The way that prospects are searching for a new MSP is changing. AI is now playing a key role in the research phase, and I’ve got three things you can do today to keep up. Also this week, discover the one action that KILLS sales for MSPs, and the mistakes you’re likely to make hiring your first sales person.

Welcome to Episode 317 of the MSP Marketing Podcast with me, Paul Green, powered by the MSP Marketing Edge.

Does AI recommend your MSP?

The way that prospects are searching for a new MSP is changing dramatically. The old way where people just went onto Google and did their own research is increasingly being replaced by the new way, where someone gets AI to do the research phase for them and then just validates the suggestions made. That means you need to understand what the AI insisted buying journey is and make sure your MSP has all the correct marketing resources in place. You know how for years we’ve all been obsessed with SEO, search engine optimisation. Getting your keywords right, building back links, and just ranking higher on Google. That’s been the game for years.

The game’s changing again, and if you’re not watching what’s happening with AI discovery, you could slowly find your MSP disappearing from view.

Let me explain. So I was recently reading a pretty cool newsletter and it was about a company called, I think it’s pronounced “Docebo”. They’re not in our world, they sell something called a learning management system, goodness knows what that is. But they’ve been quietly killing it frankly, in a new world of what’s got many different names but seems to be being called “answer engine optimisation” or AEO. You may have heard me refer to it before in videos or on the podcast as GEO, but let’s call it AEO, answer engine optimisation, from here on forward.

In simple terms, this is all about being discovered inside AI tools like ChatGPT, Copilot, Gemini, or Perplexity. That’s where many people now are now going to do their research. So instead of just going onto Google and typing What’s the best MSP for me or IT support near me, they’re asking ChatGPT, What’s the best IT support for a 20 person business that’s a legal practice or something like that. To use the example I was reading in the newsletter, they’re going on to ChatGPT and saying, What’s the best LMS, learning management system, for a 500 person company with a remote workforce? And if you’re not one of the companies that the AI mentions, then you don’t even get a chance.

So that company I was telling you about, Docebo, they noticed this some time ago and they decided to go all in on giving AI the resources it needs to make sure they come up in that AI research. And now nearly 13% of their high intent leads, that’s a bit of a marketing term for people who actually go on to book demos, so for you a high intent lead will be someone who books a 15 minute call into your calendar. For that company, 13% of their high intent leads are now coming from AI discovery that’s gone up 400% in a year. And they’re doing this, because they’re a big business, but it’s all being powered by one person in their marketing team using the right strategy and a bit of clever AI automation.

And here’s what I really found fascinating from reading this newsletter. They realise that the real battle here is no longer about generic keywords or anything like that… it’s actually about brand. So when people are using AI tools, they’ll get a recommendation and then they’ll take the brand and they’ll go onto Google and search for the brand name directly. So this company Docebo, they shifted their focus from trying to rank on Google for best LMS, which is their keyword, to making sure that more people actually knew their name, Docebo, which is a big mindset shift in your marketing. And if you’ve had an SEO driven strategy, you might need a similar big mindset shift.

Because it means that the most important metric isn’t how high are we ranking on Google, it’s how many people are searching for our own brand. In other words, your reputation becomes your SEO. So you run an MSP and you might be thinking, well Paul, this is fascinating, but we are not playing at Docebo level, and of course you’re right. But this shift does affect you too because over the next couple of years, as we go into 2026 and then 2027, your prospects are going to stop Googling IT support this town or near me, and instead they are going to ask their preferred AI tool, Which IT companies in my area have great customer service and specialise in cyber security. And if those AI tools don’t know about you, if they can’t find enough trustworthy, well-structured up-to-date content about your business, then you’ll vanish from the shortlist before it’s even written.

And that’s why now is the time to start building your discoverability. So I’ve got for you three things that you can do…

Number one: Keep your website content fresh, structured and factual. So AI tools, they love data tables, they love clear headings in blogs and they love real case studies. Make sure you’ve got plenty of that on your website.

Number two: Make sure your brand name is mentioned in lots of the right context, so obviously on your websites, but also if you can get other articles written about you elsewhere. Obviously if you can get mentions on review platforms where they actually put the business name in, that would be fantastic if you can get your customers to do that. And you might even try and build up mentions of your MSP in forums like Reddit or Quora. Not because the humans are going to go there to look for you, but because it’s going to help with your AI discoverability.

Number three: Focus your SEO more on who you are and what problems you solve, rather than chasing random keywords that don’t convert. So yes, SEO is still going to be a thing going forward, but I think this is quite exciting because it’s hard if you are one of 50 or 60 MSPs in a town and someone else is already dominating traditional SEO for keywords, this is great, because now you are focusing your SEO on making sure that more people know about your MSP. And this company Docebo’s research and success in fact shows what’s possible. They’re now generating pipeline and leads and clients from AI searches, and they’re doing it right now. And they’ve done it not by gaming the system, but by creating genuinely useful high-trust content that AI can easily understand and find and surface and pass and turn into research for people.

So here’s my opinion, just as we all have to learn SEO as part of our marketing. It’s something we’ve all had to do over the last couple of decades. Now we’ll all need to learn AEO over the next few years, and this really is the start of the next big shift in online visibility. And if your MSP isn’t being mentioned by the machines, it might as well not exist.

This one action KILLS sales for MSPs

There’s something that all MSPs do because it quickly solves a problem for a client, but it’s a disaster if your client watches you do it. It can completely change their relationship with you and actually make it a thousand times harder for you to sell them more strategic services in the future. So what is this thing? You’re going to laugh when I tell you because it’s something so simple, yet it is so dangerous. And I promise you that by eradicating it, you’re going to make more profit from your existing clients.

I subscribe to hundreds of different email newsletters. Anywhere I can see value in learning from someone, well, I’m happy to be on their list and I dedicate just a little bit of time each day to reading email newsletters that top up my brain. Now, recently I got an email from a guy who actually writes good advice about productivity for high achievers, but I did a massive double take when I saw this in his email. So let me read it to you.

It said, Hey Paul, you’ve probably heard the hype. Wake up at 4am and you’ll dominate the day, crush your goals and unlock next level productivity, right? Well, let me tell you what actually matters. This is what he’s writing in his email. He says, I’ve been waking up at 5am since 2013 and recently shifted to 4am when I started driving for Uber in March of this year. And here’s the truth, it’s not about the clock, it’s about what you do with the time once you are up. So that’s the end of his email.

Now, that’s actually really good advice, but just listen to this line once more. I recently shifted to 4am when I started driving for Uber in March of this year. So please don’t think that I’m criticising this guy, and I’m certainly not criticising driving for Uber, that’s not my intention at all. You do what you need to do to survive, right? But this guy, in all of his marketing on his website, he’s positioning himself as someone who offers productivity consulting for high achievers and high achievers do not value advice from someone who gets up at four in the morning to drive an Uber. This is a massive disconnect between audience and message. And it’s no different for MSPs who visit a client site and get their knees dirty, plugging in cables under desks, or they answer the help desk phone for a password reset. Again, this is not a criticism, it’s just an observation.

If a client sees you on the floor plugging in cables or talks to you regularly for low level tasks, frankly they’re very unlikely to ever hire you for strategic technology advice.

You and I know that you can do both levels to a very high standard, but the clients don’t. You’ll make more money and keep clients longer by positioning yourself at a strategic level than you will by being positioned as doing work that anyone can do. So here’s a question for you. If you don’t have the resources to hire someone else to do this work for you right now, what can you do to hide the fact that you still do it yourself?

MSPs: The mistakes you’ll make hiring your first sales person

Featured guest: Robert Gillette founded the MSP Dojo in 2022 after helping a San Francisco based MSP grow from $10mm to $30mm as their lead Account Executive. He also Co-Founded the MSP Growth OS in 2024. Since then he’s helped hundreds of sales professionals raise their sales confidence to have more, better quality sales meetings. At the Growth OS he and his team are leading growth-oriented MSPs on the journey of transitioning from owner-led sales to an organic, predictable, and repeatable Sales Engine.

When I speak to MSPs who’ve been running their own business for 5, 10 years or more, and they’re still doing all the sales in the business, you can understand that one of their goals is to get out of the sales and hire someone else to do it for them. The thing is, when you come to do this, you are going to make a series of very predictable mistakes. My special guest today is going to tell you what those mistakes are, how you can avoid them, and how you can hire the right first salesperson for your MSP, who’s going to make your life easier and generate you more revenue.

Hi, my name is Robert Gillette, co-founder of the MSP Growth OS. I’m the head of content these days.

And it is so cool to have you back on the podcast, Robert, thank you so much for joining us again. You’ve been on the show before and that was under a different business name. You were MSP Dojo back then, and I want to know so much about the MSP Growth OS, we’re going to talk about that towards the end of the interview.

You and I were hanging out just a couple of months ago at ScaleCon 25 in New Orleans. Actually, we were on a big paddle boat thing, which was the VIP night, and we were batting away the insects from the Mississippi river, and we were talking about MSPs hiring their first salesperson, and that’s why we’ve got you back on the show today because that’s a massive, massive subject.

So before we talk about that and all the mistakes that MSPs make when they go and hire their first salesperson, let’s just first of all find out a little bit about you. So tell us who is Robert Gillette?

Yeah, I’m just a dumb sales guy who sold a bunch of revenue for an MSP and then decided that was too much work. And so I now coach MSPs and help them figure out how to get their own growth because sales is really hard for MSPs for very complex reasons.

Oh, it is. And I think that’s a recurring theme on this podcast. We’ve been going, well, we’ve just celebrated six years, and it’s crazy how difficult MSPs find sales. They find it difficult doing their own sales. They find it difficult hiring other people to do their sales. And let’s focus in on that aspect. I think the last time you were on, and we’ll find the episode number that was where you were talking about doing your own sales I believe. In terms of hiring a salesperson, what’s the trigger that makes an MSP think, right, it’s time for me to go and find someone to do this. Is it because they’re sick of doing it themselves or is it because they think someone else is going to do a better job or ramp up the activity? Or is it all of those things?

I think it’s all of those things, but probably the most common one is people that they just hate it. They don’t want to do it. It’s really hard. It’s super discouraging. It’s just incredibly difficult. The activity, the rejection, everything about it is almost the exact opposite of what a traditional IT professional might want to do with their life. And so people start this MSP, and then it grows for a little bit and they get some referrals. And then that comes the point where they’re like, we need more revenue. And then they got to go do sales. And pretty quickly they’re like, I hate this. And so they oftentimes want to hire a salesperson just to abdicate the responsibility to someone else. And that shows up as hiring a salesperson or a marketing company or a cold calling company or someone. It’s just make this your problem and not mine and I’ll give you money. And then that way if it doesn’t work, I can blame you and try with someone else. And that’s probably the most common reason why people outsource this function.

So I completely agree with you there. And actually I think what compounds that and makes it even more of a problem is first of all, when MSPs do hire a sales resource, they actually throw all of marketing and sales at it. So they’re like, oh, great a salesperson. So you can create some audiences, you can do some content, you can generate some leads, you can warm those leads up, you can close those leads, you can account manage them, you can do all of these things. And the other compounding factor that also makes it difficult is the MSP who only does two sales meetings a month, takes on a full-time person and has no other plan to increase the number of sales meetings. What other mistakes do you see apart from those?

Oh yeah. I mean, first of all, two meetings a month would be a miracle for some MSPs I talked to. They’re lucky if they get 10 a year. But I think the other big problem is that they don’t give them any kind of a process or plan to follow. They hire these people that have been really successful in other industries in sales, hopefully. And then what happens is they step into this job and they’re like, okay, well whose example am I following? And they can’t really follow the owner because they’ve never been successful in that role. And so they oftentimes are just shooting in the dark at what may or may not work. And then again, when they’re not successful, the MSP owner has someone to blame that’s not themselves.

Can I suggest something possibly controversial and you can agree or disagree with me on this?

Yeah, please.

You and I have spoken to enough MSPs who even though they don’t do more than let’s say 10 sales meetings a year, they will close six of those or seven of those. And so almost every MSP I’ve spoken to where the owner does the sales, they’ll say to me, if I can get in front of someone, I close loads, I close three out of four or 90%. And someone said to me a few years ago, and it was on this podcast, I can’t remember who it was, but it was another sales expert, there are other sales experts out there, Robert. And they said to me, the reason that they have such a great close rate is because they’re not doing enough sales meetings. So they’re literally getting the most basic number of sales meetings and they’re only meeting with people who are ready to buy, whereas they should be doing 50, 60, 70 of those meetings and getting a 50% close rate. Would you agree with that?

Oh, absolutely. I think the snarky way I frame it is it’s like telling me, oh, every time someone puts a fully cooked steak on my table, oh, I can eat it, it’s so good, I cut it up, eat it. Well, that’s great. Congratulations. You didn’t choke on it. That’s kind of expected. The challenge is what happens when you need to go find people that don’t even know they’re ready to work with you yet they haven’t done all the hard work of identifying the problems, exploring different options, reaching out to their network to find providers that then somehow referred and ended up right on your table. When you have to go do all that other work, that’s what we’re asking, usually a salesperson to go do, is identify companies and create some kind of urgency or need, and then start the conversation, bring them right to your table so you can sign them. And that’s just going to be a lot harder than sitting around and waiting for someone else to do all that hard work, whether it be your prospect or referral partner or a current client or something like that.

Yeah, I completely agree. So alright, you and I have done a pretty effective job of just taking everyone down and making them feel terrible. So let’s lift them back up. Yeah, sorry about that. What would you do, and obviously this is what you do, you help MSPs do exactly this to get their sales right, but what would you do? So you’re an MSP owner, you’re sick to death of sales, you don’t do enough sales activity and you’re ready for someone else to do it. What would you recommend?

Yeah, absolutely. First you got to make sure, can I afford to do this? This is a big one because most people hire a salesperson as their option of last resort. They hire a salesperson and they go, God, I really hope this works out because if they don’t, I’m out of money. And then what happens is the salesperson’s performance is judged off of cashflow and not off of what’s a reasonable expectation for their job. And so that’s the first thing I figure out, can I even afford to do this? And then the second thing is, once I hire this person, how am I going to, for lack of a better term, make it good to work here? There’s an old quote that says, people don’t quit bad jobs, they quit bad managers. And so one of the key distinctions is understanding once you hire your first salesperson, you’ve hired someone who’s probably unlike anyone else at your MSP.

Your MSP was started by you as the first employee and you have a culture, you have a love of technology in a way you think and act in the way you’re motivated. And then because of that charismatic individual, you’ve gathered people like you under you. And so you all kind of feel and think and want to work the same way. And then you hire the salesperson who is by their very definition, very different than you. They want different things, they think different ways, they need different tools, they need to be motivated differently.

And so how are you as a manager because congratulations, you’re now also a sales manager, you don’t just have a salesperson. How are you as a sales manager going to create the kind of culture where they’re going to thrive and give them the kind of tools they need, including mentorship to be good at this thing that you’re barely good at yourself? So that’s the next piece that’s very difficult that I would encourage people if you can answer those two questions, how can you pay for it? And then how are you going to make it good? You’re well on your way to success in this area.

Yeah absolutely. And I think, I’m sure you and I would agree, because recalling our conversation of a couple of months ago on the paddle steamer, that the vast majority of MSPs when faced with those two questions go, Oh do you know what, you’re right, let’s not do this, I’m not going to do it. And as the owner, you get trapped in the business continuing to do the thing you don’t enjoy. But of course the quality of that comes down. Anytime you’re doing something that you’ve done for 10 years and you don’t want to do anymore, you’re not going to do a great job of it. So it’s 2026 a couple of weeks away, and this is our last regular episode of the year. Let’s say that someone’s listening to this over Christmas watching this on YouTube, and they’re just going to hit January ready to go. It’s like, Right, I’m going to answer those questions, Robert, I’m going to do this. What are the steps that you would recommend to get started?

First is I wouldn’t make that decision on your own. I’d find somebody who has done this before and has actual repeatable success in this area that can tell you whether or not you’re right to the answer to those two questions. And this is so funny to me, how many times, even myself and maybe this is a uniquely American problem, I don’t know. We all want to be the first to do a thing. We all just want to be the first guy to invent that product or that process or the thing. We want to be unique in some way. And I don’t know why that is. I’m not going to try ever figure that out in my life probably. But my encouragement would be, you’re not the first person to approach this problem and you’re most certainly not the first person that will be successful at it.

Find someone who’s done the exact thing you want to do and then ask them if your plan is a good one.

Because this is the other kind of weird truth about this. There isn’t only one good way to grow your MSP. When you’re under 5 million, there’s like three or five really great successful proven ways to grow your MSP to 5 million from maybe five to 10 or 20, 30, 50, a hundred. There’s fewer ways, but there are still very plausible paths that have been run before by people that are successful that would be happy to share with you whether or not your plan is going to work based on their experience. So that’d be like, just don’t make decisions on it. You don’t have to reinvent this. Find somebody who can help you figure it out.

Yeah. I love this. And it’s a really nice segue actually into what you do because obviously you’ve had a big transformation in your working life over the last year. So you were the MSP Dojo, which was famously the only place where you could go to actually practice sales. And I still think it’s an amazing concept and you were the first to do that. So talking about someone who wonders why people are first, you were the first to do that both in the channel and I think in any sector that I was aware of certainly. But now you’ve obviously evolved that you’ve moved that on. Tell us about MSP Growth OS. So what is that and how do you help MSPs with these exact problems?

Yeah, so businesses that are approaching that 5 million or above that 5 million, we help them figure out their particular revenue generation model. How do they want to grow to whatever business level they want? And this is really hard. There’s this gap, this black hole around six or 8 million that’ll just suck MSPs in and that’s where all their money goes. And then they just fall back to five and it’s very hard to grow past that. There’s also similar ones at around 18 and around 36. And so the challenge is that I now have partnered with a guy who actually taught me how to do this as a sales professional who organically grew his MSP from one to I think 143 million.

We have coaches now on our team that have grown their MSP to 60 million and 163 million respectively. So we have people that can help MSP owners figure out their journey through the forest as they grow to whatever revenue they’re really looking for. And we can help them set reasonable timeframes and expectations and what they can expect at an organisational level as they try and build that new revenue engine. That’s all we focus on. It’s just new revenue. If you’ve got service delivery problems, you go to talk to somebody else.

This is really, we’re just trying to help them figure out how to get the new client revenue and spin up an engine to provide that kind of growth they’re looking for. We do that through recruiting, peer groups, training, and then one-on-one coaching. So just trying everything that we would need to help them find the right people to help them grow their business. And then kind of, I don’t want to say manage them because we don’t always do that, but it’s mostly coaching and then some kind of accountability groups and knowledge base and all that kind of stuff. So I don’t know if that makes sense.

Yeah, that makes perfect sense. I have to say with those kind of big numbers of the coaches that you work with, the size of the MSPs that they grew to, you shouldn’t have called it MSP Growth OS you should have called it the MSP Overachievers Club. That’s what I think.

Well, it’s a little longer of a URL, but that’s fine.

That’s true, yeah, stick with MSP Growth OS. Robert, thank you so much for being on the show. Let’s get you back on again next year. Let’s not leave it till you and I are sat at ScaleCom 26, which is inevitably bound to happen. We’re bound to sit at some VIP event and sit and have a similar conversation, but for now, let’s just tell us how can we get in touch with you. So what is that website address? How do we find you on LinkedIn?

First of all, thank you for having me, it’s an honour. mspgrowthos.com, or you can look me up on LinkedIn. I’d be happy to respond to you there. But either way, I’d love to talk to you even if you’re not at those sizes. We love helping MSPs hit the revenue growth that they’re looking for because for us, it’s the one thing we know how to do and we just love helping people with that. So thank you so much.

The Marketing Minute

Hi, this is Michelle from The Tech Leader Network, and I’ve been racking my brains on how service desk can contribute to your marketing efforts. Here’s what I came up with. Make sure that your positive and negative feedback survey results has some form of commentary. The negative, you can obviously take that away and do something about it, but the positive, have those feed into a wall of love on the website or something like that.

Mentioned links

• This podcast is in conjunction with the MSP Marketing Edge, the world’s leading white label content marketing and growth training subscription.
• Join me in MSP Marketing Facebook group.
• Connect with me on LinkedIn.
• Connect with my guest, Robert Gillette, on LinkedIn, and visit the MSP Growth OS website.
• Connect with my Marketing Minute contributor, Michelle Coombs, on LinkedIn.
• Got a question about your MSP’s marketing? Let me know.