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Why Sales Turnover Is So Costly for MSPs

Building a sales team is one of the most difficult and expensive challenges facing growing MSPs. Owner-led sales might feel like the safest option, but it’s more of a luxury than most people think. While time consuming, it’s also clear. You know the product, you know how to sell it, and you can improvise in the moment. Transferring that knowledge, capability, and instinct to someone else, however, is an entirely different challenge. Unlike technical roles that often have clearer paths to success, sales positions come with more risk, messier onboarding, and little consensus around what “good” actually looks like. For many MSP owners, it turns into a frustrating cycle: hire someone promising, watch them struggle, and eventually start over with less confidence and more skepticism than before.

To help make sense of why this keeps happening, we sat down with Brian Gillette, Founder of Feel Good MSP, and Robert Gillette, Co-Founder of MSP Growth OS. Both have coached MSPs through this exact challenge and have seen firsthand what works, what fails, and where most hiring efforts start off on the wrong foot.

The Cost Of Getting It Wrong

There’s a reason sales hiring feels so expensive and it’s not just about salary. Replacing a sales rep typically costs around 1.5 times their annual compensation when you factor in recruiting, onboarding, training, and the inevitable drop in productivity during ramp-up. On average, it also takes about 189 days to fill a vacant sales role. That’s roughly six months of missed revenue, stalled pipeline development, and added pressure on the rest of your team to keep things moving.

Robert Gillette put it bluntly when describing what happens when MSPs get this wrong. “They’re burning 50 to a hundred thousand dollars to ruin a person’s life (in the short-term at least). You’re going to burn an incredible amount of time, money, reputation, energy, and confidence from your staff that you know how to do this, and you’re going to ruin the dreams and crush the hopes of a young professional, and then blame it on them.”

The financial cost is only half the story. There’s also emotional damage and reputational strain that builds inside the company. When a sales hire flames out, people start to question leadership. Morale takes a hit. Owners begin to doubt their own process and wonder if sales is even a viable function in their business. As Robert puts it, “If you hire a salesperson in any industry, there’s a 75 percent chance they will not make it. If that was what it was like for your techs, you could not run a business, you just couldn’t.” And yet, that level of failure has somehow become an accepted part of how MSPs approach sales hiring.

Hiring Under False Pretenses

It’s easy to assume that most sales hires fail because they weren’t good enough. But more often than not, the real issue starts much earlier, during the hiring process itself. Many MSP owners unintentionally set the wrong expectations from the very beginning. Without a clear definition of the role or what success looks like, they end up describing a position that doesn’t actually exist. By the time the new hire realizes what they’ve walked into, the damage is already done.

This is especially dangerous in MSP sales, where the ramp-up period is anything but short. Selling managed services is hard. The sales cycle is long and often grinds on for months before showing any real signs of progress. It doesn’t matter how attractive the commission plan is if the rep is starting from zero and has no inbound leads to work with. The reward feels too far away, and most reps run out of steam before they ever get a real win.

Robert Gillette sees this happen constantly. “One of the things that I’m just tired of seeing happen is well-meaning young professionals being hired under essentially false pretenses.” This isn’t usually a case of deception. More often, it stems from the owner’s own lack of experience hiring or managing salespeople. “I don’t want to call them lies, because I don’t think the owner knows any better. I think they don’t understand what they’re doing, but they’re essentially hiring people… and I’m just like, can we stop doing that, please?”

When the story a rep is sold doesn’t match the reality they’re dropped into, it sets up a cycle of confusion, disappointment, and finger-pointing. The owner is frustrated by the lack of results. The rep is frustrated by the lack of clarity and support. In the end, both sides walk away feeling burned by a situation that could have been avoided with a little more transparency and a more honest evaluation of what the role truly requires.

Avoiding Setup for Failure

Once the rep is hired, many MSPs assume the hard part is over. But this is where most of the damage actually happens. Even if the right person is brought in, a lack of structure can sabotage their success before they ever get momentum. No scripts. No prospecting sequences. No clear metrics for success. And no systems in place to support the day-to-day work. What starts as “we’ll figure it out together” quickly turns into frustration and blame.

Brian Gillette puts it plainly. “They hire somebody, and there’s no process in place, and then they might even try to mentor or coach them, which just looks like beating them over the head every week with KPIs that they don’t understand, because they don’t have scripts, they don’t have sequences, they don’t have prospecting tools.”

This is one of the biggest misunderstandings about sales leadership. Coaching doesn’t mean repeating the numbers each week. It means building the system they operate in, then helping them improve inside that system. As Brian explains, “You’ve got to put process in, then put a person in who actually wants to use the process, refine the process, mentor them. If you do that, you’re much less likely to have turnover.” The success of your first rep will depend less on their raw talent and more on your ability to equip them. No amount of charisma or “grind” makes up for the absence of a plan.

Why Owners Are the Wrong Example

Many MSP owners fall into the trap of leading their sales hires by example. On the surface, that sounds like a good thing. After all, if you have successfully sold the service yourself, why not show the new rep how you did it? The problem is that owner-led sales is fundamentally different. You are not just another rep. You are the founder, the decision-maker, and the most credible voice in the room. Teaching someone to sell the way you do sets a standard they are unlikely to meet.

As Robert Gillette explains, “As the MSP Owner, you are actually a terrible example to follow. You have authority. You have acumen. You have leadership experience. You can negotiate anything you want for your MSP. You can stand toe to toe with a CEO as a peer.”

That context changes everything. When a junior rep walks into the same meeting without that kind of authority or credibility, the playing field is completely different. They cannot rely on the same confidence or shortcuts, and they often struggle to build momentum. Yet many owners expect them to succeed under those same expectations. “And you’re going to take some kid right out of college making forty grand a year, and you’re going to ask them to perform at that same level in that same way. Everything you teach them is going to be based off of your success as a business owner, and they’re going to fail miserably.”

This is where so many sales hires begin to unravel. Again, this is not a lack of effort. It is a mismatch between the owner’s approach and the reality of what a new rep can reasonably replicate. The solution is not to scale yourself, but to build systems that work independently of you.

Hiring the Right Persona

Once an MSP accepts that they cannot simply clone themselves, the next challenge is figuring out who to hire instead. This is where many owners make another critical mistake. They look for experience or polish instead of hiring someone who fits the current state of their sales operation. If there is no structure in place yet, what you actually need is a builder rather than a closer.

As Brian Gillette explains, “You need to hire a persona or a skill set that matches your level of sales operational maturity. So if you have nothing in place, you need to hire somebody who likes creating process.”

This becomes especially important when owners gravitate toward resumes from large or well-known companies. While those candidates may seem impressive, they are often not prepared for the reality of building from scratch inside an MSP. Brian offers a cautionary reminder: “If you’re hiring somebody from some household name company… they have no idea how to be a first rep, because they’ve only ever sold a product that everybody’s already heard of.”

Without a process, pipeline, or brand recognition to work with, your first sales hire will spend more time laying the groundwork than closing deals. That is not a step backward. It is the work required. Hiring someone who embraces that stage of growth instead of resisting it can be the key to finally turning the corner on sales development.

The Length of The Rope

One of the biggest miscalculations MSPs make when hiring a sales rep is underestimating the time it takes to see results. Owners expect to measure impact in a few months, but in reality, it often takes a year or more for a new salesperson to fully ramp up and generate meaningful return. This creates a gap between expectations and reality, and for many reps, that gap becomes the end of the road.

Robert Gillette puts the timeline in perspective. “You need to give a salesperson a much longer rope than you think, usually three times longer. It’s going to take at least three times longer than you expect for them to be successful.”

The issue is not just about patience. It is also about timing. Many MSPs end up cutting the rope just as the rep is beginning to gain traction. “They let a sales rep go just as they’re finally beginning to deliver a return on the investment.” That decision is usually driven by fear of continued expense with no visible payoff. But as Robert warns, “The truth is, you need to prepare for it to take three times longer than you want and three times more expensive than you planned. If you’re expecting to retire in the next few years, that rope may not even be long enough.”

Methodology, Process, and Accountability

If there’s one lever MSPs consistently underutilize in sales development, it’s structure. Most owners think they have a sales process, but what they actually have is a loose collection of habits, opinions, and vendor-driven pitches. That’s not the same as a repeatable, teachable system. Without clear methodology, process, and accountability, even the best sales hire will struggle to succeed.

Robert Gillette explains,“You could put them into a sales methodology and a process, which are two different things.” It might sound basic, but most MSPs are missing these foundational pieces. “The challenge is, most MSPs don’t actually have a methodology. What they have is, ‘we sell projects,’ or, ‘we sell whatever the vendor told us to sell.’ That’s not a methodology.”

Process alone is also not enough. Reps need mentorship and accountability to stay connected and effective. Brian Gillette reinforces this point. “You never outgrow the need for mentorship and accountability… you have to have the process in place for them to be able to follow, then they have to have guidance and coaching and outside help to hold them accountable, keep them encouraged, make sure that they’re connected to the rest of the organization.”

Building a Culture That Keeps Reps

Even if you get everything else right (the hire, the process, the training)  there’s still one more challenge to face. What happens when the rep actually becomes successful? Keeping them in the seat long term can be just as difficult as getting them productive in the first place. Once they start generating significant revenue, they also become attractive to larger companies, competitors, or even the idea of launching their own business.

Robert Gillette points out how fragile retention becomes once a rep realizes their value. “You still have this other problem of how do you get them to stay when they realize they’re adding millions of dollars to your revenue and hundreds of thousands of dollars to your EBITDA. What’s going to happen is Oracle is going to realize they’re pretty good and steal them for more money than you can pay, or they’re going to hire some tech guys and start an MSP. So even if you can find them and they’re successful in your system, how do you keep them?”

This is where culture and leadership matter most. Compensation is part of it, but so is connection. If a rep doesn’t feel supported, challenged, and understood, they will begin to isolate themselves — and that isolation leads to disengagement. As Brian Gillette suggests, “If you don’t provide accountability and outside perspective, sales reps end up in an echo chamber. They start building confirmation bias, then resentment toward anyone who challenges it, and that’s how they lose empathy and perspective, which makes them ineffective.”

Design Realistic Comp Plans

Unfortunately, the Glengarry Glen Ross days are over. No one is getting out of bed for a pat on the back and a set of steak knives. Sales reps today (especially younger generations) expect fair compensation without having to gamble their rent money to earn it. Yet some MSPs are still rolling out comp plans with no base salary, vague quotas, and a whole lot of “you eat what you kill” mentality. That approach is out of touch in a world where work-life balance is part of the benefits package. If your plan only works in theory (or a 90’s drama), no rep will stick around long enough to prove it out.

Brian Gillette has seen this mistake more times than he can count. “A lot of people will just blanket put ‘uncapped commission’ and think that that is like a carrot. I have not seen a sales job in the last decade that had a capped commission. There is nothing special about that, because commission is a lag indicator. It means they already made you money.”

The key is not just what the rep could earn, but whether those earnings are actually attainable. “On-target earnings need to be tethered to data. It cannot just be make believe. Quota has to be based on something. If it is not realistic, it is not motivating, and nobody cares about missing an impossible goal.” The point is that a comp plan should act like a roadmap, not an advertisement. If it is not grounded in clear expectations and believable numbers, reps will stop trusting it. That is when they will start looking elsewhere.

Conclusion

Sales turnover in an MSP is often a reflection of the system behind the hire. When roles are poorly defined, expectations are unclear, and support is inconsistent, even the most talented reps will struggle. Lasting success comes from designing a sales function that is grounded in reality and built with intention, not from rolling the dice on another hopeful candidate.

Robert Gillette highlighted how often reps are brought in without a real chance to win. Brian Gillette emphasized the danger of letting fantasy math and vague processes dictate compensation and performance. Both pointed to a truth that MSPs cannot afford to ignore. If your sales team is burning out or turning over quickly, the problem likely started long before the rep walked through the door.

Selling managed services is a long and complex process. It requires structure, financial runway, and the patience to let that structure work. The MSPs that figure this out do not just hire better. They retain better. They coach better. And over time, they build sales organizations that can grow steadily without constantly starting over.