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There is a particular sentence MSP owners say with a shrug, as though it settles the matter: "I've tried salespeople — it never works out." It sounds like a conclusion drawn from evidence. More often it is the residue of a decision never actually made. In this conversation, Josh Peterson and Amnet founder Trevor Dierdorff pull that sentence apart, and what surfaces is not a story about bad hires but about a skill most owners never chose to build. Sales and sales management are different professions, and the founder who is genuinely good at the first has quietly promoted himself into the second without any of the study it demands. That gap — between owner-led selling and the discipline of building and managing a sales function — is where most MSPs quietly stall, and where the paradox that the owner who nails every call may be the worst-positioned to scale starts to bite.
What makes Trevor Dierdorff's account useful is his refusal to hide behind the shrug. Asked whether he ever invested in becoming a competent sales manager, he answers plainly: no. That honesty reframes the whole problem. The failed hires were not proof that salespeople don't work; they were proof that a rep dropped into an owner-led company without onboarding, activity management, or air cover was set up to fail. Underneath it sits a harder truth about leverage — an owner selling by force of personality is a ceiling, not a strategy, and the work of lifting that ceiling is unglamorous, deliberate, and entirely the owner's to do. The same pattern runs through everything else Dierdorff has built: culture, hiring, even his marketing, all succeed to the exact degree that he treated them as disciplines rather than accidents.
Owner-led sales lives on a spectrum, and where a company sits on it reveals more than any pipeline report. At one end is the owner who declares that no one can sell like him, so no one else will — a conviction that quietly caps the business at the founder's own calendar. At the other is the owner who sells only until he can find and develop someone who will eventually outsell him. The first is a personality masquerading as a strategy; the second is a plan with an exit. The distinction matters because the founder genuinely does hold an unfair advantage — a prospect buys differently from the CEO than from a rep — but an advantage that cannot be transferred is a liability dressed up as a strength.
The failed-salesperson story almost always ends with the rep blamed and the owner absolved. Dierdorff refuses that ending. His reps failed, he concludes, because he taught them his own owner-to-owner pitch — which they could never replicate — and because he never managed their activities the way he manages his technicians' time entry and tickets. A seller sent into the field on hope, with no onboarding path from rookie to competent and no accountability structure, is not a hiring failure; it is a management vacuum. The uncomfortable pivot is the owner admitting he never invested in becoming a sales manager, because that admission is the only door to fixing it.
Ask any MSP about its culture and you'll hear "good" or "great"; almost no one indicts their own. What separates claim from reality is intention, and intention is visible. Dierdorff greets his team each morning with "good morning, superheroes," fills a 127-year-old brick building with comic-book characters and mainframe hard-drive platters, and treats the whole environment as a deliberate signal rather than décor. The payoff is not vanity. A strong culture is the one battle an incoming salesperson doesn't have to fight — the sales-versus-service war that dooms so many first hires never ignites when the team already knows who it is. And when culture is weak, the bill comes due: Amnet once lost its largest and favorite client, and Dierdorff's verdict was that the team was dysfunctional and the fault was his. Culture, as the Italian proverb he cites has it, stinks from the head.
The instinct to protect a good culture can curdle into hiring clones, and Dierdorff's correction is sharper than "hire for fit." His culture is a recipe — beef, carrots, onions, all complementary, none identical — and the salesperson who breaks the mold isn't the problem. Chocolate chips aren't bad; they're just wrong for beef stew. The lesson is to hire for complementary attitude over pure aptitude, a shift he learned the hard way after years of weighting résumés over compatibility. The same patience shows up in how he markets: a prospect-focused podcast and an invitation-only executive forum that sell nothing directly and instead manufacture the know-like-trust that precedes any real MSP switch. Both are slow, both are deliberate, and both work for the same reason his culture does — because he treats relationship-building as a system, not a stroke of luck.
Not inherently. It's the right answer at certain stages and a genuine advantage — prospects often buy differently from the founder than from a rep. It becomes a problem only when it hardens into a permanent strategy that caps the business at the owner's personal capacity instead of serving as a bridge to a real sales function.
Usually because the owner teaches the rep his own owner-to-owner pitch (which can't be replicated) and never builds the onboarding path or activity-management structure a seller needs. The rep is set up to fail by a management vacuum, not by a lack of talent. Fixing it starts with the owner learning to be a sales manager.
They're distinct professions. A great salesperson identifies opportunities and closes; a great sales manager builds process, coaches reps from rookie to competent, and holds them accountable to activities. Promoting yourself (or a top rep) into management without that skill set is like making a great teacher a principal — a different job entirely.
A strong, intentional culture removes the sales-versus-service conflict that sinks many first hires. When the team already knows its identity and standards, a new seller integrates instead of igniting turf wars. Weak culture does the opposite and makes every sales hire a fight the owner is likely to lose.
Yes, when treated as a system rather than a hobby. Both work by building know-like-trust with identified prospects before any pitch — which matches how MSP buyers move, since they rarely switch providers without a strong relationship. The discipline is in feeding the top of the funnel and tracking conversion, not just recording episodes.
Trevor Dierdorff is the Founder and CEO of Amnet, a managed service provider serving Colorado's Front Range. He launched Amnet in 1998 as a side hustle while working as a PC technician, took it full-time in 2000, and has led the company for more than 26 years. Trevor is known for building an intentional, in-person company culture and for community-facing initiatives such as the Peak Executive Forum and the Pivot Point podcast, both designed to build genuine relationships with the businesses Amnet serves.
Connect with Trevor 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 owner-led sales has quietly become your ceiling, the path up runs through the discipline of building a sales function and a culture that sells for you — exactly the work the Vision Operating System is built to structure.
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