Growing an MSP from $2 million to $20 million is not the result of one successful campaign, a larger sales team, or a sudden increase in leads. Sustainable growth of your MSP sales system comes from building a clear, repeatable system that connects positioning, prospecting, sales execution, financial planning, and leadership.
In this episode of Stride Live, Casey Seaborn sits down with Brian Strong, CEO of TenHats, to discuss the systems and mindset that helped grow an MSP from approximately $2 million to nearly $20 million in annual revenue without relying on acquisitions.
Drawing on two decades of experience in the MSP space, Brian explains how owners can create a reliable outside sales engine, improve the quality of their opportunities, and gradually remove themselves from day-to-day selling. The conversation also explores the financial discipline required to support growth, including how to model revenue goals, evaluate hiring decisions, and understand the operational impact of scaling.
For MSP owners who want to grow recurring revenue while building a stronger and more valuable business, this discussion offers a practical framework for moving forward with greater clarity.
1. Stop Asking for More Leads and Start Defining the Right Opportunities
One of the most common frustrations Brian hears from MSP owners is that they need more leads. While that may be true on the surface, the deeper issue is often that the business has not clearly defined the type of prospect it is best positioned to serve.
More leads will not solve a weak positioning strategy. In many cases, they simply create more conversations with companies that are not the right fit.
Before increasing marketing activity, MSP owners should take time to understand what makes their business meaningfully different. This includes identifying the industries they serve best, the problems they solve most effectively, and the types of clients that create the strongest long-term relationships.
An MSP that is positioned as a general “computer company” may struggle to stand out. An MSP that is clearly known for cybersecurity, compliance, operational efficiency, or a specific industry has a much stronger foundation for attracting the right opportunities.
When the target is clear, the sales process becomes more focused, implementation becomes more manageable, and the business can grow without adding unnecessary strain.
2. Use Your Numbers to Reverse Engineer Growth
Once an MSP understands who it wants to serve, the next step is determining what the growth plan needs to produce.
Brian encourages owners to start by identifying their average monthly recurring revenue per client. That number provides a practical starting point for setting sales goals and evaluating whether the current target market can support the desired level of growth.
For example, if an MSP wants to add $25,000 in new monthly recurring revenue over the next six months, the path will look very different depending on its average client value. The business may need ten clients at $2,500 per month, or it may decide that stronger differentiation will allow it to pursue two or three clients at a significantly higher monthly value.
Both approaches can work, but they create very different demands on sales, onboarding, staffing, and service delivery.
This is why revenue goals should never exist separately from the financial model. Owners need to understand not only how much revenue they want to add, but also what that growth will require in marketing spend, commissions, labor, infrastructure, and cash flow.
Pro Tip: Start with the P&L, then work backward. A sales target is more useful when you understand exactly how it will affect the rest of the business.
3. Build a Prospecting Strategy Around Centers of Influence
Cold outreach can play a role in an MSP’s sales strategy, but Brian recommends placing greater emphasis on Centers of Influence, or COIs.
A Center of Influence is someone who works with the same types of businesses your MSP wants to serve. This may include bankers, attorneys, insurance professionals, consultants, accountants, or other trusted advisors who already have relationships with your ideal clients.
These connections are valuable because they create warmer introductions and often provide timely insight into companies that may be preparing for a change. A business going through rapid growth, leadership turnover, compliance pressure, or a recent cybersecurity issue may already be more open to evaluating a new technology partner.
Rather than approaching every prospect as a stranger, COI relationships allow MSPs to enter the conversation with a degree of trust already established.
That does not mean the relationship should be treated as a simple referral transaction. The strongest COI networks are built over time through shared value, consistent communication, and a genuine understanding of how both parties can support the client.
4. Create a Sales Process That Keeps the Conversation Focused
Even when an MSP reaches the right prospect, the opportunity can quickly lose momentum if the salesperson gives up control of the conversation.
Brian explains that prospects often withhold information early in the process because trust has not yet been established. When salespeople respond by immediately presenting services, tools, and features, they may provide valuable information without gaining a clear understanding of the prospect’s real needs.
This can lead to what Brian describes as “free consulting,” where the prospect gathers information, requests a proposal, and then uses that proposal to compare vendors without ever fully engaging in the discovery process.
A stronger approach begins with thoughtful, open-ended questions. Asking, “What prompted you to reach out?” gives the prospect space to explain what changed and why the issue matters now.
From there, the salesperson can explore the broader impact of the problem. A technical issue may be creating lost productivity, delayed projects, unnecessary risk, or personal pressure for the decision-maker. Understanding that impact allows the MSP to connect its recommendation to a meaningful business outcome rather than simply presenting a list of services.
5. Build Trust Through Expertise and Better Questions
Trust is essential in any sales process, especially when a prospect is considering handing over responsibility for critical systems, cybersecurity, and business continuity.
Brian distinguishes between trust that develops through likability and trust that develops through respect. While personal connection matters, respect is often established more quickly when the salesperson demonstrates a clear understanding of the prospect’s business and asks questions that reveal expertise.
This is where specialization becomes especially valuable. An MSP that deeply understands the operating environment, risks, and priorities of a specific industry can lead a much more relevant conversation than one that tries to serve every market equally.
Better questions also help the MSP determine whether the opportunity is truly a fit. The goal is not to force every prospect through the pipeline. It is to identify whether there is a real problem, whether the problem has a meaningful impact, and whether the prospect is prepared to address it.
When sales conversations are approached with clarity and curiosity, the MSP becomes a trusted advisor rather than another vendor delivering a pitch.
6. Create a Sales Engine That Does Not Depend on the Owner
Many MSP owners are the strongest salespeople in their organizations because they understand the business, the clients, and the service model better than anyone else.
However, that strength can eventually become a bottleneck.
When every important opportunity depends on the owner, the business has limited capacity to scale. The owner remains focused on active sales conversations instead of evaluating new service lines, strengthening leadership, improving operations, or preparing the company for its next stage of growth.
Brian argues that MSPs need a structured outside sales engine that can operate consistently without the founder carrying every opportunity. That requires a documented process, defined expectations, coaching, accountability, and a clear standard for how the sales team approaches discovery and qualification.
He shared the example of inheriting a sales team that had generated only about $8,000 in recurring revenue after seven months. After introducing training, expectations, and a consistent monthly target, the team went on to sell approximately $112,000 in recurring revenue over the following nine months.
The improvement was not driven by one dramatic change. It came from establishing a process, raising the standard, and helping the team believe that consistent performance was possible.
Pro Tip: A scalable sales system should be teachable, measurable, and repeatable. If the process only works when the owner is involved, it is not yet a true system.
7. Connect Sales Growth to Financial Discipline
A functioning sales engine creates opportunity, but growth still needs to be managed carefully.
Throughout the conversation, Casey emphasizes the importance of understanding how additional revenue will affect the P&L. New sales may require additional labor, higher commissions, expanded marketing, new tools, or more management capacity. Without a clear financial model, an MSP can grow revenue while placing unnecessary pressure on cash flow and profitability.
This is also why owners need to understand customer acquisition cost and payback period. The business should be able to explain, with reasonable clarity, how much it costs to acquire a client, how long it takes to recover that investment, and how the relationship contributes to long-term value.
Hiring decisions should be viewed through the same lens. Rather than filling generic roles simply because the team feels busy, MSPs should identify the specific gaps that are preventing growth or reducing service quality.
In some cases, the better decision may be hiring a specialist who can develop a new service line, improve delivery, or create a stronger differentiator. Strategic hiring is not about adding the most people. It is about adding the right capability at the right stage.
8. Accept That Operations Will Evolve as the Business Grows
One of Brian’s most practical messages is that operations will not remain perfectly stable during a period of significant growth.
Processes that work at $2 million may need to be rebuilt at $5 million, and the systems that support a $5 million business may need to change again as the company approaches $10 million.
That does not mean owners should ignore operational discipline. It means they should recognize that growth creates new demands and that some processes will need to evolve along the way.
Brian’s advice is to remain focused on building the sales engine while continuously improving operations as the business grows. Waiting until every process is perfect before pursuing new revenue can create stagnation, because the operating model will need to change again once growth resumes.
The more productive approach is to plan for that evolution. Teams should know that systems will be tested, responsibilities will shift, and lessons will need to be incorporated into the next version of the process.
With clear leadership and strong financial visibility, the business can continue moving forward without treating every operational challenge as a reason to slow down.
9. Why the $10 Million Milestone Matters
Brian views the $10 million mark as an important inflection point for many MSPs because it often represents the stage where the business has enough scale to build greater resilience.
At this level, the company may be able to support stronger secondary leadership, more specialized expertise, better departmental redundancy, and clearer operational accountability. Employees can take time away without every issue escalating to the owner, and the business becomes less dependent on a small number of individuals.
This level of maturity also affects enterprise value. A company that can continue operating without the founder’s daily involvement is generally more attractive to strategic buyers and private equity firms because the business is built around systems rather than one person.
Reaching this stage can also create opportunities for the MSP to become a buyer. With stronger leadership, reliable cash flow, and proven processes, the company may be better positioned to acquire another MSP, purchase a client base, or add a complementary service line.
The milestone is not important because of the revenue number alone. It matters because of what the business may be able to build with that level of scale.
Final Thoughts
Scaling an MSP from $2 million to $20 million requires more than ambition. It requires a clear understanding of the market, a disciplined approach to prospecting, a controlled sales process, and a financial model that supports each stage of growth.
The most important shift is moving from owner-dependent selling to a repeatable sales engine that can produce consistent results. Once that system is in place, the owner has more time to focus on leadership, service strategy, operational improvement, and the long-term value of the business.
Growth will create challenges, and some processes will need to be rebuilt along the way. However, MSPs that understand their numbers, invest in the right capabilities, and maintain a clear destination are better positioned to make those changes with confidence.
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About TenHats
TenHats helps Managed Service Providers build scalable outside sales organizations through sales strategy, coaching, leadership development, and growth consulting. Led by CEO Brian Strong, the firm works with MSPs to create repeatable sales systems that support sustainable, long-term growth.
About Stride Services
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.
Learn more at: https://stride.services
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Show Notes
Host: Casey Seaborn, Stride Services
Guest: Brian Strong, CEO, TenHats
Originally aired: July 18, 2026
