There is an email an MSP owner sends a peer roughly once a quarter. The wording varies, but the position is identical: I am serious about growing sales — why would I intentionally hire someone who does not know what they are doing? It sounds, on first reading, like a statement of operating discipline. Underneath, it is almost always a request for permission. Permission to skip the harder work of building a sales process. Permission to believe a senior closer will arrive and solve the problem one Tuesday afternoon. The position is wrong, but not for the reason it is usually argued. The reality is that the senior MSP sales closer most owners are chasing is mostly a fantasy — and even when one exists, the affordability math rarely supports a sub-five-million-dollar shop hiring them. The role-design move underneath that reality is the one most owners avoid. To build the muscle behind it, two prior conversations are useful companion reading: stop hiring people and start designing roles, and owner-led sales and dispatch discipline as the backbone of sustainable MSP growth.
What follows is not a manifesto for hiring cheap. It is an honest accounting of what the sales-hire decision looks like below five million in revenue, and how to make that decision in a way the business survives. The pattern is consistent across every MSP we work with at this stage: the owner believes the next senior hire will compound results faster than the cost; the candidate believes the comp plan more than the company; the pedestal goes up the moment the offer is accepted; and the accountability muscle quietly atrophies underneath the optimism. Six months later, ninety thousand dollars in salary is gone, the deals are still being chased, and the post is back open. The honest move is the one almost no owner wants to make. You are the closer. You need an opener. Hire green for that role, build the process the seat requires, and stay in the fight long enough to develop the funnel of talent that will eventually outgrow the seat. The discipline is not in finding the unicorn — it is in deciding you do not need one yet.
The senior MSP closer most owners describe in the job spec is mostly a fantasy. If the candidate exists at all, they were built inside another MSP, they are generally happy where they are, and they certainly are not leaving a real seat to join a 1.6-to-2.3-million-dollar shop they read as a career risk. The interview never converts. And in the rare case where it does, the owner has typically not done the second piece of math — the affordability matrix. The question is not how much revenue can this person generate. The question is what percentage of revenue can this seat consume without breaking the business. The first framing is a fantasy; the second is a budget. The first leads to ninety-thousand-dollar misfires that drag on for six months. The second forces a more honest conversation about what kind of seat the business can actually afford to staff today. Owners who skip the affordability matrix do not save themselves time — they pay for it later, in the form of compounding interest on a wrong hire.
The harder truth lives one layer below the affordability problem. Below five million in revenue, an MSP owner does not yet have the reference points to evaluate senior sales talent. The interview is not a place where this gets solved — it is the place where it gets exposed. The candidate has seen ten of these interviews this year. The owner has seen two. The asymmetric experience makes the interview unwinnable for the owner, and the candidate is not the problem. The absence of reference points is the problem. Owners who acknowledge this fact early get to make a different decision: they interview fifteen recruiting firms before they interview a single candidate, on the explicit thesis that the firm's job is to know what good looks like on the owner's behalf. Owners who do not acknowledge it post the job, accept the warm résumé, and rationalize the cost. The pattern is so predictable it is almost mechanical — and it is the single most common waste of capital we see at the sub-five-million stage.
What actually happens after the senior hire is accepted is rarely discussed honestly. The candidate, having been welcomed with a pedestal already half-built, settles in. The owner, having decided that experience is in the seat, relaxes the accountability muscle. The candidate name-drops a former employer's pipeline as if it were portable; the owner accepts the story because the alternative is admitting the hire was misread. Onboarding gets compressed because the candidate is "eager to get out there and sell." A deal materializes — always large, always six-to-nine-months out, always with a buddy the company has never served before — and becomes the new excuse for every short-term shortfall. The fundamental dynamic is the pedestal. The higher the pedestal at the start, the lower the accountability across the seat. And the salary surfer, who has done this several times before, is reading the room exactly correctly. The wave breaks in month five or six. The next base salary is already lined up. The MSP owner is alone with the math.
The constructive move is the one most owners avoid, and it is unflattering on first reading. At the 1-to-5-salesperson scale, the owner is the de facto closer. The customer is not buying a salesperson promising everything — the customer is buying the eye contact and judgment of the person whose name is on the building. This is not a flaw in the small-business sales motion; it is the small-business sales motion. The honest move is to name it, design around it, and stop pretending the next senior hire will solve it. For a fuller treatment of the right sequence of hiring and selling decisions before this conversation can even be productive, see the order of selling every MSP must know. The implication is uncomfortable: the role most owners need to hire for next is not the closer. It is the opener. The funnel feeder. The cold-call, knock-on-doors, take-a-stranger-and-turn-them-into-a-friend role that produces the conversations the owner closes. Designed correctly, the opener role does not require senior MSP experience — it requires hunger, coachability, and a process the owner has actually built.
Green does not mean clueless. Green means the candidate has not had a chance to develop the chops yet — and most have not because the seat that develops them is rare. The sourcing list for great green sales talent is unromantic. Prior service military. Collegiate athletes who never made it to D1. Servers and bartenders working a tough room for tips. Anyone whose lived environment has required them to take a stranger, make them comfortable inside thirty seconds, and convert them into a transaction. These people are durable, money-motivated, and largely invisible to the MSP industry's standard recruiting channels. The owner who notices them while ordering a sandwich and hands a card across the counter is doing something the recruiter cannot do — sourcing on character before résumé. The hire still requires a process. There is no version of this that works without one. But the cost of the misfire — and there will be misfires — is a fraction of the senior-hire misfire, and the accountability muscle the owner builds along the way is the most durable asset that comes out of the experiment. The longer-form companion to this idea, framed as a hiring competence problem, is you suck at hiring, and it is worth the read.
The single most expensive habit at the sub-five-million stage is not the misfired hire. It is the gap that follows it. The owner hires, the hire breaks, the owner retreats, and three-to-nine months pass with no salesperson on the floor at all. The funnel atrophies. The pipeline shrinks to what the owner can personally generate on a Friday afternoon between client meetings. The next hire arrives nine months later, against a smaller pipeline, into a quieter business — and the cycle repeats. The discipline is simple to name and hard to live: never not be hiring. Always be interviewing. The cost of a wrong hire is real, and exit should be fast and humane — but the cost of going dark on the seat is structurally larger. Stay in the fight, even when the fight is unpleasant. The hostage situations the owner most fears — the one big deal that has been dragging on forever, the account manager who is on probation but cannot be replaced because there is no bench — are made of the same material: a funnel that ran dry months before the symptom showed up. Green hiring with a process, an always-on interview pipeline, and a fast exit when the seat is not working are not three different disciplines. They are one discipline applied across time.
Three reinforcing reasons. First, the senior candidate is almost never as senior as the résumé suggests — the candidate pool below the unicorn tier is thinner than owners realize. Second, the owner does not yet have the reference points to evaluate senior talent and is structurally outmatched in the interview. Third, the pedestal that goes up at the offer kills the accountability muscle the seat actually requires. The combination is reliable enough to be predictable. The misfire is rarely a candidate problem — it is a role-design and accountability problem the owner inherited from the moment the offer was accepted.
The affordability matrix is the percentage of revenue an MSP can reasonably allocate to a sales seat without breaking the business. It is the opposite of the typical framing, which asks how much revenue can this person generate. Healthy mid-market MSP sales spend tends to land in the 8 to 12 percent of revenue range — fully loaded, including commissions, tools, recruiting, and time-cost. Below five million in revenue, that budget rarely supports a senior closer at market comp. Owners who skip the matrix discover the math nine months later, after the salary has compounded against an empty pipeline.
An opener creates conversations. They take strangers and turn them into friends — through outreach, calls, emails, events, and the unglamorous activity that fills the top of the funnel. A closer converts qualified conversations into signed business. They sit across the table from a buyer who is already considering the purchase and earn the trust required to write the check. At sub-five-million scale, the owner is the de facto closer in nearly every transaction. The hire that matters most at this stage is the opener — and that hire is much more findable, and much more affordable, than the unicorn closer most owners think they are looking for.
Not on the standard MSP recruiting channels. The best green sales hires tend to come from environments that have already trained them to read strangers, perform under pressure, and convert in real time — prior service military, collegiate athletes, servers and bartenders working tough rooms for tips. The sourcing happens in daily life as often as it happens in a recruiter's database. Owners who pay attention to who is impressive in front of them — and hand a card across the counter when the moment warrants it — find better candidates than owners who outsource the entire search.
Because they hire green without a process. Green hiring requires the owner to build the system the seat sits inside — outreach targets, weekly metrics, coaching cadence, go/no-go criteria, fast and kind exits. Owners who skip the process step end up in the same place as owners who hired senior without one — except they blame the candidate's experience level rather than the absence of structure. The discipline is the process. The candidate is downstream of it.
Some version of the answer is yes, and that is not a bad thing. The owner-as-closer dynamic tends to soften somewhere in the eight-to-ten-million-dollar range, when the company itself begins to do some of the trust-building work the owner used to do alone. Until then, the owner being the face the customer wants to see is a feature of the model, not a flaw. The discipline is not to outsource the closing — it is to design the rest of the system around the fact that the owner is doing it.
Gary Boyle is a Partner for Strategy & Business Development at Bering McKinley. With a background spanning network engineering, entrepreneurship, and strategic consulting, Gary brings real-world operator experience to helping MSP owners build stronger, more profitable businesses. He is a recurring co-host on The BMK Vision Podcast's Roundtable format, where he pressure-tests the leadership, financial, and operational decisions that determine whether an MSP grows, holds, or stalls.
Connect with Gary on LinkedIn →
Josh Peterson is the CEO of Bering McKinley and host of The BMK Vision Podcast. Since 2004, Josh has worked with hundreds of MSP owners to build operationally sound, profitable businesses through consulting, peer teams, and direct coaching.
Connect with Josh Peterson on LinkedIn →
If you are about to write the next sales job post — or quietly suspect the last one was a mistake — that is the place where the Vision Operating System does its most useful work. Decide what your sales seat actually has to do. Design the role around the funnel you have, not the funnel you wish you had. Build the process the seat requires. The hire matters. The system underneath the hire matters more.