Law firms are a vertical that can be incredibly profitable for MSPs. If you want more lawyers as clients for your MSP, here’s everything you need to know. Also this week, why MSPs are working so hard, and how MSPs are losing revenue.
Welcome to Episode 323 of the MSP Marketing Podcast with me, Paul Green, powered by the MSP Marketing Edge.
If you want more lawyers as clients for your MSP, here’s everything you need to know. Let’s talk about what lawyers look for in a new MSP, why they would switch, and what kind of marketing is going to grab their attention and convince them to talk to you.
So law firms are a vertical that can be incredibly profitable for MSPs. And I know that sometimes lawyers can be difficult people to deal with, but if you’re confident in your service and you know that you want more professional firms that put technology at the heart of everything they do, let’s get more lawyers. In fact, I believe they’re one of the easiest verticals to market to when you know what they care about. And spoiler alert, it’s not Windows 11 and Copilot.
Law firms buy IT differently from most other businesses. And the reason for this is simple. Everything they do revolves around risk.
Their risk, their client’s risk, the risk of regulators breathing down their necks, and the risk of missing a deadline because Outlook decided today was a fun day not to work properly. So if you want to win lawyers, you don’t sell IT support, you sell risk reduction and professional reputation protection.
Let’s talk about their biggest pain points. So first is compliance and confidentiality. Lawyers live in a world where one email sent to the wrong person can cause a catastrophe. So talk to them about secure communication systems, email encryption, MFA everywhere, data loss prevention, and of course audit trails. Second, billable time. Every minute a lawyer can’t work is literally money disappearing. So your message here is simple. We keep your fee earners earning. And then third, case management and workflow tools. Many firms still use clunky old systems or they haven’t fully adopted cloud tools yet. So show them how better tech can make caseloads smoother, faster, and more profitable.
If you want your MSP to stand out, you need to stop sounding like an IT company and start sounding like someone who understands legal practices. Use their terminology – fee earners, case files, discovery, retainers, compliance obligations, client confidentiality – all words like that. Because when they hear their own world reflected back at them by a potential IT partner, they immediately think, “Ah, yeah, this one understands us.”
You do need some specialised proof. Law firms don’t buy from generalists, they buy from specialists. So create a case study with a local legal firm, a landing page dedicated to IT for law firms with a short guide called something like, The seven biggest cyber risks facing law firms in 2026. And then just get a few testimonial quotes from partners or office managers. You don’t need dozens, one or two strong quotes will carry huge weight.
And here’s a little marketing trick. Law firms love audit. I mean audits is basically their favourite word. So offer them something like a free 20-minute legal IT risk assessment saying something like, Is your firm compliant with your regulators cyber guidance? Find out. And this positions you as a safety first expert rather than just another IT fixer.
Another smart tactic is to pick a sub niche. So don’t just market to all law firms, pick a slice. It could be family law or conveyancers or criminal defence or corporate commercial, maybe personal injury. Each of them has slightly different pressures and workflows, and the more specific you’re messaging, the more magnetic it becomes.
Finally, turn up to where lawyers are already gathering because you want to be in their world. So local law societies, legal breakfasts, CPD events, partner level networking groups, maybe conveyancing or legal tech conferences, lawyer of the year, dinner sponsorships. I mean, you could even do print newsletters for legal practices. We give a great printed newsletter every month to the members of our MSP Marketing Edge, and this is a great usage example for that. Basically, if you show up where they are, you instantly stand out because most MSPs never, ever bother to do this and certainly not within a specific vertical.
Lawyers are one of the most stable, recession-proof, time-sensitive verticals out there. And when you get one lawyer, you’ll get two, three, or four referrals because the legal community is very tightly knit. So remember, talk about risk, talk about reputation, talk about billable hours and position yourself as the specialist who understands the legal world better than any other MSP they’ve ever met. Do this and you won’t just get one law firm, you’ll become the IT provider for legal practices across your area.
MSPs, why are you working so hard? That’s a serious question because I know that you work so many hours and you barely take any vacations or holidays. And I know that you’re not scared of hard work to build your business. But have you remembered why you’re doing this, why you started the business in the first place? That’s the question I want to ask you right now. What’s your why?
But first, let’s return to why are you still working so hard? Why are you working 60 hour weeks to run and grow your MSP? Because you’re not just doing it for fun, right? I know that after about 50 hours of work in a week, it really does stop being fun. And I know that you’re not doing this to make yourself rich because there are very few MSPs motivated by having a yacht. Yeah, it would be nice, but none of us really are motivated by that.
What is it that actually drives you? Why do you do this, week after week? Do you know or are you caught in the trap of working hard just because you’ve always worked hard?
Let me share a little bit of my backstory to see if it’s anything like yours. So I started my first business 21 years ago after finishing a 13 year career as a journalist and a radio presenter. And at first, I didn’t mind the 80 hour weeks to get the business going and I really was working 80 hours a week on average. But as I added staff and as I fought for every little bit of revenue, I began to resent working so hard all the time for so little personal income. Does this sound familiar?
Everything changed with the birth of Samm, my only child. She’s now 15, she’s going to be 16 later this year. But back in 2010 when she was born, I quickly realised that I was trapped in my business and I couldn’t keep working at that pace while also being a present partner and present parent. So I made a decision. I was going to get good at marketing to get the business to give me the lifestyle I wanted. And of course, it didn’t happen overnight. I just found 90 minutes every day to start learning and experimenting.
My goal was an easy system to generate leads, qualify them as prospects, and get them into a sales meeting. My marketing got better and better, and I reinvented the business, turning it from being a struggling PR firm into a successful healthcare marketing agency. And actually I built that up and eventually sold it in 2016, which is when I entered the channel and started working with MSPs.
So back to today. Today I have a great work-life balance, but that’s by design. I work around 30 hours a week, which keeps me challenged, involved in my business, and able to drive growth. But I also spend plenty of time with Samm and with my partner. So my why is to spend plenty of quality time with the people that I love doing the things that we all enjoy doing. And that’s why I work every day. And of course I do it for fun and for the challenge as well. But the real driving factor for me is to give me a specific lifestyle.
I want to make sure that Samm can do all the things that she wants to do as she gets closer to being an adult and entering professional training. I have the time and cash now to do some serious travelling when that happens, when she’s a bit more independent, but I can also continue to be a present partner and a present parent every single day. I mean, that’s really important to me. It’s a core value right inside me. So let me ask you again. Having reflected on all of that, what’s your why?
Featured guest: Kim Simmonds is a dual-qualified lawyer in the US and UK and the founder of Cloud Contracts 365 and Law 365. With a passion for simplifying legal complexities and driving innovation, Kim has built a career at the intersection of law and technology. Through Cloud Contracts 365, she has developed a cutting-edge SaaS platform that enables technology businesses to manage their contracts effortlessly, offering AI-powered tools for contract creation, risk analysis, and management. At Law 365, Kim leads a team of legal experts dedicated to providing tailored legal services that help businesses grow with confidence.
I wonder if you have the problem of leaky revenue in your MSP. This is the money your business should be earning, but it isn’t because it’s quietly slipping away through avoidable gaps. For an MSP, leaky revenue usually shows up in places like unbilled work, perhaps engineers doing quick favours that never make it onto an invoice, scope creep in fixed fee contracts, under price services that haven’t been reviewed in years, and missed renewals for licenses, support, or security tools.
My special guest today is an expert at spotting everywhere that your business is losing money and making sure you stop every leak.
My name is Kim Simmonds. I’m the CEO and founder of Cloud Contracts 365.
And it’s so lovely to have you on the show, Kim. Now, you are obviously a lawyer based in the UK, but I know that you’re going to give us plenty of advice today that MSPs all over the world can use. So it’s not going to be specific legal advice, but it is going to be talking about how MSPs can stop something called leaky revenue. What is leaky revenue? You and I are going to dive into that in a couple of seconds.
Let’s just, first of all, find out a little bit about you. So have you always worked as a lawyer within tech or is this something you’ve only been in recent years?
Yeah. So for my sins, I have only worked in tech pretty much the longevity of my career as a lawyer. I say that, it’s been an absolute fantastic journey. So I’ve been a lawyer for over 20 years. 15 years has been dedicated to the MSP community, the MSSP community. So I know this community like the back of my hand, safe to say.
That’s awesome. That’s great. In fact, you know this community better than I do because I’ve only ratcheted up nine years. It’s almost like a comparison thing here. Who’s done the most number of years? Maybe it’s kind of like being an MSP jail or something like that. So the kind of work you do with MSPs, it is around this concept, I know you do lots of different things, but a lot of it is around this concept of “leaky revenue”. This was a term that you actually introduced me to, and I thought it was such a cool term. When we talk about leaky revenue, what do you mean by that?
Yeah, it’s such a great question, Paul. So as a lawyer, I’m always looking at the contracts that these MSPs have in place for their customers. And ultimately, as a lawyer, we have to always think about how are we going to protect the business? And when you’re thinking about protecting the businesses, not just looking at things like data protection and liability, these are really important things in a contract, but it’s looking at the everyday issues that MSPs face and how can you mitigate their risk. So looking at that, what are the everyday kind of leaks as I put them in their revenue? And it’s really interesting because when you start to look at it from that side and not just the legal side, but the commercial side, the lawyers actually can do a fantastic job at making sure those contracts are far more watertight than sort of generic templates out there.
So are we talking about loopholes that allow clients to walk away from contracts or can you sort of dive more into where the revenue would leak out through a bad contract?
Yeah, absolutely. So it spans across multiple things. Let’s look at things like the term. A lot of MSPs they come to me and they say, No, we’re used to doing 30 day rolling terms, right? And I’m like, Okay, but how does that coordinate when you’re selling NCE licensing? Because you’re going to have to commit them and you have to provide support with their licensing. So if they can then leave your services, but you have to keep them onto the licensing, how’s that going to reflect in your contracts? But also from a valuation point of view, if you’ve got a 30 day rolling terms, already that’s revenue, sort of that’s valuation out of the business because someone who wants to go and buy or take over the business later on wants to have a more steady income stream. So that’s number one.
Looking at the termination rights, let’s say some MSPs are willing to do the 12 month minimum term with automatic renewals, that’s great, but have you paid attention to when you’re giving them the clients the right to terminate that contract? It shouldn’t be 90 days at any time. It should be 90 days, for example, to terminate at the end of the term or the renewal term.
So it’s looking at terms, it’s looking at termination rights, it’s looking at price increases as well, because this happens all the time, especially on a renewal.
MSPs, firstly, they don’t pay attention to renewals. So our tool actually helps them to pay attention to the renewals. It reminds them when they’re coming up, but on top of that, they can then do a price increase. I have so many MSPs who come to me and say, I’ve had a customer for 10 years who’s never had a price increase. And I’ve just swallowed up the profitability of that. I’ve taken the hit myself. And I’m like, why would you do that? Well, we haven’t bothered to put the right terms in the contracts. I don’t want to rock the boat. You absolutely have to rock the boat.
These are not the customers you need to keep on and your contracts have got to show your way of doing things. So price increases such as RPI or CPI, being able to give third party increases at any point that that third party increases to you, and of course then getting consent if you’re increasing above RPI, but always having that inflationary rate in your contracts, you don’t have to get consent, you just lift up the price every year. So there’s a lot more, by the way Paul, I just don’t want to keep on talking, but I love this subject so much.
No, absolutely. Please keep talking, Kim, because one of the many interesting things that you talked about there was price increases. And you and I, I’m sure both know MSPs, some of whom are on top of price increases and do them every year religiously. But it was really interesting for me to hear about the MSPs that don’t do price increases religiously, and therefore they are losing out on that profitability. So tell us some of the other ways that you can lose revenue out of your MSP without realising it.
Yeah, that’s a great question, Paul, thank you so much. In other senses, price increase is one thing. NCE terms, they neglect to put the right NCE terms, which is committing the client to that 12 monthly term. That’s something that happens quite often, and so there’s no contract right to keep them in. There’s another thing here that’s really important, and it’s a bit of a sensitive one. It’s around the termination suspension of the services right. Here’s why.
Often you’ll get a client who’s missed a payment, or they’re about to miss a payment, or they’ve been bad payers all the way through. And the accounts team kind of know it, but there isn’t really a contract term to support an MSP to say, Hey guys, you know what? This is getting too much now. We need to suspend the services. We need to terminate the services. This is too much for us now. And the problem is this, if it’s found that that particular customer goes insolvent, what the MSP is not understanding is that they are considered in the central supply of services under the Insolvency Act here in the UK, which means they can’t turn them off at the point of insolvency, but they can turn them off before they are aware of the Insolvency Act.
I cannot tell you this past year, how many people have been subjected to insolvent businesses is terrible right now. And this is them having to take the hit of those licenses themselves and have to pay their distributor or Microsoft if they’re going direct because their distributor doesn’t care. They’re committed to 12 months, they have to pay for those licenses. So it’s really things like that. You’ve got to get that right in your contracts, but also in your processes.
I mean, that sounds like a nightmare scenario, having to pay for licenses on the behalf of a customer that isn’t even paying you anymore. But let’s broaden this back out to all MSPs around the world. Do you typically see when you’re working with MSPs that at the point they get serious about contract and getting all the legal terms and all of that right, that’s the point that really rapid growth happens within the business because they’re just sort of taking away the winging it approach, they’re making it up as we go a long approach and they’re getting serious about every aspect of their business. Is that what you see?
Absolutely. When MSPs understand that their operational excellence includes fantastic contracts that protect the business, that’s when they start to see the growth trajectory, 100%. Because they have cottoned on to a few things. Number one, the client base that they have and the type of clients that they need, and that’s really important. And when they start to professionalise like that, when they start to, and I hate to use the word, but grow up a little bit in that sense, they’re realising that the people that they’re now selling into are far more operationally aware of business than what they’re used to. And when their clients are needing that operational excellence from them, having poor contracts to put in front of the customer is like losing one of your three halos.
I call this the halo effect, the losing the halo effect. I don’t know if you know about this, Paul, but typically people have three halos when they start a new relationship with a customer. And if you lose three halos, so three things that you do wrong, that’s when people start to really question whether they’ve got the right supplier in place. Why lose your halo on poor contracts when you probably need to save that halo for poor delivery if something like that happens or a missed P1 ticket? Save it for those things that really matter in your business and get the basics right.
I love that. And no, I hadn’t heard of that three halos concept before, but that’s an idea I’m going to pinch. So thank you very much for that. Kim, you’ve been wonderful to talk to. Thank you so much. Just tell us a little bit about what you do to help MSPs. You mentioned earlier that you have a tool. So tell us about that tool and what’s the best way to get in touch with you.
Yeah, absolutely. Thank you so much, Paul. And yeah, that three halo, I absolutely love it. I do a lot of customer journey workshops with my MSPs to kind of teach them how to get the client on board and onboarded really smoothly with great contracts and processes. So it’s a good one to use for sure.
My tool is called Cloud Contracts 365. It’s designed just for MSPs and allows MSPs to go and create those fit for purpose templates. It’s got all the things that I just mentioned, NCE, all the termination rights, everything to protect their business. It’s a lot cheaper than going to a law firm and to lawyers, and they can create it. They can also review contracts. So if they’ve got vendor contracts, they can review. There’s an AI tool in the platform that will basically show them what legal risk there is and what to do about it.
And they can manage the contracts, e-signatures through to automatic renewal reminders. And we have an integration to Halo PSA as well. So really helps them to kind of manage the quotation to contract link as well there. So my address is www.cloudcontracts365.com. And my email is [email protected].
Hey, this is Brian Gillette from the FeelGood MSP, and here is my marketing idea. You should go and pull the transcripts or call recordings of your last 10 sales presentations. If you’re using an AI tool this should be very simple. What you’re going to do is you’re going to use the AI tool or your transcript to find every objection that your prospects listed, whatever reasons that they might not want to hire an MSP or concerns about hiring an MSP, whether or not you won that deal.
Make a bulleted list of them and then you’re going to start writing a weekly blog post where the title of the blog post includes that objection, but reversing it. For example, if the objection was, “Well, we’re worried about losing control by outsourcing IT instead of having it in- house.” You might have a blog post that says, “Why having an outsourced IT company will give you way more control than an employee.”
Just go through that list. You can use AI to help you support it, or you can even use those talk tracks from the transcripts of how you handle it in the sales call, and that’s going to make your marketing much more visceral, much more relevant to your audience.
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