Josh Smith | Stop Selling and Start Educating Your Prospects

[00:00:08] Good afternoon, everybody, and welcome to the latest installment of MSP Business School. As always, I'm Brian Doyle, here to be your Sherpa for our conversation today. But we're going to talk a little bit about marketing, one of the favorite subjects of most MSPs and one of the ones they probably struggle most often with. And joining me on the show today is Josh Smith of Wingman, and he's going to talk to us a little bit about, you know, what's working out in the marketing market space today,

[00:00:36] what's not working, and how his organization is kind of taking some special steps to do some different things as well. But with that said, I'd like to welcome Josh to the show. Hey, Brian. Thanks very much for having me. Appreciate it. You bet, man. And, you know, I'm glad that now we were having a couple of technical difficulties before we got started, but you're ringing through loud and clear, which I'm very excited about. So, you know, Josh, I usually say let's kick off.

[00:01:01] And for those that don't know you, share a little bit about your background, you know, what you've done today and how you ended up in the crazy world of MSP. Yeah, yeah. I sort of fell into the space, really. I've told the story so many times now. You know, my family get bored of it. But, yeah, so obviously, as you mentioned, I'm Josh. I'm channel manager at Wingman, MSP Marketing. We're a marketing agency for the IT space. And I came from a finance background originally. You know, I was doing my accountancy exams.

[00:01:30] I fell into that role, as it were, at the time. I did that for around six, seven years. And a lot of people were telling me that I was too fun to be an accountant. I was going to just say, accounting to marketing, that's a huge shift. I was expecting, you know, I was stock broken. I was doing something on that side of life. But, yeah, that's an interesting transition, Josh. Yeah, I did finance in events. So it was a little bit more exciting.

[00:01:59] You know, there was concerts and event days. And there was fun things like that. But I transitioned because I was looking for something more in a people-focused, sales-focused, not sitting in Excel 90% of my time. And I found the job at Wingman by no searching of the MSP space, as it were. I knew of it. Obviously, we had IT firms. We had an MSP at my old jobs. But I found a sales role local to home. I liked the look of the role. I liked the industry.

[00:02:28] It sounded cool. It sounded different. I knew that Wingman, we're based in the UK, but we work across the English-speaking world. And obviously, we'll talk more about that. But I reached out to the director at the time of Wingman and said, hey, look, I have no experience in sales. I'm an accountant. But I'd love to have a conversation about how I can work at Wingman. And then we met online. We spoke a few times in the very British way. We went to the pub and met there as well. And then, yeah, eventually hired me.

[00:02:57] And here I am two and a half years later. And my resume still says accountant because I never had to update it. Wingman had never even seen my resume. So just purely based off, yeah, our personalities working well together. And that's usually the best hires. You know, when we were hiring even for IT personnel, it wasn't about the technical chops often of the folks. But could they relate to people? Because anything can be taught, right?

[00:03:25] But what you can't teach, especially if you're going to be in a forward-facing role, is can I be personable? Can I hold a conversation? Will people know, like, and trust me, right? And certainly in the world of marketing, which gets good and bad rap sometimes, right? You know, it's important to have somebody that, you know, that an MSP can feel comfortable, you know, having the conversations with, even the tough ones. Yeah, 100%. You mentioned it there.

[00:03:52] You know, I've always been a big fan of far-on personality, not skill set. You know, you can teach the skills, especially from you guys, you know, that first-line tech. There is a person at the end of that phone who's got a problem with their laptop. They don't need someone overly techy to explain to them what the issue is. They just want someone to reassure them, you know, be understanding that it's a person and say, here's the emotional side of it. I'm going to fix it for you. And like you say, you can teach the tech side of it to a certain degree. Of course, you know, third lines aren't going to like me saying that.

[00:04:21] But there is a certain level of it. It's the person, isn't it, more than anything else? No, and it's true. I mean, but that's really any industry, right? You know, things can be taught, but true blue people are true blue people. That always comes through. And obviously, they took a chance on you, and it seems to be working out so far. So that's kudos to you. I'm learning your part. So let's kind of shift gears a little bit, and let's talk a little bit about marketing, right?

[00:04:49] You know, there's a lot of interpretations of how marketing in the MSP world should work. And it's probably one of the biggest mysteries for MSPs, too, you know, because there's so many different voices coming at them. Go local. Go national. Go bigger. You know, like there's all these different push and pulls. Use AI. Worry about SEO. All this. Tell me a little bit about what you're seeing these days and how you are approaching, you know, the marketing conversation with your customers. Yeah.

[00:05:18] So marketing's changed over the years, and obviously, I've only been here two and a half, but I know the background of Wingman. And, you know, we've had to pivot very much like the MSP space. You know, you guys were break, fix. Then it was support, and now it's cyber, or now it's AI. And we've been the same. You know, we very much started as a lead gen agency, pure cold calling, nothing really much else to it. You could get a list of people, call them, and probably book an appointment. Now, it's a lot harder, of course. You know, a lot of MSPs grow off referral.

[00:05:47] You know, they get to that point of word of mouth. Sort of either maybe runs out or, you know, dries up or it's not as consistent as you'd like. And then there's that question of, oh, now how do I do marketing? We spoke before about the personality of most MSP owners is techie first rather than entrepreneur. Yeah. And the biggest stall point for MSPs is owner goes through their Rolodex, gets to the end of it, and they don't really have a marketing concept or a sales concept.

[00:06:16] And just bringing people in isn't the answer because if there's not a process that they can follow, it's a challenge. And let's face it, you know, new salespeople coming in, new marketing vehicles may not be as successful as that referral, you know, business. But that's obvious. You know, referrals are already coming in with no like and trust, and you need to build that now when you're going out cold. Yeah, 100%. We talk about everything through like the sales funnel and, you know, referrals come down halfway.

[00:06:46] You know, they're already there. They've gone past that audience stage, that trust building phase. They're just ready to have a conversation. And most MSPs will take on any bit of business that comes their way because why would you say no? And I think you mentioned there about niching or, you know, going national. I think the big thing for us as two probably levels to it is that niching down to a particular industry and a particular audience that you really understand their paid points. Exactly, you know, what we do. We're not going to argue against niching.

[00:07:12] But it allows you to have a bit further reach, I would say, location-wise, you know, geographically. I mean, we're based in the UK, but 70% of our market is in the US. And that's only because people don't care that we're over the pond. We're however many thousand miles away. They just care that we know MSP and we understand their problems. Yeah, as we chatted prior to recording, COVID really brought the world closer, even though we were all isolated in our living room, so to speak, right?

[00:07:39] Because we all got comfortable with vehicles like this being on video, being on camera, which we wouldn't have been comfortable with prior to that. And it really made us move from best person in my region to best person I can get at the price that I want to pay, right? And certainly opened up for marketing agencies, opened up for the service community. But at the same time, I want to focus on something you did touch upon there, that niching piece.

[00:08:06] Because so many MSPs that I talk to, they will be generalists. Yet you talk to them and you'll find out they have two or three accounts that are very good accounts for them, and they're on the same vertical. And it's like, why are you not focusing on expanding on that, that you already have invested this time and knowledge into? And sometimes that simple statement becomes a revelation, which is always amazing to me. Yeah, it's crazy.

[00:08:30] We speak to a lot of MSPs about doing a sort of task internally of who are your most profitable partners and who are your most painful. And it's sort of like a little square, and it's like most profitable and pain-free are up here. We want more of those. But so many of them will take on the most painful and least profitable because it's a new client.

[00:08:51] And I think doing that task internally, a lot of the time we'll sit with an MSP, we'll do that task, and they'll suddenly go, oh, I've got 15 CPA clients that they're all quite happy and they pay me good money and they're quite profitable. And I'm like, oh, shall we aim to get more of those? And then again, you can focus on that market. They've got particular pain points, of course. And then you've had people on here talk about video testimonials in the past, and they're huge for us as well. We do that with pretty much every client we can.

[00:09:15] And if you can have a CPA on your website talking about all the things you helped with and all the pains you helped them through, and then a CPA comes to the website and they go, they either know the other CPA or they say, hey, I've got all those same pain points. It's just that credibility and that trust that we mentioned. Yeah, I mean, we never want to put our customers in a box. They all have their unique characteristics. But really, at the end of the day, most accountants are using similar technologies across the board as our doctors, as our lawyers.

[00:09:44] You know, the groups that we serve as an MSP community tend to have very similar traits. And, you know, there might be two or three pillar applications that differ, but the core is very much the same. Yeah, definitely. And I think then it just allows you to branch out a little bit further if you've got that focus on CPAs. You know, it's not he's the most local. It's, oh, no, she's the best fit, like you mentioned. You know, she might be 100 miles away, but she really understands me. Right.

[00:10:10] Now you can focus in on those secondary traits like, oh, I only want to work with accountants that are using these tools. And now you can broaden that search, obviously, and really get very prescriptive about it. So now we've identified our ICP. How is, you know, how is a group like Wingman going after and helping their MSP community get message out to those ICPs? Yeah.

[00:10:36] So as I said, we started as purely lead gen and that worked back in the day, but now it's so much harder. You know, trying to get people to change MSP is like changing bank, isn't it? You know, we all know how hard that is. And it's, you know, they even need a huge catalyst, like a huge cyber breach, and they realize that actually their MSP is not very good or, you know, their MSP has been acquired and they got on with the owner, but now transitioned away. And it's suddenly like, how do we get that catalyst to happen? And we're now very much a full service sales and marketing agency.

[00:11:04] So we do everything from, you know, website build and branding and messaging all the way up to, you know, we have SDRs on the phones for our clients, event planning, which is a big strategic move for us as well. SEO, you know, everything in between, because there's a multitude of touch points that you have to have with a prospect before they're suddenly like, okay, I trust them and I'm ready to buy. You know, people don't do it. And you've spoken about this on the book before. Blasting emails out to everyone and everyone hoping that someone takes a bite.

[00:11:33] Especially in the MSP world where it is a trust sale. Everything that you talked about, about an MSP or a customer won't leave the MSP is so true. It's one of the harder sales out in the marketplace only because it's about timing and trust, right? And those are things that trust can only be built over time. And timing has to be, I'm in them with a rhythm enough that I'm there when it finally becomes that moment, right?

[00:11:57] Right. And those are two things that can be difficult for a single salesperson, as an example, to do or without a marketing support team that's keeping awareness, at least, in front of the customer to get that job done. Yeah. And a lot of MSPs we speak to are really good at that sort of like top of the funnel. You know, we work everything through the funnel because it's, everyone knows what the sales funnel is. It makes most sense. And a lot of MSPs are great at that audience and awareness piece at the start. You know, they have blogs, they have socials, maybe it's from a vendor, maybe it's from a service.

[00:12:27] And it's great, but it doesn't then move the needle. It then doesn't get someone to actually have a conversation with you. And what we found over the last couple of years is the pivot to events has really, really helped. And not just, you know, a support event or a vendor paid for event where we're talking about a particular product. It's more around AI we've found has been the biggest differentiator. It's like I mentioned, support versus support. It's always going to be a hard sell and trying to convince them that what you've got is better.

[00:12:52] But if you can add a service offering to what you're doing, and it doesn't mean you have to be an AI expert, and it's still very new. I don't believe that anyone's really an expert yet. There's still too much to learn. But it's something that gets people in a room, you know, that FOMO piece of art. And it's something that we've never really had in the industry before. People are solution aware, but they're not problem aware. You know, they know AI, they understand it, but they're like, I don't know what the problem is that AI fixes just yet. The opportunity wasn't as big back in the day.

[00:13:21] But when social media first really started coming on the scene, it was that thing that was unknown to the business owner. So they would be more than happy to attend an event about how social media might impact their business in the early days. And MSPs were almost doing that as a value-add driver to get people in the door and start building relationships. The benefit today is AI directly lines their pockets too. But the customers, I think, are coming for the same reason. And this AI is this animal, this mystery.

[00:13:50] And as traditional business people, they understand it. You know, I've used it for generative for a long time. Or, you know, I've done, you know, my kid's done some really cool pictures with it. But I don't think any of them really understand how to harness the horsepower to drive different processes in their business. And that's where the MSPs can really, you know, get them in a room, share, you know, that concept, share a task that they might be able to tackle through AI, and then start broadening the conversation. Yeah, exactly.

[00:14:18] And the broadening piece is always the one, you know, a lot of our clients worry that they're like, oh, I'm not an AI expert. I'm scared to talk about AI with my clients. I don't know enough. And we're like, you know more than your clients do, definitely. And also, it's even down to like policy, you know, and that comes from then compliance and then cybersecurity. A big one we do at a lot of our events is talking about AI policy and how many of your staff use AI? And people say, no, they don't. And they'll be like, is anyone using chat GPT? And everyone's hand goes up suddenly really quickly. And it's like, yeah.

[00:14:47] And do you know what they're putting into it? And are they on a free version, right? You know, there's so many different outcomes that can come out of that. But go for it. Yeah, no, I was just going to say it's just then, you know, everything else dovetails into it. You know, the cybersecurity conversation comes off the back of it. The compliance conversation comes off the back of it.

[00:15:06] And then suddenly you're opening up all these doors and you are someone talking to them about something that their MSP probably a lot of the time isn't currently talking to them about because they're too scared to or they're not offering that service. And like I say, it's that people get people in a room. You become the trusted advisor. People don't want to book a sales call with a salesperson. There's partly a reason my job is called channel manager rather than sales manager because people will have a conversation with someone who they don't feel they're going to be sold to.

[00:15:33] If you go to an event and it's an education event, you feel like that MSP is teaching you something, giving some value. You know, the more than likely you'll engage us. Yeah. Yeah. And, you know, I love the line that you said there. You know, the reality, I always go back to the courtroom, right? You know, to be an expert witness, all you have to do is know more than everybody else in the room about that topic. It doesn't mean you're necessarily an expert.

[00:15:55] And that's the opportunities MSPs have today around AI is you know more than your customer probably does just because you're piloting things and you're exploring it within your own world. Take that knowledge and help them get started. Yeah, 100%. I'm definitely going to use that courtroom example there. Absolutely. And don't even credit me because I'm sure I stole it from somebody else. I'll have to go back and find out who you stole. It's such a truth.

[00:16:25] Like, you know, I think that's one of the biggest things that, you know, the MSP, you know, owners in the MSP that are technical led, they feel a little bit of that imposter syndrome when they go out to sell sometimes or when they want to hold business conversations. And I always have to remind them, you're a business owner too. Just talk about what you're going through. And you're probably the guy sitting across the desk is going through something very similar. And, you know, those are the bonding things in a relationship that can help grow them.

[00:16:52] And then what your groups do is really help put the structure to it. And I think that's where the MSPs often fail. They either don't have the bandwidth to put the structure or they don't know how to appropriately put the structure. And I think if you're an MSP like that, you got to go outside. You got to find a group that you, you know, you trust to handle that for you. So I'd love you to talk a little bit about, you know, what are some of the events you're putting on with MSPs to get that in? Is it a lunch and learn type situation?

[00:17:21] Is it tied to a, you know, to a game or, you know, some other type of event? Or are you getting people coming in just for the knowledge? Yeah. So probably a mix of all of them depends on our MSP client and depends on their client, I suppose. You know, one of our clients is very law focused. They only work with attorneys. And for them, it has to be a serious enough event that they're going to pay attention to. So it has to be, you know, a lunch and learn to talk about AI.

[00:17:48] And then, of course, in the room, we'll give them some free education. I mean, and you mentioned about imposter syndrome. A lot of our MSP clients are even too scared to get up on stage at times and run the room. And our team have even gone to events, put on the T-shirt of the MSP and got up and done a little talk just to, again, get the ball rolling and get the flow going in the room. But then we've done evening events, you know, dinners with some more of the bougie events, if you will. And then we've done, yeah, morning breakfast.

[00:18:18] It really depends on the audience and who we're trying to get in the room. But predominantly, the topic seems to be AI that's getting people there. It's just the phone line. You know, people are like, everyone's talking about it. What can I actually do with it? And then when we get people to the room, they tend to be interested. Yeah. And we see, you know, we've had episodes that have talked about this. The MSP doesn't even have to have a full plan of what they're going to attack. It's really, are you ready to implement? And then how are you going to manage and govern it long term?

[00:18:43] And if they even just stayed to that conversation while, and then let the details sort themselves out, they're bringing value. And they're bringing it in a way that they're used to talking about anyway. Exactly. Yeah. And we found that, you know, we'll do a multitude of different touch points to try and get bums on seats for the event. You know, we do LinkedIn ads, email campaigns. We even get our SDRs calling businesses and say, hey, do you want to come to this free event that we're hosting?

[00:19:08] Because people obviously engage in different ways, but there's always a different touch point that we need to try and get someone to be there. Someone will, you know, it's the benefit of the event side as well is that people don't teach it as like MSP marketing. It's more like product marketing because we're marketing an item that someone could go, oh, I want to go to that event. Yes. Rather than a, do you want IT support? And it's like, no, or I'm not ready to have that conversation. So that's the benefit of the event.

[00:19:35] It's less, they have to have less trust to get them in the room. You know, they need to know less about the brand. And if we put on an event about AI and marketing, people don't necessarily care that it's Wingman doing it, but they find out it's Wingman in the room. And then we have that conversation. Whereas if I try and get an appointment, it's like, oh, why should I have an appointment with Josh from Wingman? That doesn't make sense. And I don't need that right now. So that's where the psychology of it is so funny. Well, Josh, we're getting near the end of our time. And I certainly want to make sure that you can cover off on anything that we haven't talked about today that you want to share with our audience.

[00:20:04] And so, you know, are there other things that your group is doing that you want to make sure that our audience is aware of? Yeah, I mean, there's a few transitions, obviously, over the last few years. Like I say, we are a full-service sales marketing agency, so we do cover everything. Even if teams have got an internal marketing person, we'll still work with them as well. But I think some of the transition as well on SEO to AEO, GEO, HEO, whichever acronym you want to use.

[00:20:32] I actually quite like HEO, which is hybrid engine optimization. I quite like that one. But trying to work for the LLMs, you know, people obviously are starting to search and engage on the internet in different ways. I'm definitely notorious for I use ChatGPT for everything, you know, for my travel, for restaurant recommendations, for everything. I will ask it to tell me everything I need to know. And that's similar. You know, people are doing that for the MSP market as well. So we've definitely seen a smaller transition going towards the, you know, some of our clients have found business off the back of,

[00:21:01] I found you in ChatGPT as an example. But I would say there's less so people looking, obviously, for MSPs. You know, a lot of the time people aren't going to market to look for it. That's why the events can work so well. But you've still got to be found when people are searching. So, yeah, the transition from SEO to GEO, Google's not dead, not by any means. But people are searching in different ways. And you've got to try and cover all the avenues for sure.

[00:21:25] So we've definitely seen as a product house the move in, you know, with our customers being the technical community, the move to AI has been fast and furious from a search standpoint. You know, we still see a lot of information coming from SEO, but we're definitely seeing that there was some transition in numbers till we kind of retooled and retrenched as well. And I'm sure every MSP you're working with seeing the same thing. Yeah, yeah, for sure. And, you know, we use like different lead tracking software on all our clients' websites

[00:21:55] so we can see where people are coming from. If people are engaging but they're not clicking on something, we could reach out to them. But, yeah, you can even see now it's Referralink, ChatGPT, Gemini, you know, Codefile or whatever it might be. Josh, you know, the last thing we always like to close with is a little bit about work-life balance. You know, the MSP industry can be a bit of a burnout, even though we sit on the periphery as vendors, it's still a very similar, you know, approach. How do you kind of maintain the mental side of life?

[00:22:25] Yeah, I'm definitely still working on this one. I think we're in progress, right? I'm not great at switching off. I think it's from my finance days, of course. You know, you get an email about something financial. It has to be dealt with. So I've always been bad with that. But I think what I found works for me over the last couple of years is putting personal events in my work calendar. I found that that's been a real understanding of, okay, I need to leave at five on this day because this is happening, not just because, you know, it's busy in my calendar year or it's five. Yeah.

[00:22:53] And working with the U.S. and Canada markets, of course, you know, for example, Pacific time for me, you know, it's 5 p.m. here, but it's 9 a.m. for them. And I know that I need to have that work-life balance. But the personal, yeah, meetings, personal happenings, you know, birthdays, dinners. The pros and cons of global warfare, man. It does. Yeah, you follow the sun. Yeah, exactly, exactly. So, yeah, you know, even if it's I'm going for a run with one of my friends or we have a wingman run club,

[00:23:22] you know, a few of the team go out for a run every couple of weeks or once a week. And even just putting that in my calendar just reminds me that there's other things happening, you know. Oh, I need to put that meeting four to five, but I need to be gone by five because something nice is happening and I can sort of find that balance there. Awesome. Well, Josh, really appreciate you coming on today. For the listeners, we'll be putting Josh's LinkedIn address as well as a link to Wingman so you can visit the agency as well.

[00:23:50] I encourage you to reach out to him, ask some questions, get engaged and learn more. Also, listener, if you're watching this, you're probably seeing it on YouTube. Hit the subscribe button and make sure that you get brought up to date every time a new episode comes out. Obviously, we have this available anywhere you download your podcast as well. Josh, I want to thank you so much for joining me today. And I look forward to seeing how Wingman continues to dominate the market going forward. Yeah, no, I appreciate you having me, Brian. It's been great. Thanks very much. You bet.