Feel Good Close on YouTube (includes podcast episodes)

The MSP Sales Podcast

James Steel (00:00)
Hey, I'm here with Brian Gillette, founder of Feel Good MSP and host of the MSP Sells podcast. Go and check it out. Brian has helped so many MSPs with remarkable growth through his empathetic approach as a differentiator. So I am absolutely thrilled to have you on the show Brian to chat to us today. How are you doing?

Brian Gillette (00:19)
I'm doing fantastic. I've been really looking forward to this.

James Steel (00:22)
Listen, you carved out something of a something of a reputation attract record for really helping people mostly I'd say with sort of net new business acquisition Is that fair to say?

Brian Gillette (00:31)
Yeah, that's definitely my area of focus for sure.

James Steel (00:34)
Obviously on the Harvest podcast,

we're keen to look at how we can sort of look within our existing client base, any potential there. So I've got to throw it over to you. In terms of where that potential lies for you, when you're working with clients, what are your first steps where you think, actually, look, there's loads of potential there in this particular area. Where do you see gains when you're working with?

Brian Gillette (00:54)
Well, I'm going to say, let me open my first controversial thing that everybody's going to disagree with me on, which is that I think account management or I'll say that finding revenue inside of your existing client base is like 10 times easier than finding cold new revenue from the streets. It's just an easier job. I don't mean to say that it's guaranteed that you'll find new revenue.

But in some ways it is, if you just have some basic practices in place, it's pretty inevitable that you could just keep finding more opportunities to create value for that client.

if I can say it clinically, if I'm looking for new ways to inject MRR and one-time revenue into my existing client base, I want to make sure that I'm injecting the right MRR rather than just whatever MRR they'll pay me. Because oftentimes people will start spreading out their focus because they go for the land and expand approach and all of a sudden, if you're not careful, you're doing things that are way, that you shouldn't be doing just because somebody asked, hey, by the way, do you do websites? And you go, sure.

Do you do SEO? Fine. And you know what I mean? You just start adding more services simply because people ask for it. So I think it's important that you remember, as long as you stay really vigilant, you stay focused, and you know what it is that you wanna do and spend your energy on, that revenue can be found in your client base. Don't just take whatever dollars people are willing to pay you because that could end up really spreading you quite thin.

James Steel (02:00)
Mmm.

Brian Gillette (02:20)
and make it much more difficult to sustain and scale that as you start bringing on that new logos in the future.

James Steel (02:26)
And so when you're looking then at the potential in a base, where does most of that come from? Is it generally new service revenue, do you think? Is that where you see it or are there other areas?

Brian Gillette (02:35)
mean, it's a good question. think you kind of have to go to the data and it depends on who your average client is. If you have like 10 seat.

Clients versus hundred seat clients then you're you're going to be finding and searching for different opportunities I think the starting point I'm sure that many of your guests have approached this and I don't know I've never had a very Sophisticated technical stack in order to help me do this But we basically just spreadsheet it out all of our clients what's in their stack or what are they paying us for? What's going well? And so we would look at like

What investments have we made on the stack per client? We break them down in columns and then we start looking at tickets per user was the status, the stat that we use internally to just feel like we should see a direct correlation of like the bet, the more we've invested energy into them, the less tickets we should be getting per user per month because things should be getting easier and easier. And so when we see, when we saw somebody who had a really high TPU or some people call it a ticket utilization rate,

then that's gonna be the flag where I look in and go, why is this client so squeaky? that's an area where we can actually provide better value.

And it's obviously an area where they probably aren't leveraging everything that we can do for them. So that's the first symbiotic place I'm going to look for new revenue is like, where can it actually make the most impact? Not just who has some dollars that I can take from them. I think that you have to use the data to tell you.

Are these projects or this is this out of date hardware? this all like low end, low grade hardware that's really troublesome? And so can I make an actual business case for them to show them, Hey, look at how many problems you have because you insisted on buying all this ubiquity access points. So nobody can never access anything. I can actually show you why those ubiquity access points were so cheap. Look at the data. things are not well because you bought the cheap route. I think we have to have a serious conversation.

your

customer about your goals and figure out where on the spectrum you want to be on cost versus risk basically we need to buy something better so that you have a better quality experience better service.

James Steel (04:33)
Yeah,

that's really good. I've not heard that talked about quite like that. So actually using the TPU as a metric, is that something do you find most MSPs have that? that a common one that's frequently available? Is that something you recommend that should be in place?

Brian Gillette (04:45)
I don't, yeah,

I don't, it's a good question. the real answer is I don't know if people use it or not.

I can't imagine why you would not want to use that information, especially if you've got thousands of users, like who's calling you? Why are they calling you versus the people who aren't calling you? And are there trends that we can find in the actual tickets? Right. Cause your tickets are like, it's that's gold. That's liquid gold. That information is super valuable. What are the friction points in this experience? And our, our whole promise as an MSP is to become more proactive, which means we need to use that as evidence to start. We need to start getting ahead of

those tickets. So the truth is a good MSP should be getting less tickets over time if they're really doing their job

James Steel (05:26)
if I had a PSA or help desk system full of ticket information, that would be straight into AI. And I'm sure this is happening a lot, but straight into AI to try and analyze, because we're always looking at ways we can help with sort of business process improvements and ways we can spot pains in our clients. And it's all sat right there. They're offering you up front and center, aren't they?

Brian Gillette (05:42)
Yeah, right.

And yeah, and

you're absolutely right. There's tons of new cool tools that are coming out. But I would even say, especially to, you know, a million dollar MSP, two million dollar MSP, like don't, don't go spend 50 grand on a super power BI automation. Just go, just look at the tickets. Just look at them and go, all of these are about email or all of these are about wifi. Like this is good. You know what I mean? At least infer what you can do something with the information. Don't do nothing.

I think the secret here is that what I have observed is MSPs feel like they have to fall in one of two camps where they either have to like, how do I make as much money as I can off of these clients? Or how do I bend over backwards to be as helpful as I possibly can so they never leave me? Am I? Yeah.

James Steel (06:28)
That's so true. There's got to be a balance, right? I feel that exact

same thing. mean, yeah, we work with this idea of white space and so on. And that inherently is like, how many services can you fit into a customer base?

Brian Gillette (06:38)
if your business is set up correctly, why are those two things, why is that an either or?

Why can't you make more money by creating more value? That's the whole freaking point of your business. you've got to change the way you're thinking that this is not, this is not adversarial. It's not like, Hey, I win by getting more money out of my clients. And you might not be consciously thinking that, but your behavior infers that when you be, when you think adversarially about like, I got to wait for the right moment and twist the knife, or I got to try to expose whatever, you know what I mean?

becomes very combative. that's a sign that you you've got a real mindset issue that's making it harder for you to make more money.

James Steel (07:16)
So I'm really interested. you're, a lot of what you talk about is an empathetic approach. So applying this empathetic approach to more of a account management essentially, how can we use that approach to better have conversations with clients about these things that need addressing, to take out this combative kind of stance?

Brian Gillette (07:35)
I'd say sort of start infusing your business, your outcome and pain conversations with just more regular human interaction. The sort of the first level of marketing and sales that people start to get into is you have to stop talking about services and you have to start talking about outcomes.

And everybody's heard that talk track because that's of literally marketing 101. Like that's the most simple transition to become a marketer is like tell people what they get by working with you. And of course, marketing also applies to internal, like account-based marketing and internal marketing is just as relevant as outside prospecting marketing. You have to market and create narratives and create awareness for your internal clients. but instead of going to your, to your, in your QBRs or whatever your touch points are and saying like,

Hey, what pains are you having or what business outcomes can I help you with? Just start having real curious conversations. Like how has it been working with us? Tell me more about what you do again, Sally. You do this. Okay. What does that mean? Things change a lot. What does it mean to be a secretary in 2025? What kind of stuff are you interacting with every day?

And out of curiosity, you feel like there's, do you feel like you're getting things dumped on you that other people just don't want to do? These are all basic human conversations. And each of those is going to give me really valuable data that I could potentially use to find opportunities to inject more revenue and improve Sally's quality of life.

I just took the textbook questions about give me all of your pains and values and like, you know, your aspiring business values and just make it normal.

James Steel (09:07)
Is your advice to sort do this with multiple stakeholders or how do you approach that sort of becoming really sort of entrenched in an account and building that sort of the best relationship that you can?

Brian Gillette (09:06)
Yeah.

Yeah, that's a really good question. In pre-sales, there's the concept of multi-threading.

multi-threading, to oversimplify the term, just means when you're trying to do a sale into a large client, you want to build contacts and relationships with multiple people inside of the org instead of just having one so that you can get different perspectives and potentially get like you can get a more well-rounded understanding of their need and basically get more ways in to the organization. So I think it's just as relevant in account-based marketing. You shouldn't, yeah.

world you have relationships with more than just one person but you do have to balance that with what in again in pre-sales we would call the sales champion so you have one person in the org who you who is championing your relationship but you would never want the entire relationship equity to live on one person who's prone to turn over and go to another organization I would say if you want to build a deep deep deep relationship with somebody it needs to be at somebody who has lower risk of turning over so that's probably

at the executive level. If you don't have a key executive relationship, then it's a good idea to build more than one. So you're de-risking the chance that your whole relationship is going to walk out the door one day.

If you want to be a real strategic partner long-term, I do sort of think that your organization has to have relationships at every level of your client. Especially if you're targeting larger clients, I would say 50, 75 users or above. The end users should know who you are. The middle management should know who you are and the executives should know who you are. But each of their relationship with your company is different. So if you're an account-based manager, an account manager's job isn't to build a relationship with every end user. That's the support front lines job.

So I think leveraging the rest of your MSPs, the rest of the MSP team.

to sort of create multi-level relationships inside of those organizations and then even training all of them to have their ears to the ground to look for opportunities where we can better serve them.

That's the whole MSP's job to make sure that they renew.

James Steel (11:13)
I really like that. There seems like this huge potential in

cross-functional relationship, but it's often quite hard to actually put into practice and get happening regularly and get everyone bought in, isn't it? I don't know if you have any words of advice around that, how you go about doing that and making sure it actually happens.

Brian Gillette (11:28)
you're 100 % right. think it has to stem from the culture of your MSP. You have to make a core decision in your organization's DNA. Like, what kind of company are we? And I'm very fond of saying a good MSP is not in the IT business. They're in the customer service business.

that's what your job is. Take care of your customers. That means every single layer of the organization, your CEO, your VC, so your technical manager, account managers, your account executives, your BDRs, your tier one techs, your tier two techs, they're all customer service. So when somebody calls you with a problem,

If you remember, my job is to take care of this person, not to just reset their password. My job is to take care of this person and how the permutation of that in this interaction is an email password reset. To me, that is a font of never ending patience for frustrating people when you remember your job is to make them feel good and take care of them. So you have to decide that's our role in this company, in our clients' experience, our role is to take care

of them and if that starts at the top, it's much easier to disseminate culturally and then to actually hold people accountable to do it.

So if you're struggling with that disconnect, that's the DNA you have to sort of iron out on the organizational level. there's probably tons of practical advice, even in this show, just listen to all the episodes of Harvest and there's going to be tons and tons of little tips and tricks you can do

But I think that's important to remember that the practical tactical tips don't really mean anything if your culture is going to betray them all.

James Steel (13:04)
And the thing is, even if it's not, I mean, you would hope it comes from a good place, but also you need to think it's good business sense, isn't it? Not only to be looking after your customers well, if you've got that relationship, then you're gonna be seeing so many more opportunities off the back of it and retention will be good and so on. So yeah, it makes a lot of sense.

Brian Gillette (13:16)
Yeah, exactly.

And again, those don't have to be mutually exclusive. That's the whole point to me.

of an empathetic approach means why is it that I have to win or you get to win? Like, why can't it be that we should align our entire business value and mission and product in such a way where when we win, the client wins and when the client wins, we win. It's not just that it's the right thing to do morally, ethically, relation wise or otherwise, it's also the right thing to do financially.

Because that's going to keep your organization strong and resilient and recession proof and retention, high, high retentions because people actually like working with you.

James Steel (13:53)
Brian, I'm so curious. Can you give us, I mean, you don't have to reveal any names, but can you give us any sort of theoretical examples of those that maybe come in and not such a good place and then perhaps have got to a much better place when it comes to sort of making more revenue or just doing better within their existing customer base?

Brian Gillette (14:08)
I'll start with my MSP.

we were so focused on new business and we always did a good job. It's not like we didn't care about our customers, but we just hadn't yet systemized account management and real customer care the way that we had systemized new logo acquisition. And so we had a few customers, we didn't have a ton of loss because it's so hard to leave an MSP. Like you can be a crappy MSP for a long time before they leave. And yeah.

James Steel (14:33)
Which is another reason it's so difficult to do new business acquisition, isn't it?

Brian Gillette (14:36)
Exactly. Because it's just so hard to leave. Right. And not to say again, we weren't a crappy MSP, but what I did was I took there was a front end sales guy. He had made cold calls for a long time and he sort of burned out. And we just moved him over to account manager. We're like, your job is to run QBRs, which I thought I invented, by the way. I call them QSRs. And I was like, I have this great idea for what, how we can take care of clients, come to find out there's like huge SaaS companies that have just built their whole career on just running QBRs. Right. But

That was a really big piece of what we did was pivoting over to like, just take care of these people and answer their questions. It kind of become a point of contact for all things relationship outside of just support tickets. And my account manager had a non-recurring revenue and a recurring revenue quota every month. So he had to deliver new MRR and he did.

It was something like 12 to 15,000 MRR a year he brought in, in new business, just from QBRs.

So that was really critical. Another organization I've seen do this really well was this really, really great MSP out of Florida. They're all marketing based. They have like six people on their marketing team and they say none on their sales team. Obviously that is their sales team, but he told me the story of he was on site at a client and his point of contact, she was kind of crabby and she hadn't really won her over yet. he saw, there was a mini fridge in her office and her garbage can had two or three empty

monster energy drink cans in it. So he was on site and a technician was coming to like bring some cable they needed and he texted the tech and said buy go buy like three monster energy drinks and they just restocked. I know I know but he restocked her fridge and I'm like dude it's kind of an absurd example.

James Steel (15:57)
Okay.

That's not good advice for anyone, Brian.

Brian Gillette (16:15)
the reason I share that example, I'm not telling you, go buy everybody Monster Energy drinks. Never buy me a Monster Energy drink, please. Yeah, yeah. But the point is that he was there, he had eyes to see what she needed, not eyes to see what the technical problem was.

James Steel (16:20)
I get the sentiment, don't worry.

Brian Gillette (16:32)
He sort of chose to kill her with kindness because remember she was not, she wasn't really even pleasant. It's not like, I love this person. So I'm, I'm being more mindful of her. He was like, how do I, how do I show her that we're on her team? I thought that was a really interesting example of nothing else, an anecdote to keep in mind.

I'm not telling you that you could have to do whatever they need or that you have to cross any boundaries that aren't sustainable for you.

And other than that, the last example I'll give is like, you know, had a guy came through one of my workshops. I have like a $50 workshop was just high level advice. basically said he had ad hoc sold different parts of his stack to different clients. Cause he was trying to like win every single sale. He was trying to get people to pay an extra five bucks a seat so he could add whatever dumb feature here. And which are tons of MSPs do this. They sell one single license at a time.

but that's what this guy was doing. And so he had different tiers. had all this, like everything was sort of ad hoc. So I said, make a spreadsheet of red X's and green check marks and go all the way through until it's all green. And if you can't get a client over 70 % green, fire them.

And so he did, and he just made it all green. He lost like 30 % of his clients and his revenue or his profit went up like

Less work, way more money simply because he just a simple spreadsheet. There was no AI involved. He just, he just did it the hard way and he got his ducks in a row. He got it sorted

James Steel (17:48)
Yeah.

Brian Gillette (17:52)
He became he became very vigilant about what we were willing to do and not willing to do instead of what the client was willing to say yes to the first time that was no longer his standard for what he sold his standard for what he sold was now unflinching and that gave him a lot more confidence even in the in the upfront sale and in the account renewal to be like hey you don't have email security we're not comfortable with that so you've already signed a waiver of liability but I know how this story goes you're gonna blame me when you guys get hacked so that's not happening here's the new price if you want me to

to manage you, this is what it costs.

James Steel (18:25)
This is a definite theme,

this confidence in an MSP, even the best performing MSPs, having that confidence, either better ones, even bordering on arrogance sometimes, of sticking to your pricing, sticking to your packaging, it really seems to bode well. I guess we wouldn't know because the ones that it didn't work for might be out of business, but the ones I speak to, certainly, it seems to be something that really, really works well.

Brian Gillette (18:43)
Yeah.

Yeah, yeah, big time.

James Steel (18:47)
Listen, we had a quick chat about sort of how to approach things like hardware refreshes. That could be a nice area potentially. I mean, I don't know, there's not obviously a lot of margin in hardware these days, where would you say the money is and where's the opportunity there in hardware? Is there anything you can, any advice you can offer around that?

Brian Gillette (18:54)
yeah.

Yeah.

I won't go on a tangent about certified refurb gear because I'm a big fan of using certified refurb because you can get a lot more margin as long as you're clear that you're using refurb gear. Don't try to pass it off as right off the factory line. I would say for hardware refreshes, the real money is in managing your TPU.

James Steel (19:13)
Yeah.

Brian Gillette (19:22)
and de-risking your clients. for example, in my business, we learned by just looking at the data, when a computer's over five years old, was was like considerably more likely to have a hard drive or power supply failure. we don't want a critical ticket where somebody has to stop what they're doing and drive to an office and plug in a new computer or swap out a power supply. It cuts everything to a grinding halt and the client is not happy no matter how good of a job you do.

because they still had that disruption.

So we're like, we've got to get new computers in before they die, period. we just use the data to know how old is this computer when it's four and a half years old, I always tell people send an email out says happy birthday in the subject line. The body says happy birthday to computer. It's about to turn five in human years. That's kindergarten and computer years is going into the old folks home. Push, just push this button. I'll schedule 10 minutes with you. We'll get it swapped out for a new one. So hardware is not just about the project. It's a look at the, the tail.

James Steel (20:05)
I love that.

Brian Gillette (20:15)
the long tail value of having a lower of de-risking the chance of a critical ticket, the chance of an outage and de-risking the chance of user frustration So your TPU should be going down over time. Your risk inside of those organizations is going down over time. And of course you can make a few bucks in the process of putting those things in.

James Steel (20:35)
Brian, it's that time in our chat for our typical industry segment, which is industry manure. Now this is your opportunity to let us know what you think is a crock of shit. I know you're looking forward to this one, because I've got a feeling you've got a few ideas. What do you see is not always fully true in the advice that you hear banded around in the MSP industry.

Brian Gillette (20:47)
you

Hmm.

James Steel (20:55)
So, so love.

Brian Gillette (20:56)
my goodness. Where the hell do I start James? No, I'll keep it simple. I will say that the biggest crock of shit is that a one of the vendors in your stack should be talking to your customers. Never in a billion years would I let my backup provider try to sell backup to my end users. It's a massive, massive mistake.

James Steel (21:10)
Okay.

Brian Gillette (21:19)
Because they want to do it because they want to sell agents. They can't sell it direct, which is why they went channel, because nobody cares about their product. So they're going channel and they're trying to just beat you over the head with why all the reasons why you should add it and create new MRR and get more margin. Then you just take everything they say, you regurgitate it to your end user and they go, what are you talking about?

No, I don't want to harden my end point for, what are you talking? I don't know that means. Who cares? It's a pass through of a bunch of narrative that will never be relevant to your client. what ends up happening is you start fragmenting the perceived value of you as a manager, because now you're letting all of the nonsense.

James Steel (21:41)
Yeah

Brian Gillette (21:58)
That is everything the MSP has to be aware of is now going to the end user and you're asking them to make a decision for you about what you should do to manage them. It's a massive mistake. Never let one of these vendors talk to one of your clients. They don't know how to sell managed services. They know how to sell their dumb little tool, but they don't know how to couch it inside of the whole relationship narrative, which is that our job is to de-risk your organization, be your technical partner, blah, blah, blah.

And then you end up becoming an itemized commodity when they start seeing between the seeing all the seams and looking behind the curtain and realizing that you're really just a var.

they'll totally change their perception of you. D risks, it devalues your authority completely in my opinion. And frankly, it's just not going to make you more money.

James Steel (22:43)
and breathe. It's all out. That's a great one. I love that. I love that. That really, really sound advice. It goes against everything, doesn't it? That we're working towards. So it makes absolute sense. Our final segment is called Pass the Pitchfork. So this is where we get a question from our last guest. So this is from Maria Armstrong, who is the head of Academy at PAXA APAC.

Brian Gillette (22:45)
thanks for letting me get that off my chest doctor. That one was eating away at me.

Okay.

James Steel (23:10)
And she was interested to know what your take was on where AI sits within the sales process, the modern sales process for MSPs. Is there a place for it in your opinion?

Brian Gillette (23:21)
I got a spicy take for you. think AI is way less important than people are trying to get you to believe Like it's not even funny. Like by an order of magnitude, it's less important than they want you to believe in the sales motion. AI is great for what it's great for.

I don't know what the definition is. Clay.com AI is a data enrichment considered AI now? Fine. Let it enrich your data and scrub for people's email addresses. But if you don't know how to talk to a human being and explain to them your product, your product should not exist.

Every MSP has, they think that's their value prop as they go. Well, what makes us different is that we actually care about our customers. And then they're hiring AI agents to go and peddle their nonsense to the, to the end user. It's just not that important. If you had five real conversations a day and you are super clear and you had your sales process down, you're going to smoke everybody who's trying to use AI to send 10,000 DMs a week.

Or a month, give me a break. If that stuff worked, then we would all be zillionaires. AI should be taking the role of a sales admin at best. Right? So updating your CRM, making sure that you're reconciling account information, those sorts of things that that makes a lot of sense. so a CRM admin or a sales admin AI should definitely be there. Um, AI should not be doing anything.

to help your client understand your value. That should be what a human being is doing. Because managed services is not like SaaS where the market, the TAM is super broad and everybody's always in a buying position. Your TAM is really narrow and people are only ever buying once every three years. So you're really gonna blow that conversation with a dumb AI generated thing when you could have just said it to them yourself. That's my opinion.

James Steel (25:04)
That's a great way to look at it. Yeah, so yes to behind the scenes, no to between you and your potential buyer. Brian, to end, do you have a question for our next guest who could be an MSP, could be an industry expert, can be any topic you like, something to put them on the spot. It's always fun.

Brian Gillette (25:09)
Mm-hmm. Yeah.

I have one, but it's a really hard one. Let's say this is a might be a doozy. Maybe it's easy for them, but here's the question. In the modern business, I'm going to use that term in the, the, in the next generation of business context where we're seeing work from anywhere, bring your own device, decentralized businesses. Why does a business like that need an MSP?

Why do I need an MSP I have 20 employees all over the world, bring your own device, no network, no centralized cloud. What does an MSP do for me that I really need?

James Steel (25:52)
question.

you want to do a quick yell from the barn? Let us know where we can find out more about you and dive into whatever's current for you at the moment. Obviously you need to give your podcaster shout.

Brian Gillette (26:00)
Sure.

Sure. Sure. Yeah. Well, MSP sales podcast.com another version of what we're sort of doing here. We really focus on the pre sales side of So if you like podcasts, then that's a great place to go. We got to have you on by the way, James, you got to come over. Yeah. And then of course, feelgoodmsp.com. We always have multiple feature events scheduled out and you can learn more about what we do for MSPs there.

James Steel (26:13)
That would be wonderful. Yeah, book me up.

Brilliant. Brian, it's been so good talking to you. Thank you so much for sharing your wisdom. We've got plenty of tactical actionable stuff out of that one, think, don't you think?

Brian Gillette (26:30)
Good, I hope so. That was as tactical as I know how to be. So I hope you can do something with it. Thanks, James, for having me. This was really cool.

James Steel (26:33)
Wonderful.

Yeah, don't worry. Listen, look after yourself. Thanks for being with us. Take care.

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