There is a version of the salesperson problem that almost every MSP owner has lived. Five years in, the person is likable, clients tolerate them, and they generate just enough revenue to make the conversation feel too risky to have. The problem isn't the salesperson. The problem is that the owner never built what a real MSP sales system looks like - no quota, no activity metrics, no defined expectations, no feedback loop. What gets called a sales problem is actually a structure problem, and structure is entirely within the owner's control. The listener email at the center of this episode describes a leadership failure, not a personnel one. Before any conversation with the salesperson can happen, the owner has to be honest about the fact that the game was never defined - and that's on leadership, not on the person playing a game with no rules.
Building a functional MSP sales system requires resolving two things in the right order. First, the owner must have a goal with genuine conviction behind it - a revenue target, a milestone, a vision of what the business is supposed to become. Without that, any quota assigned to a salesperson is arbitrary, and both parties quietly know it. Second, that owner's goal must translate into the salesperson's personal motivation. When both parties have a stake in the same outcome, the effort vs. results framework becomes something both parties want to work within - not something imposed from above. The two-quota model separates these cleanly: base pay purchases effort and activity; commission purchases results. Tracking them independently creates the visibility that turns gut-feel management into an actual operating system. And for owners wondering whether their hiring decisions compound the problem over time, the answer is almost always yes - but it's also a problem that can be corrected if you're willing to own it first.
When an MSP owner describes a salesperson as "inconsistent" and simultaneously admits there is no quota, no activity tracking, and no defined expectations, the diagnosis writes itself. There is no inconsistency problem - there is no system. What looks like underperformance is actually the natural output of a role that was never properly defined. The salesperson in this scenario isn't failing against a standard; he's operating in a vacuum the owner created. The email at the center of this episode captures a pattern that is almost universal in MSP businesses that have reached a certain size: the owner hired someone to solve a sales problem, never built the structure that would actually support a sales function, and is now several years in wondering why results feel unpredictable. The answer isn't a better salesperson. The answer is a defined game.
The owner's goal must precede the salesperson's target. This sequencing is where most MSP sales management fails before it starts. If an MSP owner cannot articulate - with genuine conviction - what the business is trying to achieve over the next one, three, or five years, any quota they assign to a salesperson is effectively arbitrary. And both parties usually know it. The correct order: the owner defines the company's revenue and growth destination, then works backwards to determine what the salesperson needs to produce to support it, then connects that production requirement to the salesperson's own personal financial goals. When those two vectors align - company goal and salesperson goal pointing in the same direction - the relationship changes. Accountability stops feeling like surveillance and starts feeling like partnership. The conversation becomes: here is what I need, here is what you want, and here is the math that connects them.
The structural failure inside most MSP compensation plans is treating base salary as a performance substitute rather than as a purchase of specific inputs. The correct frame is this: base pay purchases the activity - the prospecting calls, the first appointments, the pipeline creation - and commission pays for the results those activities produce. Separating these two functions creates two distinct, independently trackable quotas. An activity quota defines what the salesperson is expected to do every day and every week regardless of whether deals close. A results quota defines what the business expects to see in terms of revenue created. Managing to both simultaneously gives an owner something critical: the ability to distinguish between a salesperson who is doing the work and not yet closing (a coaching problem) and a salesperson who is not doing the work at all (a personnel problem). Without this separation, the owner is always guessing which situation they're in - and that ambiguity is exactly what allows mediocrity to persist for years.
When an MSP owner says "he's not the type of guy who'd respond well to accountability," what he's actually describing is his own reluctance to have a leadership conversation. The salesperson's hypothetical reaction is unknown. The owner's avoidance is certain. This is the pattern: the owner hasn't introduced structure, has no framework for the conversation, and so projects the discomfort of that void onto the salesperson. The reality is that most salespeople - particularly good ones - not only accept accountability, they actively want it. A scorecard gives them something to win on. It removes the ambiguity of wondering whether their efforts are being seen or valued. The owner who introduces a transparent, daily activity dashboard isn't punishing the salesperson - they're giving them the clarity that should have been there from day one. For the owner who has allowed years to pass without that structure, the correct opening is simple: we never clearly defined what success looks like in your role, that's on me, and we're fixing it now.
Start by taking ownership. The correct opening is not "you need to start hitting these numbers" - it's "we never defined what success looks like in your role, and that's on me." From there, you work collaboratively to establish the quota and activity metrics, framing the structure as something that helps the salesperson get what they want, not as surveillance. The transition period - typically 60 to 90 days - allows both parties to calibrate without the first week feeling like a judgment. The goal is clarity, not pressure.
Base pay purchases effort - the activity inputs that are required whether or not deals close. Commission purchases results - the closed revenue those inputs generate. The practical implication: base pay should be set at a level that is honest about the effort you're buying, not inflated to attract a candidate or retain someone you're uncertain about. When base pay is set too high relative to expected results, the salesperson has less financial motivation to perform, and the owner has less leverage to address performance gaps. The cleaner the separation between base and commission, the cleaner the accountability conversation will be.
Manage activity weekly from day one, and let that data tell you what you need to know within five to six weeks. If a salesperson is consistently hitting their activity targets, the results will come - and if they don't, you have enough information to diagnose why. If a salesperson is missing activity targets in the first month, you already have a problem. The insight is that you can identify a fit issue very early when you're managing inputs rather than waiting for outputs - and moving quickly when the inputs aren't there is a kindness to both parties, not a cruelty.
At minimum: number of prospecting calls or outreach attempts, number of first appointments held, pipeline value created, and active opportunities in progress. Three to four metrics kept visible daily is more effective than a complex dashboard reviewed monthly. The scorecard should be transparent to the salesperson - they should see the same numbers the owner sees, in real time. This removes the surveillance dynamic and creates shared accountability. Weekly check-ins against scorecard data are the management cadence; monthly reviews are for bigger-picture performance conversations.
This is exactly what activity tracking is designed to reveal. If the only deals in your pipeline originated from inbound inquiries, referrals from existing clients, or leads you handed off - and the salesperson's activity log shows no outbound prospecting - you don't have a salesperson. You have a capable follow-up resource, which has value, but is not the same thing. The solution is to define prospecting activity explicitly as a required component of the role and to track it separately from inbound activity. Once those two categories are separated, the picture becomes clear quickly.
Two questions in sequence: "Were you measured against specific metrics in your last role?" If the answer is no, you have your answer. If the answer is yes, follow with: "What would you score yourself against those metrics - and if I called your manager, what would they say?" The gap between those two answers tells you a great deal about self-awareness and accountability orientation. A salesperson who was not measured in a previous role has not been conditioned to perform within a structured system - and adding that structure later is much harder than hiring for it upfront.
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 co-hosts the BMK Vision Podcast alongside Josh Peterson, contributing an operational lens to leadership, growth, and business development conversations for the MSP market.
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 this episode made you rethink how your sales role is structured, the BMK Vision Operating System is built to put that structure in place - goals, milestones, initiatives, and the accountability layer that makes all of it work.
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