Many Managed Service Providers (MSPs) hit a ceiling when it comes to sales—not because their service quality is lacking, but because their sales process was never designed to scale. Referrals and local relationships can carry you for a while, but when you try to step out of founder-led sales and bring someone else in, that’s when things start to break.
In a recent Stride Live webinar, Stride’s team sat down with sales expert Robert Gillette, founder of the MSP Dojo, to talk about the sales pitfalls that plague MSPs and how to fix them. If you’ve ever struggled with inconsistent sales results, unclear quoting processes, or hiring that first sales rep, this one’s for you.
Here’s a breakdown of what we covered—and what every MSP should take away from the conversation.
Most MSPs Don’t Actually Have a Sales Process
Robert began by sharing a key insight: Most MSPs believe they have a sales process—but in reality, what they have is a series of habits. If you can’t write it down step-by-step or train someone else to follow it, it’s not a system. And systems are what enable sustainable growth.
“If you can’t explain your sales process on the back of a napkin in 30 seconds or less, it might not be a process. It might just be the way you do things.”
Why it matters:
A process you can’t document is a process you can’t repeat, train, or improve. That’s a problem if you’re looking to grow beyond founder-led sales.
Founder-Led Sales Can Only Take You So Far
Robert pointed out something many MSPs experience firsthand: it’s entirely possible to build a $1M–$2M business on referrals alone. But that approach won’t carry you into the next stage of growth.
The challenge comes when you hire someone to “handle sales” but can’t provide a framework for them to follow. Discovery calls stall, quotes never get sent, and even strong leads drop off—because the salesperson isn’t set up for success.
Ask yourself:
- Can your current sales process be followed by someone else?
- Would you want a new hire to do exactly what you do?
- Do they know what happens after the first appointment?
If not, it’s time to take a step back and assess what needs to be defined, documented, and improved.
Quoting Is a Critical Point of Failure
One of the most common breakdowns Robert sees is in the quoting stage. MSPs often reach the point where the prospect is interested—but they don’t have a consistent way to scope the work or create a proposal that speaks to what the client actually values.
This leads to:
- Overly technical or generic quotes
- Delays in sending proposals
- Missed opportunities because the value isn’t clear
How to strengthen this stage:
- Define standard offer sets or service bundles
- Use structured templates to scope needs quickly
- Tie every proposal to business outcomes, not just deliverables
A well-scoped, clearly written quote can be the difference between a signed contract and a stalled deal.
A Sales Process Needs to Be Repeatable, Trainable, and Testable
If you’re building a team—or even planning to in the future—your sales process needs to work without you. That means it should be:
- Repeatable: Others can follow the same steps and achieve results
- Trainable: You can teach it to a new hire within 30–60 days
- Testable: You can evaluate what’s working and what’s not, and adjust accordingly
Robert emphasized that a sales process isn’t something you build once and forget. It should evolve. When done well, you can improve it a little at a time—adding structure, refining language, and increasing effectiveness.
“Your process should be something you can iterate and make 1% better every time.”
Metrics Matter—Even Basic Ones
To improve your sales process, you need visibility. Start with just a few simple metrics:
- How many discovery calls lead to a proposal?
- How many proposals lead to a closed deal?
- What are the most common objections you hear?
Even basic tracking can uncover patterns and help you identify which part of your process needs attention. Over time, this data becomes your guide for optimization.
Start With a Strong Foundation—Before You Hire
If you’re thinking about hiring a salesperson, Robert offered one essential question: Are you a good example worth following?
In other words, if someone tried to sell the way you do, would they succeed? If the answer is no, you’re not ready to hire—you’re ready to build a process.
Rather than asking someone to step into chaos, take the time to document what works (and what doesn’t), map out key stages, and build the tools and templates they’ll need. That way, when you do hire, you’re setting them—and your business—up for success.
A Solid Sales Process Is a Growth Strategy
Sales shouldn’t feel like guesswork. A strong process empowers your team, improves your close rates, and ensures a better experience for your prospects. Whether you’re an owner doing it all yourself or starting to scale your team, now is the time to get intentional.
Because when your sales process is solid, predictable growth becomes possible—and sustainable.
Want to hear the full conversation with Robert Gillette?
Watch the full webinar replay on our LinkedIn
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This Stride Live Webinar is hosted by Stride Services. Stride is a comprehensive financial solutions provider, specializing in outsourced bookkeeping, accounting, tax, and advisory services for Managed Service Providers.
If you’re interested in being a featured guest on our Live Webinars or if there’s a subject matter expert you’d like us to interview, please and let us know!
