his career he has coached, trained, and developed hundreds of Sales Professionals, managers and leaders.

Here are some of the major takeaways from our discussion: 

  • The way we sell has not changed, but the tools that we have to interact with each other has evolved. The sales process may be different, but we are still applying the basic things of finding pain and providing a solution for the buyer.
  • Listen to your clients and don’t try to “pitch them”. If you listen to your clients, they will teach you how to sell to them.
  • Pitching your product will make you look like everyone else.
  • People will buy on emotions and then justify later with logics.
  • “The most insatiable human need, is the need to feel important”.
  • Have a list of Go-To-Questions that you can fall back on. Practice them over and over again so that they become internalized and become apart of you.
  • Focus on what is most important to the buyer. Remember, “People Buy You”!

Jeb’s Books:

“People Buy You”

Stay In Contact



Twitter: @Salesgravy


Jeb’s Podcast: SalesGravy