The Future of AI in IT Services (EP 906)

Jermaine Clark from Sherweb returns to dig deeper into MSP AI readiness, sharing actionable steps and practical solutions for IT business owners facing real-world automation and service delivery challenges. Don’t miss insights on how to truly transform your MSP in the AI era.
Uncle Marv sits down again with Jermaine Clark, Sherweb’s Senior Manager of AI Readiness, for a lively discussion about how managed service providers can drive real business results with AI. Jermaine walks through Sherweb’s robust AI initiatives, including training, certification, and hands-on guides for automating onboarding, ticketing, and customer service. The episode covers practical frameworks for integrating AI based on MSP business models, current trends in tech adoption, and strategies to avoid common pitfalls like shiny object syndrome. Jermaine’s insights are drawn from years of MSP experience and a passion for helping IT businesses scale and innovate.
Actionable Takeaways
- Use Sherweb’s 90-day blueprint to assess internal processes, automate repetitive tasks, and create scalable business models.
- Leverage AI agents for automating onboarding, ticket triage, and customer support to reduce human error and boost consistency.
- Focus on upskilling your staff with AI-powered learning platforms, certifications, and real use-case training for team growth.
Companies, Products, Books Mentioned
- Sherweb: https://www.sherweb.com
- Microsoft Copilot: https://www.microsoft.com/en-us/microsoft-365/copilot
- Perplexity: https://www.perplexity.ai
- OpenAI / ChatGPT: https://openai.com
- Gemini (Google AI): https://gemini.google.com
- Slack: https://slack.com
- Microsoft Teams: https://www.microsoft.com/en-us/microsoft-teams/group-chat-software
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=== Show Information
- Website: https://www.itbusinesspodcast.com/
- Host: Marvin Bee
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Hello friends, Uncle Marv here. Welcome back to another episode of the IT Business Podcast, the show where we try to help you run your business better, smarter, and faster. So previously, we had a conversation with Jermaine Clark from Sherweb, and we started to unpack the essentials of AI readiness for MSPs.
So today, Jermaine returns for a deeper dive, helping us to look more into some of the real world challenges, trends, and hopefully help us with some actionable steps that we can do and get ready for this AI thing. Jermaine, welcome back. Happy to be here, Uncle Marv.
Thanks again for having me. Thank you for coming on, and thank you for helping us to kind of get a better grasp on this AI landscape. It's all around us, as we talked about before.
So I had kind of asked you right at the end of the last show was to give us an idea of what AI readiness should mean for us. Let me start by doing this. We ended with Sherweb.
Let me start with Sherweb, and then we'll kind of move along, because people are probably going to ask, what is Sherweb doing to help MSPs implement AI? Well, it's a great question, and I appreciate us starting with that, because it'll help us to set the tone overall, I think. So today, we've got several aspects of it. I think I mentioned in our previous Connect that at Sherweb, we train our subject matter experts to support our partner community.
And what that leads to is that we have people that are trained and understand what's happening in the AI space, whether it's with Microsoft, externally with OpenAI, ChatGPT, Perplexity. And what we do as a company is we provide those resources to our partners in the MSP space to be able to utilize them and learn not only for themselves at their own companies, but then learn how to become those subject matter experts for their customers. So we provide training videos.
We do webinars in collaboration with our MSPs. We then do on-site visits at events. We attend trade shows to make sure that our presence is available.
And the content that we generate, we have ready-to-go guides on here's how you become ready as an MSP in AI readiness, data governance, security. And we provide all of those subject matter experts and their content to our MSP ecosystem. The other thing that we're doing as well is we had a previous academy where you can, a learn academy where the MSPs can go in and certify on the different paths of Microsoft licensing, compute and security, zero trust frameworks, things like that, that would help improve their internal teams to deliver.
So we're rebranding and rebooting our Sherweb Academy now where we will have not only will you have the learning paths, but we will have a tie back to the certifications that would be relevant and available for the MSPs in the space once they go through those learning paths. And they'll be able to have access to that as one of our partner MSPs so that they can upskill their internal team and their staff. And of course, it is being run on a AI first platform that will allow the MSPs not only to learn about the AI and how to use it, but the platform in itself will interact with all of our MSPs as an AI platform.
So it's kind of exciting that we're doing both sides of this with it, where the learning platform is now AI ready and can help and train the individuals that are using it in how to use AI better as well and how to bake it into their business processes and generate revenue from that going forward. Did I see and did I understand this properly that you have a 90 day AI blueprint program? Yes, and we say 90 days, you know, it's kind of like saying you're going to go to the gym and get buff. They tell you do it in 90 days, no problem.
But that's if you commit, you do a little bit every day and you hit the milestones. Right. So the first thing people are going to do to debunk that is, hey, you can't do it in 90 days.
Well, to be fair, if I could learn a language and speak it in 90 days by going full immersion, I think anybody can do a new thing. And the AI is a new language. I would love to say it's one that we're all going to speak eventually.
But you can't do it in 90 days. And it takes you have to put the work in. You've got to review your internal processes, look at your data governance and all of it.
And then when you're done with that, you go and you start using the AI every day into your business processes so that you gain the efficiencies from it. And then in kind of the last 30 days, you go into the mode of, OK, now that I've done this, what do I build that I can automate with the AI in my business? So you've got a full 90 days of how you can kind of roll that out as an MSP. But it does require the commitment.
All right. Let me go ahead and get this question out of the way, because I know that MSPs are notorious for taking on new products and new gadgets and new stuff just because it's a new shiny object in the marketplace. So how do you or how does Sherweb, you know, assess whether these are, you know, genuinely beneficial programs for us? So it's good that you say that, because one of the other things that we are used to be notorious for in the MSP space is taking an implementation and deciding to do it ourselves for a piece of technology that the experts have sold to us.
So whether it's a shiny object syndrome or I can do it myself syndrome, those two never work well together. From a framework perspective. The steps that are in that kind of 90 day plan of how to become effective with your AI is actually based on process and data.
It doesn't say exactly what you're going to do as your business. And I put it in that respect because the reason we wanted it to be open enough is to allow, I cannot, I've mentioned that I've been with multiple groups of peers in the MSP space and none of us ran the MSPs the same way. We sold all the same products.
We did all the same upgrades, but nobody did it the same way. We have time and materials people. We have people that have three people in the company and they outsource everything to some other people.
So they don't have any actual employees internally. We have people who have help desk and that's the only thing they do. And they farm out their help desk to everyone.
Nobody does MSP the same way. And because of that, the whole how the framework is built out and why it's effective is because it says, OK, insert your job information here. Now, every time you look at the framework and you think about it doesn't matter who it is, it's your job function and it's your activities and your executables that you're going to do in that job that you then fill into the framework at each level.
And then you are now the person that's interacting with the framework so that you're going to see the benefit and the return on what you're doing with the AI. OK, so let me now dig a little deeper there, what would be an example of an everyday process or problem that can be approved by these AI? Oh, that's a wonderful one. So let's take customer service as an example.
One of the biggest challenges is deployment for a machine for your end user. Now, if you know an MSP that does that well, where they don't get any complaints about the new deployments, just send them my way. I'd love to hear their side of the story and how they do it.
But there's always something, you know, users want their icons exactly as it was on the old computer. Something's missing with access, et cetera. So an everyday issue there is just think about it as an example.
All the things that can happen on the back end, a new license gets assigned, the email addresses prepared, the user gets login information to get into the machine. When they log on to the machine, they fill out their position. The RBAC or security, the security binding that they have gets assigned.
All of these things are clicks that a human being is doing right now that a machine can do because it's machine to machine. These are all things being set up on the back end. So you can actually automate the onboarding for a user.
And worse yet, off boardings are, oh, what a way to get some tickets in the future from your from the company you're supporting, saying, hey, you guys off boarded this person six months ago and you didn't remove the Microsoft licensing, you didn't remove this, you didn't do that. These are all issues that we experience on a day to day basis. Now, you know what an agent, an AI agent will do in that situation? It will do exactly what is required.
So you can automate that process. You can tell the agent, hey, I'd like you to off board user this at 5 p.m. on Friday afternoon and it will do it at 5 p.m. on Friday afternoon. It won't do it at 4.59. It won't forget while it's grocery shopping and do it at 5.45. It'll do it at 5 p.m. And that right there is one of the things that you can automate immediately.
The second one is ticket triage, something that's super important in the MSP space. Is this a valid ticket? Is it something that's an emergency for the user? How quickly do I need to get to that? And automating that ticket triage where it's the AI's got access to your entire ticketing system and all the information you have for X company. Person puts in a ticket or they're chatting with your AI bot in whatever chat system they're using, whether it's Slack or Teams, whatever.
Hey, I have an issue. Here's what's happening with my machine. Can you help me? Yes.
Here are the things you can do to do that. I will actually go and create a ticket and we won't need a live person for this because I can get it completed. That type of customer service around the triage of the ticket and getting the ticket into the right hand is something an entire dispatcher does today at the human level.
But think about it again. It's the same printer problem from six months ago that this users come in. The AI knows what it is.
It can triage a ticket and it can send the helpful hints on how to solve this quickly. So I'll pause there because that's a huge mouthful. Yeah, it is.
And let me kind of step back and ask this question from a simple layman's point of view, a end user point of view or a stubborn tech point of view. A lot of AI really just seems like automation. It seems as though we're taking the clicks and we're automating them and we are doing, you know, grandiose if then statements as part of this.
So how much of it is AI? How much of it is automation or is it a blend? So I would say all of it is automation because at the end of the day, the AI interface is there to. Help with the communications between the hardware and the compute software and the user. So the AI portion of that is and I say automation because regardless of how you do it, whether the AI is making the automation or humans making the automation, they're still doing the same process on the technical side.
The difference there with the AI is that the AI now understands in natural language what your issue is, at least from how you explain it. And then the AI then goes through that iterative process on the back end and runs the same type of automations. The difference there, too, is now the AI is running it at compute speed and not human speed.
And there's no, how should I say, inference of what, you know, what happened with my coffee cup this morning. So I'm not really listening to the user when they're telling me about their ticket. There's none of the, you know, we are living our lives as human beings out here.
The AI doesn't have any of that. It's this is the problem you've stated. Is it correct? Yes, I will do these steps on the back end.
So the AI is actually governing those automation processes. But the difference here being markedly is that for a regular automation, you have to put it in place. It's if then statements, it's end.
With the AI, the AI gets to decide where that process ends and where it starts based on your triage. So it is a mix of both. But at the end of the day, let's be real.
It's clockwork, cogs and software that's doing this stuff. And it will always be with the AI side. OK, now the next point in that conversation comes to the people that are afraid that AI will make the wrong decision, whether it, you know, something has happened in the past that that got them or they're just fear of it.
What is the hurdle that we as MSPs, you know, run into? Because to some degree, if we put in an AI automation and it's wrong, our customers are going to be pissed. Yeah. OK.
And I'll take that from a kind of parallel with human beings, because I think sometimes we lose the traction. We because we are human, we assume the machines are at fault with that. But it's if we create an automation and we test it and it's functional, we know that going in is going to rinse and repeat that same automation all the time.
There's no reason for it to do anything else. If I put a human being in the same seat and say, OK, for the next 10 hours, all you're going to do is this one ticket, but for 100 different people and you get it there halfway through that process, they're going to start skipping steps, they're going to get distracted and click the wrong button, etc. So I would weigh the facts here, because an automation is if this happens, that happens, go and the machine will follow the automation process the same identically every time, whereas if you put a user in the seat, the user is where we have the challenges come up.
So, you know, they always say, I mean, the old adage is in your security framework or access incidents, the weakest link is the space between the chair and the keyboard. Hi, that's the human being in there because we get tired, we get exhausted. And there's more likely in repetitive tasks.
Now I'm speaking repetitive tasks. It's more likely that we're going to miss something or miss click a button somewhere that will cause an incident, as opposed to the machine doing the automation where it will follow exactly what it knows, which is that automation. All right, so the fat finger syndrome.
Yes, I've been accused of that myself and the whole idea of distraction. At some point, we need a break. We need a rest.
We got to go, you know, hit the restroom, take a drink. And then we forget where we were in the process. So exactly.
So I see that. All right. So.
Let me kind of shift gears here, because I wanted I want to get you excited for a little bit. So what excites you most about the future of AI in our managed services space? Oh, I mean, look, this is this is really awesome. I think I it's interesting that you want to get me more excited because I feel like I'm pretty excited already.
But I think in the in the MSP space going forward, I think we're truly going to get to a point where we get we have the mind space. The mind space in our business is to do things that are truly transformational. And I say that it's you know, most people are probably expecting I'm going to say something like robots are running around doing all the work or something along those lines.
But really, it's to give humans back in the MSP space, the room to develop those niche new things and create something new. If I can come in, I can just see an MSP today. Everybody comes in on a Monday virtually or otherwise, and.
They don't have a backlog of tickets from last week. They're supporting ten times the amount of customers on the same 50 person team that they did five years ago. And when they get in there, they're trying to solve challenges that are overarching for their customers.
You know, where is the technology going to go next? How can we stay relevant? What material do we need to create to upskill our customer base? What are the biggest issues that we're seeing in security? They have time to mull over these challenges and come up with unique and novel ways to solve them while the machines are chugging away at the mundane day to day printer issues and Zoom call issues and microphone challenges. Did you do your updates on your computer? No, please reboot. Like, what's the purpose of a phone call for that? So I think I'm pretty excited because people will have space to actually enjoy the part of their jobs that they like, which is innovation and pumping ideas out that may change the entire way the MSP space looks.
And I'm excited to see what that will look like, because I do predict we're going to be able to automate and or put agents in place to deal with a lot of the day to day challenges, user onboarding, etc. And the service, the experience, I will switch out service for the experience that the end customer is going to get from your MSP. That experience of everything works, things are fluid, the customer service is great, will then lend to more creativity in the space and less of the shiny object fat finger syndromes that we've seen over the last few years.
When you get to speak to MSPs. What's like the biggest things that they're asking you about or what are you most excited to talk with them about? There's two giant questions there. OK, so let's start with what are they asking about? I think I've seen the whole range of questions from, you know.
Do you believe in this AI hype nonsense? It's just another way for the conglomerates to get our money. Security, security is a problem. It's always been a problem.
Why are they making it sound like it's a problem today? We get a lot of those statements. And then on the on the flip side of that, we have, well, how do I actually convince my customer to move to AI or to upgrade their security infrastructure? It becomes a business conversation around how they're going to make me money. How do I actually take this and making money? And.
That's kind of where they are at when they ask those questions. What I get excited about is when they ask those questions, it comes back to one thing for me and the excitement in my in my voice there is. None of your questions that you ask today are how do I implement this internally and turn my team into a super AI driven team that delivers on the service delivery that will close the gaps with my end customer, because why an end customer is looking for quick service.
Problem solving customer service that makes them feel important as your as your client and ultimately that their technology works seamlessly to a point where they can forget about it and know that you have it covered. That type of service delivery is what you can deliver as an MSP, transforming your MSP into the AI space. So with all the automations and the tickets and all the things out there, I get excited about talking about, well, let's talk about your business today.
You want to make more money? Here's how you scale. You take all the real tasks. You give your technicians space to solve the big problems.
You give them time to train and develop. One of the things I hear consistently is, oh, I've got so much work to do and migrations is I can't train. Well, if you can't train, how are you going to stay relevant? So I get pretty I get pretty fired up when I'm saying to the MSPs, I hear your questions.
Let's talk about how we can transform your business before you go fix your customer's business with AI. Let's get that conversation going. Let me provide you the training.
Let me get you the people that can be hands and keyboards to support that. And then let's make you some money doing it, because if you can charge and build the same professional services tech, the same tech for triple the amount available hours because he using AI, he can complete the work in a third of the time, then you're leaving money on the table. So let's go make some money.
So that's what I get pretty excited about when I'm having those conversations, because it makes sense. You've got to do it internally. You've got to be the expert for your customer base.
And that's where you're going to leverage and scale and grow. All right. I'm glad I asked the question that way, because I got the answer I was looking for in a different route, because I do think that we are kind of in a conundrum as an MSP, as an IT solution provider, where we're being pushed to sell, sell, sell.
Your customers are looking for AI. You need to be selling them, whether it's copilot or any other thing. That's what we're being told.
But at the same time, you know, I know we're looking at it from the standpoint of, man, how do we make this work for us and make us more efficient? But we listen, I'm not a sure web member. So I apologize that I don't know what's in your marketplace and stuff. But with my other vendors, I don't know what I can do with their products to make my business more efficient.
Yeah, I can buy more stuff, but I'm like, OK, if I'm using AI, I shouldn't have to buy more stuff. Does that make sense? Yeah, it makes sense. And I'll tell you, you know, you're pulling at one of my heartstrings there because commoditizing technology is not the way that we need to go, especially for myself in the MSV space.
People, I don't sell copilot. I don't sell licenses for Microsoft or any of that. What I do is have great business conversations with interested business owners that would like to understand if I'm going to I would like to move to a desert island and, you know, in the Caribbean Sea.
And I say, OK, that's great. What do we need when you get there? Well, I'm going to need a house. I'm going to need a boat.
I want a helicopter. It must have at least one volcano. And when you think about it, all those things are infrastructure needs.
But all they do is support. The idea of living on a desert island in the Caribbean. And when we talk about AI, when we talk about the tools in the marketplace, there's one hundred and fifty different security tools you can buy.
There's twenty five AI that you can buy from a perplexity to Gemini to copilot AI, chat, GPT, open AI. It is not the AI that you need to buy. You need to have a great understanding of what you're trying to achieve.
And those things are the infrastructure that support your idea. And it supports you to success in whatever you're trying to do. And in the in from a short web perspective, we've been pushing very hard on that conversation because you need a tool set or a skill set or a building set in order to grow and be successful at the idea that you want to be.
And if that idea is to be the best MSP for deployment, great. Here's what you will need. Here's what will support that conversation.
But it's not about the product. It really is about the solution to driving that idea to success that you have as an MSP. So you've got to bring that idea to the to the forefront with it, because a product space is a product space.
I can show you 50 security products that will do exactly the same thing in the same way effectively. But it's not about the product. It's what are you trying to achieve as an MSP and what infrastructure solution, one solution that has all the things in it that will be effective for what you're trying to achieve.
So with all that you just said. I'm sorry, but I'm still stuck on things that I've heard from other vendors, because in the back of my head, I'm hearing, well, you got to have metrics and you have operational stuff and you got to be looking at emerging technologies. And you're right.
I think that the focus has got to be on what can I do. In my business to take advantage of these things and make us more efficient and make us more profitable, and it's hard to do that when it's all about product, product, product, product. So I appreciate you saying that.
Hearing me still regurgitate that, though, how does that make you feel? Well, you know what? Change management's hard. I think if we can, as a species, get people to wear motorcycle helmets consistently, we can't get them to wear seatbelts in cars for their own safety consistently. I think that's just the human condition.
And the people that are some people need to they'll see the new thing and they'll go after it and they'll put their ideas out there and get in on the early adopter space. But then there are the more cautious middle of the bell curve people that will wait to see how things are fleshing out before they put their hat in the ring. And then you've got your detractors on the other side.
They're just like, you know what? That's just another thing. I'm going to put it in the bucket of something else that's just making my day worse. And for now, I'm going to leave it there.
Eventually, when everybody else is on board, they're going to come on board. But only because there's more than enough evidential fact around what they need to do. But by that time, there will be 10 years behind the early adopters and six years behind the middle range.
And when you think about it like that, you've got to decide as an MSP. It's OK to play in your space. Where do you want to be? Do you want to be on the leading edge? Do you want to be in the cushy comfort zone for a long period of time? Or are you all this is not the thing? So really, I don't I'm impassioned by it because I understand how the makeup of the species goes, I would say.
But it's really about your individual experiences. And until today, you didn't know that there was a another way that you could be thinking about it because you haven't spoken to Sherwood yet. So here we are.
Here we are. All right. So now you've acknowledged the fact that people are going to wait.
People are going to be hesitant, blah, blah, blah. But if you were to be able to talk to those people and give them advice about their, you know, apprehension, what advice would you give them to say, look, you need to start your journey now? So I would say that that's a great question. And to everyone out there in the MSP space, I think I would say this, that there's always going to be some form of security threat.
There is always going to be someone who will send determinators for us, put us in the matrix. It doesn't matter what it is. Eventually, though, it was really about your own business and think about your own business and where it is today and think about how you want it to grow and or stay relevant in the near future.
And if you think about it from that perspective, growth in your business, profitability and staying relevant in the space. It'll be easy for you to take a look at what's available and say, well, now I need to do it because if we come back to the infrastructure conversation for me to achieve, stay relevant with my customers, give them value, improve on my customer service delivery and grow my business, I need that back end infrastructure. And part of that is automating my processes and having AI as part of my team.
And that's how I would put it. That's how I would phrase it. It's not necessarily advice.
It is really a reflection on where your business is and whether or not you want to keep it and make more money and stay relevant. Because, you know, you don't want to go the way of Blockbuster or Blackberry where you're like, I'm too big to fail. You know, this thing's going to go by.
Nobody wants a flat phone screen. And then eventually now, you know, the kids of today know Netflix. They know all these online Hulu and all the online services.
Nobody knows what a Blockbuster is. And the relevance of that has been lost. So you got to pivot.
Yes. Very, very good. And adult.
Well, Jermaine, thank you very much. And I appreciate all that you've said. And I know that you mentioned earlier that, you know, you're not selling Co-Pilot.
You're not doing licenses and stuff. But I do want to give you again an opportunity to talk more about Sherweb. We talked about some of the things that Sherweb is doing to help us in AI.
But what would be the last pitch of Sherweb that you'd like to leave with listeners? I would say if you if you do want to partner with an organization that has your business interest at heart and we try to get away from the commoditization of those resources, have a conversation with us. There's no commitments around that. It's come see what we do, understand where we are and feel free.
I used to work with lots of other distribution centers as an MSP myself. So I've been on the other side of the fences on that. And I would say, choose what's best for you.
If the bottom line and cost is for you, no problem. If you'd like to really grow and diversify your business and have a partner in that growth, come check us out at Sherweb. And if it doesn't work, it doesn't work.
We'll be happy to support you in either way. All right. You just made me think of one last question before we end off here.
We did not even talk about your MSP days. But yeah, but before you before you made the switch to the dark side, had you implemented any of these processes in that MSP? The answer is yes. Was there one that I would say it was a really good proofing ground around creating knowledge sources, speaking on AI, training and customers and how to utilize it and testing all of these internally.
Again, we had access to in that MSP to the early access program for Copilot. So the team that I was working with had access to Copilot in, say, December 2022. So they were well ahead of the game and we were able to test it for what it couldn't do, which is just as important as what it could do.
And I would say between then and today, the only difference would be if today were the day we were starting, it would do a lot more of what we were hoping it would do, because initially it was really a growing pains process. And the AI was not, I would say, how do you say it was not prime time ready at that time, and it has grown considerably since. So with that, we were using it for business review meetings.
We were using it to gather data on ticket metrics. We're using it to triage tickets and find ways to fix problems that we've had over a long period of time. So all of those were implemented into it.
And then, of course, we had a mini internal AI committee that would train, share their experiences with each other so that we could make the process better. So, yeah, I mean, we've been doing that for a long time, which is why, you know, I am now an avid speaker on this. It's all from lens, from the experience.
OK, great. Yeah, I was I had meant to ask you about that, but we got to start on other stuff. But I appreciate that and glad to see that your passion has not been daunted by that MSP experience.
So thank you again for continuing on in that journey. Awesome. It's been a pleasure, Marvin.
Thank you for having me on the show. All right, folks, that is going to be a wrap here. And Jermaine Clark, senior manager of AI readiness at Sherweb.
If you want to keep that conversation going, his information will be in the show notes and you can check out Sherweb and their marketplace. And again, they are not just M365. They've got a whole portfolio of products that they offer and support there.
So take a good look at them. That's it, folks. Give us your feedback.
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Jermaine Clark
Senior Manager of AI Readiness at Sherweb
As a former MSP leader, Jermaine Clarke empowers partners to harness AI’s potential for real-world business growth. At Sherweb, he focuses on strategy, training, and ethical AI adoption, helping partners optimize operations and navigate the evolving tech landscape.