#19 – From the Trenches - MSP Growth - Sales, Structure & ‘Who Not What’ (Jim Smith)

There’s a specific kind of pain that only MSP owners understand: the moment you realize your “big win” client has quietly become your entire business model. In this From the Trenches episode of the BMK Vision Podcast, Jim Smith (Founder of Proper Sky) joins Josh Peterson to unpack what happened when Jim lost roughly 90% of his recurring revenue—and how that shock forced a better way of leading, selling, hiring, and building a durable MSP.

This is not a story about grit for grit’s sake. It’s about what the crisis reveals: that scale is less about technical capability and more about structure, delegation, measurement, and a willingness to stop “teaching cheaper people to do what you do” and instead hire people who can out-execute you in their lane. Jim frames the growth ceiling many MSPs hit (often around 10–12 employees) as a leadership tension: control vs. empowerment—and what it takes to move decisions down the org chart without losing standards.

If you’re an MSP owner trying to reduce concentration risk, evolve from technician to CEO, or build a repeatable sales engine without burning out your service team, this episode will feel less like advice and more like a mirror.

What does losing one “anchor client” teach you about MSP risk?

The obvious lesson is “don’t let one customer become 50%–90% of revenue.” The deeper lesson is harder: concentration risk usually isn’t a spreadsheet problem—it’s a leadership avoidance problem. When one account is feeding payroll, it creates noise that feels like urgency, and urgency crowds out the slower work of diversification, messaging, and intentional sales.

Jim’s story shows how fragile an MSP becomes when growth is accidental. The recovery required him to treat cash as fuel, build contingency thinking into planning, and stop confusing “busy” with “stable.” Diversification isn’t just a goal; it’s a discipline—one that must survive the very season that makes it easiest to postpone.

• Concentration risk is often visible long before it becomes fatal
• “Hope for the best, prepare for the worst” is a real operating principle—not a slogan
• Durability comes from a pipeline that’s intentional, not incidental

Why do MSPs stall at 10–12 employees?

Many MSPs don’t stall because demand disappears. They stall because the owner becomes the bottleneck—still holding the answers, still making the decisions, still solving the hardest problems. Jim describes the inflection point as a shift from “control” to “empowerment,” where the owner must trade speed (their speed) for scalability (the team’s speed).

The practical implication is uncomfortable: if everything still “trickles up,” you don’t have a service team—you have a human escalation policy. Scaling requires clearer outcomes, fewer prescriptions, and leaders who can run their departments without needing the owner’s fingerprints on every ticket workflow and internal debate.

• Owners can’t scale what they refuse to let go of
• Empowerment requires guardrails, not micromanagement
• Your job is to define outcomes and standards—not dictate every method

How should MSP owners think about sales: personality or system?

Jim and Josh treat MSP sales like service delivery: it has stages, inputs, follow-up rules, and measurement. The common failure mode is hiring a salesperson and calling it a “sales strategy.” That’s not strategy; that’s delegation without infrastructure. Without defined stages, tracked activity, and coaching time, the result is predictable churn and a dry pipeline.

The more mature posture is to build a sales engine where effort and results are both visible: calls, emails, first appointments, discovery, proposals, closes. Sales is not magic—it’s a repeatable process that improves when leaders stop hoping for “the right person” and start building “the right system.”

• Sales is a process, not a wish
• Marketing creates oxygen; the sales system turns it into momentum
• Owners must be able to inspect the machine—not just celebrate outcomes

“Who, not what”: what’s the hiring mindset shift that unlocks growth?

The most repeatable insight from Jim’s journey is simple: scaling happens when you stop asking “What should I learn next?” and start asking “Who should own this next?” Early on, MSP owners hire who they can afford and attempt to train them into excellence. That works—until it doesn’t. Past a certain size, you have to hire people who bring answers, not homework.

This isn’t about ego. It’s about speed, clarity, and quality. If it takes 18 months for an owner to “teach marketing” while marketing changes every six months, the business pays for that delay in missed pipeline and diluted positioning. Hiring smarter people isn’t expensive; it’s often cheaper than staying stuck.

• Hiring cheaper and “raising them up” often creates long-term drag
• Leaders accelerate by buying expertise, not reinventing it
• The owner’s highest value is vision, standards, and decision-making—at the right altitude

Episode highlights

• 00:00:00 – Losing 90% of MRR and the leadership reset that followed.
• 00:04:50 – Control vs. empowerment: why owners get stuck as the bottleneck.
• 00:24:21 – The “one big customer” trap—and how slow-motion failure shows up.
• 00:28:12 – Why owner-led selling matters and marketing is underutilized in MSPs.
• 00:45:16 – Measuring sales effort vs. results and building a real sales system.
• 01:04:20 – “Who, not what”: the hiring mindset that finally unlocks growth.

About the guest: Jim Smith

Jim Smith is the founder of Proper Sky, a managed IT services firm focused on helping organizations improve operational efficiency and security. Jim brings nearly two decades of MSP ownership experience, with hard-won lessons in leadership, sales systems, and building teams that can operate beyond the founder.

Connect with Jim Smith on LinkedIn →

Frequently asked questions

What’s the biggest risk of relying on one large MSP client?
Client concentration creates hidden fragility: it distorts hiring, cash decisions, and priorities—until the account shrinks or disappears and the business has no time to adapt.

Why do MSPs struggle to scale past 10–12 employees?
Because the owner stays the decision-maker for everything. Scaling requires outcomes-based leadership, empowered managers, and systems that prevent constant escalation to the founder.

How should MSP owners structure sales expectations?
Treat sales like a process: define stages, track activity and conversion, and coach consistently. Results improve when effort and inputs are visible and repeatable.

What does “who, not what” mean for MSP growth?
It means hiring expertise instead of trying to learn and do everything yourself. Growth accelerates when leaders bring in people who can out-execute them in specialized roles.

Related resources from Bering McKinley

• Bering McKinley helps MSPs hire the right sales manager
• Top indicators that your MSP needs a sales consultant
• Strategies for sustainable growth for MSPs

Want to continue the conversation?

If you’re an MSP owner trying to reduce concentration risk, build a real sales engine, and lead at the right altitude, we’d love to talk. Explore the Vision operating system or apply to be a guest on the podcast.

👉 Apply to be on the BMK Vision Podcast
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