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As most MSPs can attest to, prospecting can either thrive or fail depending on the approach. We’ve all heard plenty of horror stories, or maybe you’ve even experienced one yourself. But there are successes to be noted as well, and perhaps your MSP has an opening for a second or even a third business development rep! 

If you take only one thing from this article, remember there is no “silver bullet” to achieving success with outbound prospecting. 

In fact, outbound is more like a line of dominoes. Whether it works or not depends on how well aligned those dominoes are. 

The particular domino we are covering in this article is about the importance of finding problems the incumbent MSP can’t or isn’t willing to fix. 

Think about strategy before tactics

Most advice out there about outbound prospecting for MSPs focuses on tactics before problem-finding. Phrases commonly heard include: 

“The salesperson should dial 100X per day!” 

“Where will you get your prospect list?” 

And while these and many other processes matter, they are farther down the line of dominoes. 

MSPs should also think critically about their prospecting strategy. 

Imagine if your prospect wrote the following letter: 

Dear MSP Salesperson,  

Why are you leaving me another voicemail? 

I am responsible for a 34-person organization with millions in Opex and Capex per year. Why should I give you a chance? Is your solution really worth the hassle and pain of switching? 

What’s the quantifiable gain? What makes your MSP better and why should we pay a penny more? 

Your website says you are “proactive”, and my MSP’s website uses that same word a lot, too. And to be fair, our IT provider does a decent job resolving tickets – in fact, I rarely hear complaints from my colleagues. 

Look, I know you’re just doing your job as a salesperson – I get it,but do you see where I’m coming from? 

For example, do you really understand our biggest business threats (not talking about hackers)? I mean, can you help us build our product cheaper? Can you help us make better decisions with data? Can you make our factory more productive? Do you have an “easy button” for compliance? Do you know which LOB apps are causing the most headaches? Is revenue something you can influence at all? 

I’m willing to listen but I’m tired of talking about cybersecurity. Stop asking for money and tell me first how you will help me make more money.  

Identify challenges and pain points

Why do MSPs focus so much on tactics and activity volume and so little on strategy when it comes to outbound prospecting?  

I think you know the answer.  

It’s because many of your peers fear they have nothing unique to bring to the table.  

Some of you believe deep down that the only reason someone would switch to your MSP is because they are fed up with the incumbent and the timing is right. 

Let me share a story to help illustrate this: 

When I lived in Costa Rica back in 2010, a Presidential election was just getting underway. I’ll never forget the platform one candidate, Luis Fishman, was running on. His slogan was “El Menos Malo,” which roughly translates to “The Lesser Evil.” His belief was that enough voters would go for him because the other candidates were more corrupt. 

Now, was his strategy all that different from an MSP that believes outbound prospecting “is all about timing”? 

Look, Luis did not become the next president of Costa Rica, he came in last place, and while it’s true that timing is important for managed services, timing alone is not something I’d bet money on. 

Instead, in order for MSP outbound prospecting to work, we ought to identify the challenges that customers need to fix. Problems that go beyond solving support tickets and cybersecurity. Problems that help customers cut costs of goods sold, increase productivity, increase revenue, and minimize headaches that they lose sleep over. 

You may be losing sleep over cybersecurity threats, and for good reason, but your prospect doesn’t live in the channel, you do. 

Photo: Andrii Yalanskyi / Shutterstock

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Derek Marin

Posted by Derek Marin

Derek Marin is President of Simple Selling, the agency that generates predictable pipeline for MSPs. If you would rather tap dance in a minefield than add prospecting, marketing and sales team management to your to-do list, then feel free to book Derek directly from here: You can also reach him at or subscribe to the MRR Growth blog at for frequent sales tips and encouragement.

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