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AI has changed how companies prospect, research, and communicate, but many of the world's largest technology companies continue investing heavily in human sales teams. This episode explores what AI can automate, what it still struggles to do, and why trust, judgment, and complex buying decisions continue to require skilled people.
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Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.
About Ray:
→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.
→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.
→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com
→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.
→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com
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I just told 60 SDRs and 50 MSP owners that AI is the absolute best thing that has happened to good salespeople, and possibly the worst thing that's ever happened to mediocre salespeople.
About half the room thought I was crazy initially. By the end of this talk, nobody did because the data that I'm about to show you is the opposite of what you're hearing online about what is happening in AI today, particularly as it relates to sales.
It has massive implications for anybody who's in sales today and wants to be, or is expecting to be, in sales tomorrow. Here's that talk.
So my team told me I had an opportunity to talk to the entire group, and I'm really excited to do that. I went through a bunch of topics that we could cover, things from objection handling to scripting—like tactical sales stuff.
And I decided to talk about something far more controversial: how AI is affecting your role today as an SDR. So, today what we're going to do is we're going to zoom out for a minute and we're going to talk about what's real in AI today, what the future looks like for you guys, and how to future-proof yourself and your role in sales going forward.
We'll start high-level, and then by the end of this, you're going to walk out with five specific things that you can do to leverage AI in your favor today.
Real quickly, I know most of you know me from MSP Sales Partner, so I'll be really brief here. Suffice it to say, I've managed a billion dollars in sales over the course of 25 years.
I've led turnarounds for eight sales teams in my life. I've led national sales for the US Chamber of Commerce. I've led turnarounds for private equity companies as a CEO, and I've led sales for Robin Robins internally, who is, as you know, the top MSP marketing influencer in the world.
I have been an expert-in-residence at TMT for over seven years, and I've led sales at other groups for people like Dan Martell and other names that you may know.
All of my experience has given me a little bit of a contrarian opinion on AI in sales today—at least as it relates to everything that you're hearing online.
I've been through a lot of transitions. This is age speaking now. I've been through "Caller ID is going to kill cold calling." I've been through "Automated answering is going to kill cold calling." I've been through "Email is going to kill cold calling," cell phones, texts, do-not-call lists. You name it, I've seen it.
I do think that there is something different about this particular transition, though. The biggest difference is I actually think it's the opposite. I think AI is the single best thing to happen to good salespeople, or SDRs specifically, since the inception of the role. I genuinely mean this; it is true to my absolute core.
I know a lot of you are thinking, "Well, hey, I've seen on LinkedIn that the SDR role is going bye-bye, the BDR role is going to disappear. We've got Claude replacing everyone who's doing cold outreach, so the inside sales role, the prospecting role—that role is dead."
Maybe you've heard someone at another company talk about, "You know, we've replaced our entire SDR team with AI," and maybe you've seen the demos of people on social media that show their little 30-second TikTok video of full calendars, watching Claude fill everything up with the push of a button.
It may be making you wonder, "Is this role today—the SDR role, or sales in general—is all this stuff going to be obsolete soon?"
What's actually happening out there? We work with a lot of companies in the MSP space, the AI space, the SaaS space. I own MSP Sales Partners; we work with hundreds of MSPs specifically. I speak at all the events, and I have a large network, so I get exposure to the entire pipeline, activities, everything. I see under the hood.
I know that a lot of what you're hearing online is misinformation. I know it. When you peel back almost every one of these "Hey, AI replaced our SDR team" stories on LinkedIn, you usually find one of three things.
One is you've got companies who are masking layoffs. The company was losing money, they needed to cut head count, and you know what? It sounds a lot better to say "AI productivity" to your board members, your investors, and to social media.
That sounds better in a press release than "We couldn't afford our team anymore." Hey, we can lay off people and actually make it look like we're doing great and doing smart things. Okay, well, that is happening behind a lot of these stories.
The second thing that we see happening is that the SDR team that they supposedly replaced wasn't producing shit to begin with.
Right? Because building the SDR function, the BDR function—cold outbound—that's hard. You know this. You're doing the job every single day; you know how hard this job is. I know how hard it is to build this function as a business owner, as a sales manager.
You've got to have good processes, good coaching, and all of these things in place if you want real pipeline. In most of these "We replaced our SDR team" cases, they never had that to begin with, and you can't replace a pipeline that never existed. So, this is happening: "We're replacing our SDR team with AI," and it will be yet another flop, yet another thing that we said we were going to do and didn't get any actual results from.
And then the third thing is they bought into the hype. They got really overzealous with this. They installed a bunch of AI, bet on it heavily—too heavily—and it didn't work. They're going to be quietly rehiring humans in the next 12 months when their pipeline collapses.
The best example of this is actually Salesforce last year in September. Their CEO cut 4,000 customer support roles, and he said—the quotes, the headlines—"I need less heads." They had Agentforce AI, and that was going to be doing all the work.
This is a company that invested heavily; they are AI, right? That was the headline. Front page. Six months later, they're hiring 2,000 people back. They're hiring sales reps, they're hiring a thousand new grads, and the CEO now says, "Blaming AI for layoffs is a lazy way out and a scapegoat. We're hiring." You can see the quote.
Okay, well, if Salesforce—the company that builds and sells AI sales agents—if they can't run their own business, their own Salesforce, and their own sales team with AI agents, what does that tell you?
So, when you hear "AI is going to be replacing SDRs, AI is going to be replacing salespeople," you've got to filter that feedback, you've got to filter that message through those three buckets, okay? Because that's usually the real story.
By the way, Amazon had this same problem. You can look it up. Amazon operationally ran into the same thing: they over-bet on AI, got overzealous, and then it started deleting entire databases, caused millions and millions of dollars of damage, and millions of missed orders. This isn't just a one-off outlier claim.
AI is going to affect some SDRs; I'm not saying it's not. I'm not going to pretend that. The bottom 50% of this profession—those SDRs are going to be in real trouble. AI does mediocre stuff better—very repetitive stuff better. It does it better than humans, more efficiently, and the math doesn't lie on that.
But the other half—the top 50%—those SDRs, you on this call, if you are here and getting this support, investing into these programs, and doing what you are doing right now—if you can write a real email, ask good questions, hold a real conversation, and ask good discovery questions, you are about to be more valuable than you have ever been before when it comes to this particular role.
Here's the good news: anyone on this call can be a top 50% SDR. I know the math says only 50%, but anyone on this call can make it into that because there's no magic about it. There's no IQ test, no prerequisite, no specific thing that you have to jump through. It's basically just acquiring specific skills. It's a skill stack—combining multiple skills of the role, several of which weren't relevant to the role years ago or even a year ago.
But it's very much the same way a mechanic—a top 50% mechanic—is a skill stack. They know how to do multiple things and combine those efforts into a stack that makes them more valuable. A nurse does the same thing; they have multiple skills, a skill stack, and you learn it, you practice it, and that's how you get there.
So this role that you guys are in, it's not dying. The bottom 50% of this role—which I'll break down in a minute—maybe fading in value. And it is, frankly; I don't even need to hedge that. But the top 50% is about to be the best paid and the most leveraged entry point into sales than anything else out there.
I'm going to show you proof that this role isn't going anywhere. I'm going to show you the trap that puts a lot of SDRs into the bottom 50%, and I'm going to give you five skills that I would leverage if I were in your shoes today, plus a specific plan to learn each one that puts you in the top 50%. Alright, now let's get into that.
Part one of four here: I want to start with a single piece of evidence that none of the AI sales hype bros on social media are talking about.
The companies that know AI better than anyone else on the planet—the companies who are actually building it, the core companies that are actually building it with all of the talent, hundreds of millions and billions of dollars being invested in the talent at these companies—are hiring SDRs in droves.
And not just hiring, they're building entire SDR functions from scratch now. Right now, these companies are hiring. In fact, there's a number—we did a little bit of research on this—39% of the top 200 AI companies with go-to-market roles right now are hiring SDRs or SDR leaders. That's PeerSignals' AI index published just a couple of months ago.
Let me show you what this actually looks like. Anthropic, the company that's building Claude—obviously a ton of talent, a ton of AI knowledge, so they know how to engineer AI, I would say—they're hiring BDRs in San Francisco, they're hiring BDRs in New York, they're hiring BDRs in Europe.
And the job description says explicitly: "Outbound against strategic prospects to generate high-intent opportunities." It's what you do. This is your job, and they're hiring right now.
OpenAI, the company that made ChatGPT, they're hiring SDRs in San Francisco and Dublin right now. They're hiring a head of sales development to run the SDR teams and build their first enterprise SDR function—from organization from the ground up.
I think their OTE was roughly like 140 to 160 plus equity for US-based roles. $140,000 to $160,000 plus equity for US-based SDR roles. Let that sit in.
Here's another one: ElevenLabs, which is the voice AI company. This is the company that makes the technology that you would theoretically use to replace the caller. They know voice AI better than anybody on the planet; they're the leader in the space. They know how to do this, and they have SDR roles open in the US right now at $180,000 a year.
The voice AI company is paying humans 180 grand to pick up the phone. Sit with that for a second. Anthropic, OpenAI, ElevenLabs, Clay, LangChain, CoreWeave, Harvey, Sierra, Cursor—every hot AI company you can name right now is building human SDR teams. If anyone was going to replace SDRs with AI, it's going to be these companies, and they're not. They're voting with their checkbooks, and their checkbooks say, "We want humans, and we want a human picking up a damn phone to talk to other humans."
What about the stories that you may have heard about companies that have replaced their entire sales teams with AI agents? Okay, let's talk about them. Some of them are true. There are companies today that have successfully replaced humans with AI functions for certain types of selling. I want you to understand exactly what we're talking about here when you hear this.
Imagine a sale where a buyer is looking up stuff. They already know the brand, they've Googled it, they've come to the website, they fill out a form, maybe they even know the price range, and they want to confirm the price, know when they can get it, and know how to pay.
Alright, well, that's an order-taker job. It's inbound, it's transactional, it's high-end customer service with a credit card swipe at the end. An AI agent can do that pretty well because you can build a chatbot that can pull up the pricing, grab an FAQ, and book a full demo or something without a human being in the loop. Honestly, it probably should; that's good customer service, it's efficient.
But that's not what you do. I wish it was that easy for you. You're picking up the phone, you're calling a business owner who's never heard of your company, you're interrupting their day, and you're trying to convince them to give you 15 minutes. You're trying to capture attention in 10 seconds, and then you've got to respond on the fly, ask the right discovery questions, and try to introduce a service they definitely weren't thinking about right now and may not even know that they need.
Like IT services—definitely not what somebody's thinking about most of the time in their day when you call them. That's a completely different sale, and AI hasn't cracked that—not even close. And it won't for a significant period of time.
Now here's the proof, and this doesn't get talked about very much, but 11x.ai was one of the loudest "We replaced cold calling SDRs with AI" companies. Right? They put logos like ZoomInfo, they put logos from AirTable, and they put them as success stories on their website.
TechCrunch went and checked it out, and guess what? They weren't customers. Not only not customers, they were failed pilots. They did trials—these companies did trials—and they failed. And these companies said, "No thanks, moved on." And 11x.ai actually just kept lying, right? They were caught publicly lying about who was using their actual product.
So the whole "AI is replacing cold call SDRs" narrative has been at least partially built on things that we know are fake case studies—people trying to sell you AI shit.
What does conversion with AI look like versus human outreach? Well, at the very top of the funnel, AI looks like a winner. The reply rate is a lot higher. Okay, that's pretty significant—three times higher for AI reply rates. That's the number a lot of vendors are putting on their slides like, "Hey, 3x your response rates." Okay.
But what happens as you move down the funnel towards an actual signed deal? That's what we actually care about. Do you want appointments? Do you want sad appointments? Do you want discovery calls? No, you want signed deals.
Lead-to-meeting: humans convert at about 21%, AI at 8%—almost a complete flip. Meeting to real opportunity: humans about 25%, AI about 15%. And by the time you reach a closed deal—so an AE or an outside sales rep—the win rates on AI-sourced deals run 9 to 12 points below human-sourced deals.
So, AI is better at getting a click, and humans are actually better at getting customers, which is why we're in business.
Now here's the other issue that happens from this: all of that noise that comes from having three times the number of people respond at the top of the funnel, that's got to be handled. It's not all handled by AI; it creates more noise, creates more chaos, more shit is happening, more garbage data—all of that—as none of it goes through, and fewer deals result.
The gap doesn't shrink as you go down the funnel; it widens. The closer you get to actual sales, the gap gets wider. So, AI is better at getting a click, and humans actually get the deals.
Usually when I share that, what I hear is, "Well, that's AI only. So yes, maybe the conversion is significantly lower, okay, but there's no employees, no payroll, it can run 24/7, it's going to get smarter, it's going to get better, it's going to catch up with humans in no time." Okay, maybe it sounds like a good argument. It's just not what's actually happening from the sales leaders and those of us in the trenches.
Let me show you the curve that we keep seeing, and we've got some data on this too. Month one looks like a win. You get some initial responses, you get some traffic, you get excited. Okay, cool. Month two, spam complaints creep up. AI is driving this volume because it's got to win on volume if it's going to win. It's got to win on volume. We know the conversion rates—like even the personalization and all that shit—it's not nearly as relevant as a human doing this.
So, spam complaints start to pick up, inbox placement starts to slip, and because AI is firing out four, five, six, seven times the volume from the same infrastructure, the inbox providers—like the email providers—start to notice.
Month three, the inbox placement falls below 60%, the meetings dry up—basically zero—and the domain is torched.
One CRO I read about had really great numbers for two months and then literally zero by month three after spending 50 grand. For anyone doing outbound, this is the part that should be a flag or concerning: when AI burns your domains, it doesn't just kill the robot's emails; it takes all your humans down with it.
So the impact is widespread. Your sender reputation plunges, and every email that your company sends—including the ones that your reps send by hand, often times the ones to your actual customers—starts to land in spam.
47%—nearly half—of deployments from AI outbound hit walls within 90 days. So nearly half got their domain torched. 21% didn't recover. Think about these AI deployments: you go out, you put your hard-earned reputation at risk, your domain gets torched, and 21% never recover from that. It's a torched asset; there is a real cost to that. That's why 50% to 70% of these tools get ripped out after 90 days. The market's already run this experiment; it's not cheaper, it's not catching up, it has this cliff, and it poisons the well for the humans that are also trying to do the outreach. There's another number that I saw from MIT that said 95% of AI pilots are failing across small and big companies. Well, this is explaining what's happening—just one version of it.
So here's what's actually winning, and I want you to notice that you are at the center of this, okay? So, what's actually winning? The human being the engine and AI being the multiplier.
If you look at pipeline generated per seat per month, AI alone—no human—produces about $94,000. Call that 1x; let's just say that's our baseline. A human: about $187,000, so double. 2x the returns of what AI does by itself, and that's the human—no AI bundled on or any of that—doubles the machine, the robot results.
Now, you give that same human AI leverage—researching, drafting for preparation, for follow-up—$278,000. That's 3x. We've got sources on this; we've aggregated some studies, we dove deep because I know first-hand what's happening. I'm seeing it with my entire network of sales leaders who are seeing and saying the exact same thing. So we dug into this and we said, "Damn, what we're hearing and what we're seeing and what we're reading doesn't seem to align with what's actually happening." And this is it; we pulled the data.
Here's the part that I really want you to hear: take the human out and you fall all the way back to 1x. The leverage multiplies the human; it doesn't replace them. You are the thing being multiplied. Your output, your value is being multiplied.
Since all of you on this call are calling in the US, there's also this legal moat that people don't talk about. The FCC said about a year ago, a year and a half ago, that AI-generated voice falls under TCPA—the regulations. Which means you need prior written consent before you can call a US prospect with an AI voice.
If you fail, if you don't do that, it's $500 per call in statutory damages. $1,500 if it's willful. So, $500 if you're like, "Hey, we blitzed, we didn't know, sorry." $1,500 if it's willful. Now think about that: you're using AI to push volume, that's a lot of money that you are putting yourself at risk for if you were doing this the wrong way.
So, the AI cold calling dystopia that everybody is afraid of just—it's not just unproven, it's actually illegal in a lot of markets. This is what the reality is right now.
There's a fork in the road right here because, like I said, AI is affecting things. As we showed on the other chart, 3x the results—that's pretty kick-ass. So there are changes that are happening that are leading to that, and I will say I think there's two SDRs that are going to walk out of this room. Same starting point, by the way, same starting line. You're going to end up in two completely different places in 12 to 24 months. That part I also believe, and that's why I say it is the best thing to happen to good SDRs and it is the worst thing to happen to people that do not do what they need to do to get into the half that's leading the charge.
So, SDR 1 hears everything that I say and does nothing with it. Okay, like you've heard all this, you see the numbers, you're like, "Alright, I'm safe," and you treat the role like it's a fixed script—like things are going to stay the same. What happens to you if you're in that space is you're going to see the role is going to get harder. The market is going to get filled with AI slop because, despite what the numbers say, there's going to be more and more people that are saying, "Hey, I'm going to try it, I'm going to try it." So the market gets buried in more AI garbage.
Response rates start sliding more aggressively, and the old way of doing this job fades in importance. That SDR doesn't get replaced by AI, by the way; that SDR gets replaced by another SDR sitting next to them who decided to adapt.
That is SDR 2. SDR 2 hears this same thing and takes this as a challenge to like, not "How do I survive this?" but "How do I lead this? How do I take part in this? They're hiring SDRs for 180 grand at AI companies? Well, shit man, count me in. I want to be part of that party."
And so they become the most AI-leveraged person on their team—smarter, faster, more targeted. They, you, stop waiting for opportunities to get handed to you. You start bringing opportunities to the table. You start bringing new opportunities to the role—new plays, new angles, new ideas that maybe your manager hasn't even thought of yet. Same job title, same phone, same starting line, and one fades with the old version of the role and the other leads the charge into the new version of it.
That person becomes the most valuable person on the team doing it because this is hard work. Creating new opportunities is hard work. The AI companies and those leading the charge know that, and that's why a leveraged SDR who is augmented and amplified by AI—not afraid of it replacing them, but embraces it and leverages the shit out of it—is now 2xing and 3xing what that same role was getting paid before.
Here's what I ask you to do today: commit to upskilling, not someday, but this week. Because this role is not being replaced by AI; it's being rebuilt by the people who lead with it. The only question is, which of those two SDRs are you going to be?
It's not replacing the role; it's replacing a lot of the boring stuff that you don't want to do anyway. So embrace that part of it, let AI do that, learn how to use AI to do that, and take the portion of the role that is left and leverage the shit out of it.
The five skills: so what I'm going to do now, if you're with me at this point and you believe that and you understand that, what I'm going to do is give you five skills, and these are the skills that determine which side of this fork you're going to end up on—which of the two SDRs you're going to be.
The way that I thought about this was, if I were you on this call, what are the five things that I would upskill on? What are the areas that I would focus so that I can ride this wave instead of getting hammered by it?
The best news is you can use the technology that a lot of you are actually afraid of replacing you—you can use the same technology to future-proof yourself from that technology if you do it, if you leverage it. You can use the tools instead of letting the tools use you. These are five skills that I think are the most valuable for you going into the future.
What I'm going to do for each one is I'm going to give you two prompts. The first prompt is the "Today Prompt," and that's to get AI to help you do work tomorrow morning—like real, applied, useful right away, quick win.
The second prompt is a "Teacher Prompt," and I think this is the really powerful one. This is what turns AI into your personal coach to actually learn a skill over the course of 30 days, using free resources, things that are publicly available, and the tool itself, and learn it from the best practitioners in the world.
I'll be honest with you about something: if you just take the today prompts and you start copy-pasting it and you call it a day, it'll help for a minute, but that's not upskilling. You're just borrowing AI's judgment. The teacher prompts are the real game, so I recommend both.
By the way, I'm not going to read every single prompt to you, but I'm going to give you a quick overview, and then to get access to it, I'll tell you exactly how to get all these prompts so you can copy-paste them if you want.
Before we get into any of this, what I will say is you want to add context to these prompts. Make them better, use these as inspiration, use these as a foundation or starting point. One thing that you want to do—which we'll talk about in a second—is add the right context. The quality of the input with AI determines the quality of the output.
So, the better context that you provide on the front end, the better and higher quality and more personalized the output will be on the latter end. So, what I would do is create a prompt like this; you can customize it however you want. Again, this prompt is in—it's at mspsalestoolbox.com—and if you drop in your email, you'll get access to an entire folder of a bunch of resources, actually. But this is one of them, and it should be up at the top. We've got the whole playbook in here for you to use.
So, this is in there; copy and paste it. Basically, what you're saying is, "Hey, I'm an SDR, I work for a managed service provider, this is what I do, this is what my job is, this is what we focus on, and this is what I want—this is how I want you to tailor some of the feedback." So read it, customize it as you want, but this will help give you a better output for the five skills.
So, the first one is Persuasion Copywriting. Every one of you writes copy whether you know it or not. The voicemails that you're leaving are copy. The follow-up emails that you write, that you send—that's copy. The LinkedIn DMs that you're sending, that's copy. The first 10 seconds of your call was copy that maybe we wrote for you, but that's copy. It was on a piece of paper at some point. It was somebody thinking about psychology; it was somebody thinking about persuasion; it was somebody thinking about messaging, about the audience.
I think this is actually more important than ever because, as everyone relies on AI to write their shit, it's going to be a race to the bottom. It's just going to be AI-generated slop everywhere. I mean, you already see it in social media; you're already looking at it going, "Is it real? Is it fake news? Is it AI? Is it this and that?" Well, as everyone does that, those of you that know how to write five lines that can get a 50- or 55-year-old business owner to stop from whatever they're doing in the middle of the day and read, or stop and listen, you become irreplaceable.
That is one of the higher leverage skills on this entire list, period. So, being able to craft a compelling message, get the copy down, and then what you're doing is executing it, is an art and a science, and it is absolutely a skill that you can learn. It's a meta-skill because once you get that, it's applicable everywhere.
I just named a few channels, but all of you are writing copy in one way or another, and the question is: is it AI slop? Is it good? Is it persuasive? Does it convert? Is it clear? Is it concise? Is it jargon? Is it big blocks of text? Is it stuff that's not necessarily readable, doesn't digest, doesn't resonate with me as a prospect? You name it.
So, I've got here basically two prompts. "Hey, you're—" you tell AI, "You're a direct response copywriter who's written a bunch of outbound emails for B2B services. Here's my current follow-up email. Boom, drop it in. And what I want you to do is critique it." So that's all here; you can start using that today, and hopefully that's helpful.
What's more important to me if you want to upskill—if you want to learn the skill of copywriting—and if you want to be the SDR of tomorrow, you have to learn this skill. Go tell AI, and do like a—put this into one of the smarter models, right? So if you're on Claude, it's Opus, or whatever your tool of choice is, but tell it, "Use your smart version and say, build me a 30-day self-paced curriculum to deeply learn direct response copywriting as it relates to cold outbound for B2B services. I want four weekly themes with a clear learning goal for each week, a mix of free resources, specific books, chapters from legendary writers like Ogilvy, Schwartz, Halbert, Kennedy, specific YouTube videos," and it goes on. You can see the rest of the prompt.
But what we're drawing on is we're saying, "Hey, don't just write me copy. I want to learn what good copy is. Once I learn what good copy is, then I have a better idea of whether what AI is giving me is worth a shit or not." Because a lot of times, we take this first prompt and we say, "Hey," and we get the output, and we trust it. How do you know if it's good or not? That's one of the reasons a lot of companies hire us—because they could take call transcripts and put it into ChatGPT and say, "Hey, is this a good call or not?" When they read the feedback, what they don't know is: is that good feedback or not? So, what you want to do is learn the skill—the meta-skill. This builds you a curriculum in 30 days. I promise you, you are a better copywriter, you are better at your messaging, and you will be better on the phone almost immediately.
Second skill is highly targeted, signal-based prospecting. Most of you right now are calling on a list that has been provided to you, which is fine. If somebody handed it to you, loaded it into your CRM, that's fine—not criticizing that. But that list may be the same list that every other MSP in your market is using, too. Anybody can get a subscription to Apollo, anybody can get a subscription to Seamless or ZoomInfo or whatever it is, and that doesn't make it bad; it just makes it busy.
The future of prospecting is signal-based prospecting. It's calling people because they fit a tightly matched target market or ideal client profile (ICP), or you know whatever that vertical, that geography, that whatever it is—it's a tightly defined market. That is how you're going to be prospecting tomorrow.
Or, even better, because something is happening in their business right now that makes your phone call actually relevant. So if they had a ransomware attack hit a competitor, or somebody in the same industry last week, well, shit, make that call. Start calling up everybody in that industry, drop it—that's an interesting hook, 5, 10, 15 seconds into a call. It's relevant, researched; that's how you stand out.
AI isn't doing that shit right now. Maybe they just opened a new location, maybe they lost their IT guy, maybe they're in a regulated industry with a compliance deadline or something that's coming up. And if you know that from AI, you can say, "Okay, there's a compliance deadline coming up." Maybe they posted a job posting for an IT guy—like an IT-savvy office manager. Hmm, okay, maybe they have some IT needs.
So AI can find you a hundred targeted companies to call, and that becomes a targeted, relevant list that you can then customize the messaging for—if, by the way, you know copywriting. You can send AI out to go like scan a couple hundred companies, and in an hour, what you've got is the 20 or 30 that have a reason to take your call today.
As a human, you can't necessarily do that, but as a human plus AI, you can. We've used AI internally; we've used it to generate lists from thin air on very specific criteria. We're like, "Hey, give us a list of MSPs in the US within a specific revenue range with at least one sales or marketing person on staff and an SDR job opening, or an outside sales job opening," or something like that. We've built those lists, and we've watched it get funneled down through the different filters. So, having the ability and the skill to do this on your own is massive for tomorrow and not relying on purchased lists and things like that that come to you.
So I've got two prompts here, same basic thing, I won't go through in detail on these, but one says, "Hey, you're a prospecting researcher. Here's a company I'm about to call, drop it in, get some feedback." It's got some context for MSP prospecting. Stronger prompt, more work, but much, much more impactful: "Build me a 30-day curriculum to really learn signal-based prospecting and trigger events for outbound sales." And then it's going to give you four weekly themes, resources, walk you through how to actually learn how to do this skill. Now another thing you could do is you could add to this prompt and say, "Now teach me how to build this thing within a spreadsheet and make it compatible for XYZ and drop it into the CRM." If you just take this as a mini-course and learn signal-based prospecting, it's going to be a massive source of value for you in the very, very near future—like tomorrow.
Third skill: Cold Calling. Cold calling is the skill that you use more than any other at work anyway. So, it's worth getting really serious about how it works, why it works. Most people, when they start trying to learn cold calling, they immediately jump to all the tactics. They're looking for the perfect opener, looking for the perfect rebuttal, looking for the perfect script. "Give me the perfect script."
The thing is, I can tell you, having been around sales for a really long time, the tactics change quite a bit. What worked two years ago doesn't necessarily work today, and what works today won't necessarily work in two years. But what doesn't change about cold calling or about sales in general is the psychology underneath, because our brains just don't evolve that quickly.
Our buying habits or what we're using for technology might, but our buying habits and how we make decisions as humans, that doesn't really change over a long period of time. Like, why does a pattern interrupt grab people's attention? What is it? How does the brain work? Why do people say, "We're all set" before they've even had a chance to think about it? Why do people do that? Why does trust form or die in the first 10-15 seconds of a call? What's actually happening there?
That is human behavior, and it doesn't get software updates every six months. So, if you can master that, if you can learn that, you can start to adapt your script, you can start to adapt what you're doing and make it work and stay ahead of the curve. That's the thing with these trends; when they happen, what worked two years ago doesn't work today, but it didn't happen like that—it wasn't like a light switch. It happened over time, right? So you want to be on the front end of that, and knowing the psychology behind cold call and sales psychology in general is super powerful.
So, I don't recommend using AI to coach your calls—or at least not over-relying on general AI to coach calls. When you have tightly defined verticals and a lot of training, you can get into call coaching, but the challenge with AI is it's pulling data and information from everywhere. It pulls content from all over the web, and even if you're watching this on YouTube, a lot of great YouTubers suck at sales. Like, we—I've watched very popular people on YouTube say shit that's just completely inaccurate. Well, the problem is AI is sometimes pulling that content in, and it doesn't always know it's not MSP-specific, and do you know if it really works or not? So, like, I don't say use it to coach; don't avoid using it, but take it with a grain of salt.
But what AI is really good at is making you a student of psychology—not the tactical "What's this word exactly right?" It was the thing that drives tactics. What is the thing that drives the tactical changes that are happening when tactics start to change in order to work? What is driving that? And knowing the psychology behind cold call and sales psychology in general—super powerful.
So, AI teaches kind of like the foundation of the craft, the psychology, all of that. Now here's the two prompts that I would recommend for that. One is the teacher piece, and what it's suggesting is take a piece of a call or take a call and say, "Why did this person do this? Like, the objection comes up." It's less a matter of, "Hey, what's the perfect rebuttal for this objection?" which I don't think, unless it's highly trained, I don't think AI is terrific at—may give you some inspiration. But instead, why did that person say that so quickly? What's the psychology behind it? And that allows you to understand at the foundational level, "Ah, okay, that's why that's happening." And then you use the other prompts or the other skills we're talking about to turn that into action. The teacher prompt, kind of like the others: "Give me a course, give me a 30-day curriculum," using these things. And we give it some direction here. Again, feel free, hammer away, change this up, but if you're not sure how to leverage this right, just use the prompt that we have. This will give you a good curriculum to get rolling with. And then if you really follow it, it'll rabbit-hole into a whole bunch of other stuff.
Skill number four is AI orchestration, or let's just say like prompting AI. Most people use AI like they use Google. They type in like a very generic or very vague question, they get a vague answer, and then they blame AI. The top people leveraging AI today, and the SDRs who are going to be upskilling in the role tomorrow, use AI more like they're directing a really smart employee.
They're giving context, they're giving constraints, they're giving examples, they're giving follow-up corrections and tweaking things, and that really is a meta-skill. And it compounds every other skill on this list because once you know how to do this really well, you can go back to our own prompts and say, "I'm gonna make this better. I know exactly how to make this better." That's why it'll change the value of the content that you get out of AI significantly, and if you can prompt better, then you're going to get better research, better messaging, better call preparation, better follow-ups than somebody who's just putting in a really vague question.
My wife and I are on opposite ends of the continuum when it comes to technology. I'm a nerd boat; I'm an early adopter. I had an AI wearable device a year ago, so I'm on that side of the curve, and my wife is on the "not interested" side of the curve. If we both go to GPT to ask a question about where something is or how something works, we're going to get vastly different answers because my wife uses it much more generalized, and I use it like I'm engineering something—a whole bunch of context and everything. Well, the quality of the output depends on the quality of the input.
So I've got two prompts for you to leverage this. One is going to help you look at some prompts that you've already done and say, "Hey, how could I have done this one better?" So just go into your ChatGPT, grab or your Claude, grab a few of your recent prompts and say, "How could I have done this one better?" It'll give you some specific examples that are really good to learn from, by the way.
And then, like all the others, build me a curriculum. I want to prompt AI tools like an absolute pro, and so I want you to give me examples and give me specific instructions from OpenAI, from Anthropic, from the people who built these things. They have a ton of resources out there to help you. They have said, "This is how to prompt," or "This is how our engineers are using it." So, it'll grab that, turn it into a course, and then make it relevant for you.
Then the fifth skill: MSP Buyer Business Acumen. This is one of the deeper moats that you can build against AI, and it is understanding your customer's world better than AI does—not at an information level, I mean it at like the human level. Because that's who you're talking to, right?
And so for you, that means understanding the small business owners that you are actually calling. Take time to actually understand that. What keeps them up at night? Have you thought about that? What does their P&L look like—their profit and loss? What's that look like? What's downtime actually costing them? You're selling IT services; what's downtime actually cost a dentist's office, or why would they want IT, or what are some of their challenges? What are their cybersecurity insurance requirements? What are the cybersecurity insurance carriers providing or requiring right now? What does an optimal setup look like? What are the symptoms of a shitty setup?
The more that you understand your buyer, the person that you're calling, the harder it's going to get for AI or for other SDRs, more importantly, to replace you on that, okay? This is what supercharges you because all of this feeds the rest of it. The more that you understand, the better that you can prompt. The better that you can prompt—like it's a chain reaction.
So, this is a skill that bridges you from SDR of today to SDR of tomorrow and, by the way, bridges you from SDR of tomorrow to AE or sales rep or wherever you're going to be going in the sales world, because understanding the customer is at the root of every aspect of business—marketers, the ops, all that stuff.
Two prompts like the others: "Your cybersecurity insurance underwriter who's reviewed 500 business policies. Here's the industry that I'm calling, and basically explain in plain English the top five reasons a—" and you put in your market if it's different, "such and such company is losing sleep over their current IT setup," and a little bit more on this. Tell me why IT matters. You can go do that right now.
And then, as with all the others, build me a 30-day curriculum. I want to understand my market, I want to know the people that I'm calling, build me a curriculum to actually understand it. And then we've got a bunch of stuff in here.
Real quick, before I close, I'll say this: I don't know what your day-to-day looks like, right? Like you're all part of our program, our SDR program. I don't know what your day-to-day looks like at the company specifically that you work at. Like you're all at different MSPs, different leadership, different processes, different levels of flexibility, I get all that.
Some of you have been with your company for three years; some of you have been there for three days, and some of you are in the US—about half of you, I know, are in South Africa—and you have slightly different rules within your company.
So, don't walk out of this presentation and log in tomorrow and start doing all five of these things on company time without talking to somebody, right? Talk to your sales manager on our side—like one of your fractional sales managers. Talk to your manager at your MSP, tell them what you're learning, tell them why you want to learn, tell them what you want to try, send them this video. That's fine.
Because here's what I'll tell you: having met almost every MSP owner whose SDR is on this call right now, if you bring them a smart plan and a specific skill that you've been building—you've said like, "This is what I've been studying for the past month, I've gone through four weeks of curriculum"—and you bring them a little bit of proof and a plan that it's going to lead to more meetings getting booked and more sales coming in the door, I would bet heavily—I'm betting heavily—that they're going to say one of two things: "Yeah, let's do it," or they're going to call me and they're going to say, "Did you put them up to this, and what do you have the SDRs doing, and should I do this?" And I'll say, "Hell yeah! If you've got a good plan and you guys have been upskilling and you've got a plan to bring better, more targeted, signal-based prospecting lists into the same—dude, let's go! Like, hell yeah!"
Either way, the answer's the same: invest in upskilling. No matter what, you as the SDR, upskill. We'll figure out how to apply it where you are, and one thing I'll tell you is, like early in my career, the most important thing that I ever did was do things that weren't in my job spec before they were my job spec. I did things before I was asked to do them. I upskilled before I was asked to upskill, and that's what enabled me to just—my career trajectory was fast and it was up, and that was one of the number one things that I did. I was just hungry for more knowledge and more skills, and so I hope the same for you.
So back to where we started: two SDRs are going to walk out today. One spends the next 12 months arguing on LinkedIn whether AI is coming to take your job and doing the same script that you did last year, watching your numbers slide and job get harder. The other picks one of these teacher prompts, opens up Claude, opens up GPT, and starts the 30-day process.
And one of those SDRs is going to be on the same call when we're on this next year, and one isn't because as the numbers get worse, sales is a numbers game. I can't choose for you. Your sales manager can't choose for you. AI, sure as shit, can't choose for you.
So this is, to me, this is the most exciting time to be a salesperson in the history of the world. I've not been around for the history of the world, but I really believe that. I think this is really exciting, but there's two paths here, and I think that that's going to be true of AI in general, but that's another video. So use it or get used by it.
If you want the slides or the prompts here, go ahead and grab those at mspsalestoolbox.com. You put in your email, it'll take you to a folder. That folder, like I said, has a bunch of resources in it. This is going to be one of those resources. Feel free to also browse around and check out all the other resources. You maintain access to it for free. Happy to take questions, and if you have any questions about MSP Sales Partners or what we do and the group of people that we're talking to—for those of you that are watching on the camera—mspsalespartners.com is the website. Thank you.