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Welcome to Episode 287 of the MSP Marketing Podcast with me, Paul Green. This week…

• Great marketing for Windows 10 end of life: There’s a hot new opportunity – Windows 10. This soon to be obsolete operating system is good for your MSP with this end of life marketing opportunity.


• Ask this cybersecurity question to speed past phone gatekeepers: Most MSPs really struggle to reach the person they want to speak to. This trick will help you get past the gatekeeper and start a much more productive conversation.


• Can you drive new revenue with DMARC?: DMARC isn’t just critical for ensuring messages reach people’s inboxes, my guest believes that DMARC can actually generate new leads and new revenue for your MSP.


• Paul’s Personal Peer Group: This week’s question is about getting more attention and engagement by adding personalised videos to emails. Find out which software options are available for this.

Great marketing for Windows 10 end of life

So you’re an MSP trying to find new clients and also increase revenue from your existing clients. Well tell me, have you heard about the hot new opportunity – Windows 10? Yeah, you heard that, right? But how could talking about an old, soon to be obsolete operating system be good for your MSP? Is this a credible way to win new clients or upsell your existing clients? Let’s find out about the Windows 10 end of life marketing opportunity.

Five months. That’s what we’ve got until Windows 10 reaches its end of life and it’s been with us a decade you know, it first launched in 2015. Will you be sad to see it go or are you already a big fan of Windows 11? Anyway, that’s kind of irrelevant to this conversation, and I know that loads of MSPs still miss XP. I’m kind of joking there, although do you?

But what we’re talking about here is using Windows 10 as a marketing opportunity, not only to win new clients but also to upsell your existing clients. You see anytime there’s a big enforced change in the marketplace, like a major operating system reaching its end of life, that creates an opportunity for you. And one of the key things in marketing is always putting yourself in the shoes of the person that you are trying to reach and influence.

For an ordinary business owner or manager, Windows 10 reaching its end of life is going to be a bit of a shock to them in October.

Not for you and me, they announced the 2025 end of life date four years ago can you believe. But what’s big in our world and surrounds us every day does not surround ordinary business owners and managers. And you and I both know that there will be many, many people running their businesses on Windows 10 with no idea that this is coming. And maybe their MSP or their break/fix outfit has told them, but they weren’t listening or they’ve ignored it and ignored it and ignored it, and then suddenly it’s October 2025 and it’s crept up on them.

So what’s the best way to tackle this for prospects and for existing clients? Well, let’s look at those separately. And the easiest way to start is with the prospects. Now, I’m guessing you as an MSP have a preferred route forward at this point, in terms of what to do after Windows 10. So many MSPs will want their clients to upgrade to Windows 11. I do know a few MSPs that are still trying to hang on to Windows 10, and let’s not get into a technical conversation about that because that’s not really what this podcast is for. But I guess for your existing clients who are still on Windows 10, their routes forward are either upgrading to Windows 11 or of course paying for the extended security updates.

I truly believe that as their MSP it’s down to you to educate them about their choice and the pros and cons of each one. Then give them a recommendation based on your relationship with them and what you think is going to be best for them. Now, this will be a great time to set up meetings with your existing clients to actually have that conversation. And there’s no point leaving it till September as suddenly everything becomes a rush and an emergency if they want to get off Windows 10 before it reaches end of life.

At this time of year with a roundabout five months to go, I would book yourself either Zooms or real life meetings with your existing clients to review how many devices they’ve got that are still running Windows 10. And obviously you’re going to know that in advance if you’re all over your asset management, but I would have that conversation with them now. And yes, that could generate some nice project work for you, but the bigger picture is that you are helping your client to stay ahead of the curve.

If they insist on staying with Windows 10 and paying for the extended security updates, as frustrating as that might be for you, that’s up to them. And I’m sure you have a very clear opinion about how that’s going to affect your relationship and the level of support that you’re able to offer to them in the next couple of years. But the key thing with any conversation like this that you are having with existing clients is about protecting the long-term relationship, and making sure that your client is happy and well protected so that they will still be with you in 10 years time. That’s the most important thing.

Let’s talk about using this change to win new clients. I believe it’s a similar opportunity in terms of educating people about the pros and cons. Although because you don’t have a working relationship yet with new clients, with people who are prospects today, you would go about it differently. So let me tell you what we’ve done in our MSP Marketing Edge service because that might give you some ideas.

We’ve put together a whole bunch of materials which we actually delivered to our members just a few days ago. And those materials are designed to help them catch the attention of leads and prospects and educate them about what’s happening and what the implications are of the end of life of Windows 10. So we put together a full educational guide. There’s a video, there’s a whole email sequence, there’s some social media content, there’s a postcard which can be sent out in the mail and a full direct mail and a multi-step follow-up sequence. That seems like a lot when you put it all together in one box like that, but my goal when putting this together with my team was to give our members the flexibility of lots and lots of different materials that they can choose from.

The important thing now is that they work their audiences that they’ve built up and get these materials in front of them, and that’s their audiences of leads and prospects as well as their existing clients. So they should be putting stuff about Windows 10 onto LinkedIn, sending out messages on LinkedIn, sending out emails, and especially shipping stuff in the mail to prospects whose addresses they have. And let’s be honest, it’s super easy to find any prospects address these days. Because if you remember the context that the average business owner or manager is not aware of this, it’s not on their radar, and therefore they’re not going to take action, this is a potentially massive opportunity for you.

This change is coming whether they like it or not. So really as the educator, as the expert, the local tech authority, you should jump on this and educate as many local business owners and managers as you can. And sure a ton of them are still going to leave their head in the sand and they’re not going to listen to you or any other MSP talking about this. But for some who suddenly notice that the technology that they run their entire business on is going to be obsolete from October, that will trigger some of them to want to do something about it. And they’re very likely to want to do that with the person that’s educated them, which should be you.

Ask this cybersecurity question to speed past phone gatekeepers

Tell me, are you in the 1% club. The 1% of MSPs who actually enjoy calling leads and prospects on the phone trying to find new business? Are you, no? Alright, well therefore I take it you’re in the 99% of MSPs that really struggle with this because for many it’s about the hell of getting past the gatekeeper. That person who seems to take enormous pleasure in stopping you getting through to the person you really want to speak to.

But yes, it is possible to fix this to get through, past the gatekeeper most of the time. And it’s all thanks to cybersecurity.

Let’s find out how one cybersecurity question can get you past the gatekeeper and start a much more productive conversation.

This is short and super simple. When you phone people and you’re trying to get past the gatekeeper to speak to the decision maker, do not say the classic old line, Who’s responsible for your IT? Don’t say that. They have heard that a hundred or a thousand times before. And when they’ve heard something many times before, it’s very easy for them to fob you off, say that person’s not in, lie and fib and ultimately end the call. So instead say this, Who’s responsible for your cybersecurity?

I can pretty much guarantee they won’t have heard that one before. And when they haven’t heard something, it’s going to make them pause and then start to think. And I reckon that you’ll stand a better chance of getting through to someone with that question. So here it is again. Write this one down