Stride Live Webinar Recap with Robert Gillette
Raising prices is one of the fastest ways to grow your revenue—but for many Managed Service Providers (MSPs), it’s also one of the hardest moves to make confidently. What if your clients push back? What if you lose deals? What if you’re not really worth more?
But here’s the thing: most MSPs are already undercharging—and the barrier to better pricing isn’t the market. It’s mindset, clarity, and strategy.
In a recent Stride Live webinar, we sat down again with Robert Gillette, founder of the MSP Dojo, to talk about how MSPs can start charging more for their services, without losing trust or business in the process.
This isn’t just about increasing numbers on a proposal. It’s about understanding what your services are worth, knowing how to communicate that value, and structuring your pricing so it actually supports profitability.
Here are a few takeaways from our conversation, plus a few tips to keep in mind if you’re considering a price increase in the year ahead.
1. Most MSPs Aren’t Pricing Based on Profitability
Robert started the conversation with a common theme: many MSPs don’t have a clear rationale behind their pricing. When asked how they landed on their per-seat number, the most frequent answer is, “We looked at what others in the market were charging and picked something in the middle.”
“So it’s fictional. Got it,” Robert said.
Without understanding what it actually costs to serve your clients—and what kind of margin your business needs to grow—your pricing becomes disconnected from the reality of your operations.
Key Takeaway:
Pricing should be based on data, not guesswork. The better you understand your costs, the more confidently you can set pricing that supports your business.
2. Confidence in Pricing Comes from Clarity
As Robert pointed out, one of the biggest barriers to raising prices is a lack of internal conviction.
“If you feel like your pricing is made up, it’s really hard to convince someone else to pay it.”
Before increasing your rates, take the time to revisit:
- What value you consistently deliver
- What it costs to provide that level of service
- Why your approach is worth the investment
When you and your team believe in the number, it’s easier to stand behind it—and to communicate it in a way that makes sense to clients.
3. The Best Differentiators Are Client-Centered
Your pricing should reflect your value—and that value has to be clear to the client. Too often, MSPs rely on listing features or toolsets to justify their pricing. But technical specs don’t always translate to client outcomes.
Robert emphasized that your strongest differentiators aren’t always about what you do. They’re about what that work allows your client to do.
Instead of explaining every line item, focus on answering these questions:
- How does your service reduce risk, save time, or increase reliability?
- What would your client’s business look like without it?
- How does your support make their life easier?
The more clearly you can connect your work to their goals, the more trust you’ll build—and the easier it is to have pricing conversations that lead to “yes.”
4. Know the Math Behind Your Model
One of the most practical parts of the conversation came down to math. If you’re charging $200 per seat, and it costs you $150 to deliver, you don’t have room to grow. But many MSPs don’t have this data at their fingertips.
Consider starting with:
- COGS per seat (tools, labor, support)
- Target margin range
- Current client mix and support load
For most MSPs, a sustainable cost per seat lands around $60–$80. Anything above that should help cover your margin, team, and reinvestment in growth.
5. Price Increases Need to Be Supported—Not Just Announced
Finally, if you’ve decided it’s time to raise rates, the way you communicate it matters.
You don’t need to defend every dollar—but you do need to clearly show how your services support the outcomes your clients care about. This includes:
- Framing the increase around improvements or added value
- Reinforcing the quality, consistency, and reliability you provide
- Being proactive and transparent in your communication
Clients want to feel confident that they’re getting the right solution—not just the lowest price. When your messaging matches your value, they’ll understand why the number has changed.
Raising Prices Is a Strategic Step Forward
You don’t need to overhaul your entire offering to charge more. But you do need structure, confidence, and clarity.
Start by reviewing your costs. Refine your messaging. Align your internal belief with your external pricing—and take small steps forward from there.
Because when you know what your service is worth, pricing becomes less about defense and more about growth.
Want to hear the full conversation with Robert Gillette?
Watch the full webinar replay here on LinkedIn
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 let us know!
