What AI in Sales Really Means


As we continue to hear about the values of AI in sales it seems to me that people are missing the bigger picture. This post is designed to help us start to address this. It will cover everything from AI vs Generative AI, AI in Sales Interviewing, using AI for Better EQ in the Sales Role, AI in Prospecting, AI in the Sales Funnel and Sales Process, AI in Sales Demos, AI in Sales Negotiations, AI in Revenue and Sales Operations, AI in Territory and Account Planning/Account Mapping. 

This is being written to help those of us in the sales community start to connect all the dots. It is not meant to be the final picture. And of course, this is simply my interpretation. I am more than happy for someone to call me out and tell me what I got wrong or misunderstand in my current mindset. 

Before we dive in, let’s make sure folks understand the difference between AI and Generative AI. I am a layperson so if someone wants to correct me, please do.

To the best of my knowledge:

  • AI is often thought of as the ability to recognize patterns and make predictions. 
  • Generative AI is often categorized as the ability to create new content in the form of images, text, audio, etc. 

So, using these definitions, one example of using AI in sales would be along the lines of recognizing patterns in various parts of the sales funnel. Easiest reference is probably in outbound prospecting as we look to get data around best subject lines, best value props, best open rates, and best response rates in relation to data.

Now, if we think about Generative AI, then we are taking this one step further. Well actually, several steps. The first step might be to take the data gathered and have the tool come up with even better content. And on top of that, it’s possible to use other sources around personality profiling to create best practices for prospecting based on your ICP (Ideal Company Profile) and your IPP (Ideal Persona Profile) 

I am sure there is more to this and for now I think it’s a good foundation for the rest of the commentary. 

By the end, I will give you the one secret that I think ties all of this together and will make our jobs that much easier and make it more enjoyable to utilize AI and Generative AI in sales. 

So let’s begin.

Better EQ 

It is actually going to help with teaching everyone from the revenue team from ops to CROs, VPs of Sales, sales reps, and SDRs with their EQ. 

Yup, AI in Sales is going to actually make you smarter and better equipped over time. 

Everything from better interviewing to using AI in sales is further down the funnel. Meaning demo conversations, pricing conversations, improving negotiation skills. 

Interviewing Research

So you’re a sales rep going into your first interview with a VP of Sales and you want to do your research:

  1. You research the company.
  2. You research the person. 
  3. Maybe you have a personality tool that gives you insight into the person’s personality. 

These are all great and things we do and yet sometimes we have a hard time connecting the dots. What if you went into your favorite AI tool and asked it write a biography on this VP of Sales you will be interviewing with?

  • What if you went and asked your favorite AI tool to write a summary of the personality of the VP of Sales? How would you use that in the sales interview?
  • What if you use AI to better understand their personality to things, such a preference to bullet points or storytelling?
  • To know if they prefer to be direct, or walk through things?
  • To know if they make decisions quickly or prefer taking their time?

How would you adjust yourself in the sales interview?

Now, say you have a group interview. What if you did the same thing for each person you were interviewing with?

Now say you are required to give a presentation as part of the interview process in front of a group of people. 

Wouldn’t it be good to build your presentation with bullet points on a slide and then have a story to tell while on that slide to get through to all those attending?

And finally, what if you do this for several interviews at different companies. Would your EQ in general become better? Would your skills for listening, observing, and communication become better? Not just in the business world, but in real life too?

AI in The Sales Funnel, Sales Process, and Revenue Operations 

Whether you call it Sales Operations or Revenue Operations, Generative AI is going to make your job so much better and make you that much smarter. 

If your fear is it will replace you, you are probably right. And you have two options. One, bury your head in the sand and pretend like it won’t happen, or two, embrace what is happening, dive in deep, and figure out how to better use technology to your advantage. 

Maybe you become the best at implementing generative AI in the sales process. Someone is always going to want to hire you. Maybe you become so good you start your own consulting business and stop making everyone else a millionaire and start making yourself one. 

I digress…

Where I see Generative AI supporting the Sales Ops and Rev Ops roles is to better examine the data collective at a higher and holistic level and then make the recommendations for change. 

Remember, we now have access to all kinds of data.


First and last name, geography, education, personality insights, gender, race, age, tenure, role, language and conversational insights, etc. (Note: I am not a fan of the gender and race portion for ethical reasons. However, we cannot pretend this is not something that could be captured and utilized. Ethically, I would not want to do that or associate myself there. Simply saying what others have probably thought.)

Professional :

Education, titles, roles, tenure, verticals, sales cycles, deal size, company, company cultures,  to whom they report, who reports to them, and so on.

Yeah, I agree, this is some scary sh*t.

And we cannot ignore it. 

Now back to AI in Rev Ops and Sales Ops. With all this data around our messaging and value props, along with their personality and professional insights, and specifically data around our sales cycles, Generative AI may be able to better clarify the following:

  1. Proper Sales Staging
  2. Proper Exit Criteria for Each Stage
  3. Better Expectations around time in Stage
  4. Better answers to “What is the one thing preventing this deal from closing?”

And when you put all this together, Generative AI should be able to help us better craft our messages to the personas we are speaking at the right time. And when this happens there will be fewer bad deals in the pipeline, improved forecasting and improved closing. 

Now from an Ops perspective, you are the one who is running this machine and taking this information and sharing it appropriately throughout the org. 

EVERYONE will want to see this information for many reasons, and in some cases the reasons are cross-functional. 

  • C-Suite – Wants the forecast and revenue, why deals are getting lost, why deals are being won.
  • VP of Sales – Wants the forecast, revenue, and individual performance.
  • Director of Sales/Sales Manager – Forecast, closing ratios, individual performance. 
  • Sales Reps/SDRs and BDRs – Performance to goal, and then what they can do to improve. 
  • Customer Success – How are all current customers using the product and what is the right and next service or product to recommend based on their usage, vertical, similar companies, etc. 
  • Sales Enablement – What do we need to be teaching the team specifically to help them improve?
  • Product Development – What are the customers and prospects saying about the product or service?
  • Marketing – Messaging resonation.
  • Dev Team – Similar to product development.
  • HR – Based on performance HR, this could look for better candidates for interviewing. This actual use case is probably relevant for every other title mentioned here as well. 

Now, can Generative AI provide all this insight to the right people in the right teams in your organization without you? Probably, above my pay grade. My hope is, maybe, and it will actually still take some human element to help break this down. At least for now. 

And so, as I mentioned before, this is what I think you need to embrace if you are looking to understand how Generative AI is going to affect your Sales Operations or Revenue Operations role. 

Could you get replaced? Sure. Remember, especially in the start-up ecosystem, AI and Generative AI in sales is just getting started. Someone needs to be an expert, why not you? Embracing AI in your Ops role will allow you to have the most knowledge of how to execute a Gernative AI solution with best practices. You become the most sought after skill for the next 5 years, at minimum.

AI in Sales Prospecting

AI during prospecting in sales is pretty much table stakes at this point. If you’re company is not doing this, well, it’s time to find a new company. 

Of course, your SDRs and BDRs should be using AI in prospecting. 

Now, what about your AE’s? The good AE’s are already doing it. As for the “Grumpy Gus” sales people who think prospecting is beneath them, well now they have nothing to complain about. 

The message is written for them. 

The email is written for them.

The voicemail is written for them.

And if they don’t get on board, they can use AI to write their resignation letter or you can use it to write the severance agreement. Yeah, don’t be surprised, I’ve seen some people do this actually. 

AI is Sales Qualification and Discovery 

So imagine this. You are going into a sales qualification or discovery call with someone you have never met. You have done the basic research of the organizaiton, them as an individual, and if wise, perhaps who you think they report to. 

Then you go and pull the AI information on personality traits, how they like to receive and interpret information, how they like to make decisions. 

  1. If they prefer to read something, do you send something before the meeting?
  2. If they prefer to hear something, do you make sure you have the right story?
  3. If they prefer to use data and evidence to make decisions, you use that properly?

And perhaps AI can even tell you the best way to ask these questions. And better yet, exactly how to say it based on their personality. 

This is what AI in Sales really means. 

AI is Sales Demos

So imagine this. You had your first sales call and now your champion has gotten you a demo with key stakeholders. In attendance will be a C-Level Exec, a VP or Director, a manager, and an end user. 

Just like the interview example. You do your research and now you have personality traits for all the attendees. You can now do the following:

  1. Build a better presentation/demo.
  2. Know which things may matter more to the different people.
  3. Know how each person likes to absorb information: Bullet Points, Stories, Seeing It, Hearing It, Touching It.

Now, over time, with many conversations does your EQ improve your sales skills? Does your EQ improve your life skills. 

Yes, there are probably some more structured sales training and EQ training available and those should definitely be explored. And as we say in sales training, we need more role-playing, more at-bats, using AI in sales in such a way does this, and there is no better experience than the real-world. 

AI in Pricing and Negotiations

Now imagine, you have to deliver pricing to your champion. 

Yes, do your research and figure out how to present for them to absorb and understand. 

AND… then do your research to understand how their boss, and the head of their finance department likes to see, hear, and absorb information.  

Now, when you deliver pricing, you can build it in such a way that could give you a leg up. In fact, if you share this knowledge with your champion and explain to them what you know, and get them to tell you if it’s correct about the other people in the buying committee, you just made their job that much easier. You just helped to get them to “fall-in-trust” with you. They will not see you simply as a sales person. They could now start to see you as a true ally and someone they want to do business with.  

AI in Territory and Account Planning

Let’s face it. Territory planning and account planning is an old-school, manual, and essentially a guessing game process. We look for facts that we want to believe are true, and then justify and rationalize them to be true. When in fact they are just guesses. Then, SURPRISE, when they are wrong, executive leadership wants to get angry at us. 

Now for those selling into the Enterprise space here is what AI should be able to help with if not now, then very soon. And for enterprise sales I am defining this as 12-18 month sales cycles, $250,000+ deal sizes, etc.

Your company requires you to build a plan and/ or an account plan. 

  1. What if AI can help you determine which companies in your patch are most likely to be looking for a solution such as yours?
  2. What if AI can help you determine which companies most likely will have budget for a solution like yours?
  3. What if AI can help you determine which companies are the early adopters of technology and most likely to be open to your solution?

How could you better use this information for your Sales Territory and Sales Account Planning Strategies?

What Everyone is Getting Wrong About AI in Sales

So, as you can see, AI and in particular, Generative AI in Sales, is not really about prospecting. It’s about a whole lot more. It will touch every part of the sales cycle and sales funnel. It will touch every part of the organization from marketing to IT, and to HR. 

So here’s the big secret I mentioned at the beginning. 

One of the biggest mistakes I see in sales is the lack of sales training and coaching around Pre-Sales Preparation. Everyone claims to do this, and everyone wants to do it. And yet, 99.9% of the time when I ask someone to show me their pre-call planning worksheet, nobody has one. You can get my template here along with a sales process creation document.

Imagine this, you just set a meeting for next week with your champion and 3 additional stakeholders. Their emails are in the calendar invite. 

And then, within 15 seconds you have an email sent to your inbox:

Subject Line: Pre-Call Prep for Meeting XXX Company.

Paragraph 1 – The Hard Data 

Basic bio of each person who will be in attendance, name, title, tenure, education, geography, etc.

Paragraph 2 – The Company Culture: 

This is the stuff mentioned above about their internal culture, probability of needing the solution, are they early adopters or laggards generally, financial health. And perhaps, even something around who will be the decision makers and who will be the skeptics in the decision making process.

Paragraph 3 – The Soft Skills Data: 

Specifically, how they like to absorb information, visual, auditorily, and kinesthetically. AND it includes the specific language and words (yes, a script) that will resonate with each personality. 

Paragraph 4 – The Objections: 

Yes, I want a list of the objections I should expect overall, and based on the people attending the meeting. I then want to know exactly how to address these based on the person who is most likely to ask them, and finally, I want the exact words and phrases. 

A +1 to this would be to know when, where, and how to bring these up in the conversation BEFORE the prospect brings them up.

Paragraph 4 – Power Point(s): 

First, I want all of this also in a PowerPoint for me to easily digest and make it easier to share with my team internally. And if I need to present a PowerPoint, I want the PowerPoint created based on the personas of the people who will be in attendance, including all the notes and little stories for each slide of the presentation. 

Paragraph 5 – The Demo: 

Just like the PowerPoint, I want the system to give me the outline and flow of a demo based on attendees, expected objections and where they would occur, what to say based on this, and, of course, what things to probably avoid. 

Oh, and one more thing.

Let me conclude by explaining why I love AI and Generative AI in sales. Assuming we can get that email from a system. And assuming over 6 months I use it regularly, what happens to my Sales EQ? What happens to my life EQ? I am willing to bet, as mentioned before, this is what will improve our sales skills, and yes, continue to make us invaluable. 

And sadly, there will be the one thing, the “Yeah But-ers”.

The one thing will be the people who will claim they are smarter than the machine. You know the ones, they are the ones who say, “Yeah, but there was this one time when I was right and the machine was wrong.” Those folks are going to be weeded out very quickly. 

Another way to recognize the “Yeah But-ers” is simple. They are the ones who take the personality tests and say, “Oh yeah, that’s me, that’s me, they nailed me there. AND then they say, but they got all this other stuff wrong.” Please stop that silliness. 

So, what do you think, are you onboard with AI in sales or you going to be an ostrich?

Oh, and to all you AI in sales companies who use this to build your product roadmap, you owe me $$$, my venmo is rh415.

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