The Owner / Closer Dilemma 

I have come across a few MSP Owners this year who all shared a common view. While this is not uncommon, this particular view in my opinion is one that I don’t necessarily agree with. Despite their difference in reasoning, their mutual goal was to remove themselves from their company’s sales process completely.

While hanging it up might be fine for MSPs that have achieved scale, doing so before you’ve even crossed the $1 million threshold could be an invitation to a lot of unnecessary pain. Hiring for this role externally is incredibly difficult and this early on in your journey you likely don’t have a clear successor to appoint. 

Look, I get it. Sales can be an emotional roller-coaster, and carrying that around with you for years can be exhausting. If you are considering removing yourself from this role, then this article is for you. Here’s why MSP Owners make the best “Closers” and becoming comfortable in this role could be exactly what your business needs to achieve long-term growth: 

Authority & Credibility

Closing deals in B2B takes authority. I don’t make these rules, but it just does. This is why nearly everyone in Commercial Banking and Real Estate is a “Vice President.” That [business] card trick might work in other industries, but it can only take you so far in IT. Small businesses and enterprises are highly sensitive to technical change and they often need the security blanket of a truly authoritative figure to ease their concerns.

What I have also found is that MSPs rarely grow horizontally without moving slightly up-market in the process. This means that the need for authority actually grows as you start to engage with much larger customers. When these VIP prospects need more sales touches, it makes sense to put your best foot forward and lead with as much authority and credibility as you can muster. I’ve talked to CEOs of 8-figure MSPs who still hop on a plane to meet with a large prospect. Considering you will almost never outgrow this need, you might as well embrace it. 

Vision & Strategy

The trajectory of your business is decided with each new client you bring on. No matter what your vision is for the future, or how many meetings you’ve had to talk about it, your business won’t change until your prospects do. It’s easy for MSPs to fall into this trap, as they encounter opportunities and just say “yes” to any new revenue that comes their way. Don’t get me wrong, this also leads to some game-changing pivots, but the difference is whether or not the vision is there to support it.

Having an MSP Owner close to every deal guarantees the complete alignment between where the company wants to go and what they are actually selling to get there. This is contrary to a commission Salesperson who may be more willing to jump at the opportunity to take a deal, whether it maps well strategically or not. It’s possible to create a compensation plan that rewards the ideal behavior, but I’ve never met a Salesperson who was willing to just forfeit an opportunity without at least putting up a fight. 

Decision-Making Power

Occasionally a deal will come around that is so enticing that will actually make you question your entire business and go-to-market strategy. I can recall several of these moments from my days as an MSP. It’s not until you look back and plot them out do you realize just how impactful they are in your growth overall. The beautiful thing about having an Owner involved in the sales process is that you can capitalize on these opportunities in real-time, without the need for further deliberation. This is obviously because Owners have the ultimate level of decision-making power, and therefore you are essentially activating god-mode on every sales call. 

While this is great for the long term trajectory of the business, it is also ideal for the short-term decisions that impact the length of the sales cycle and a prospect’s willingness to move forward. For example, the prospect may want changes to certain legal terms or are looking to match a competitor’s price, which would require additional approval to move forward. Even the shortest delays in decision-making can give prospects enough idle time to talk themselves out of it altogether, or fetch other quotes that compromise the deal in hand. 

Personal Investment

One of my favorite parts of being a Business Owner is that it truly has the purest compensation model imaginable. When the business does well, you do well. When it doesn’t, then it’s on you to keep fighting until it does. While sales compensation plans apply some of this same logic, there is one key difference. A Salesperson has a parachute and an eject button that they can press at any time, carrying them off to work for someone else (sometimes taking your pipeline with them). MSP Owners don’t have this feature by default, and therefore, they have to stick it out no matter what the deal flow looks like.

This is important for the continuity of your sales process, which can often take months or years to develop as you grow. You want to build that process around someone that is highly invested in the success of the company and has staying power. If this doesn’t describe the MSP Owner, then the company likely has much more serious issues on their hands. 

Business Integrity

Being personally invested in your sales process isn’t just good work ethic, it’s also a great way to manage the integrity of how you sell. We’ve all worked with the occasional Salesperson over the years who will pitch anything that moves. While this can really come in handy, it can also go wrong in the worst ways. This is especially true in the incredibly nuanced industry that we are in, where it is so easy to over-promise and under-deliver, whether you intend to or not. 

Having the person who’s “name is on the door” leading your sales team will help to make sure that every deal closed is the beginning of a successful long-term relationship and not a disaster waiting to happen. Prospects understand this too, which is why interacting directly with the Owner of the company throughout the sales process often helps to lower the perceived risk associated with moving forward.

Long-Term Relationships

When it comes to Managed Services, “land and expand” is often the name of the game. While even large MSPs sometimes still only bring on 1-2 new customers per month, much of their revenue growth comes from upsells and cross-sells for existing customers. This is why building long term relationships is so important for MSPs, as it can lead to significant revenue growth later on in the company’s journey. 

While nurturing these relationships is often a function of Account Management and not necessarily a deal-closer, loyalty has to align somewhere. Having the MSP Owner ink the deal that begins the relationship ensures that the customer loyalty is anchored to the business and not a Salesperson that could just as easily leave. 

Storytelling Ability 

One of the reasons I personally like dealing directly with an Owner of a company is not necessarily their ability to tell me what I need, but rather how they explain why I need it. Owners and CEOs can speak directly from their experience in a way that few other people can. They can explain similar encounters that they’ve had, how problems were solved, and what they learned in the process. This narrative can act as a proof-point, which for me personally is typically enough to get me to buy.

As for MSP Owners, this is an opportunity to activate years (sometimes decades) of experience toward a good cause. Your ability to communicate through storytelling will go a long way in helping prospects better understand the technical nature of your work and why they need the services that you offer. Even if you are rehashing difficult situations that you would otherwise love to forget, it all helps to explain how your decisions are informed, and why they can be trusted. 

Conclusion 

I hope that by laying out this argument, I’m able to help MSP Owners better embrace the Closer role, rather than looking to offload it at the first opportunity. I understand that you want to be working on the business and not in the business, but without sales, you may not be working at all. Build a team around you to help with the appointment setting, quoting, presentations,  follow-ups, etc. and focus on doing what got you here in the first place; closing deals. You probably won’t regret it.