K7 Insights

How to Hire Your First Salesperson for Your MSP

By Kyle Christensen · June 8, 2026

Part of Grow Your MSP

Most MSP owners want to hire a salesperson so they can finally stop selling. That’s the wrong reason, and it’s half of why the hire so often flops. Here’s the real answer to how to hire a salesperson for your MSP: sell it yourself first, until the sale works without you being the smartest person in the room. Then hire someone to fill the top of the funnel, and stay the closer a while longer. Make the move from strength, around $2.5M to $3M in revenue, before a growth ceiling forces your hand. This piece covers when you’re ready and who to hire first. For the wider picture, start with how to grow your MSP.

Why do most first sales hires fail?

They fail because owners hire the wrong seat, at the wrong time, to solve the wrong problem. The wrong problem is trying to buy your way out of selling.

Here’s how it happens. You built the whole company’s sales on your own back. You are the sale. Every deal runs through you, because you know the stack cold and you can read a room, and it works right up until it caps you. A shop built entirely around the founder’s personality tends to stall somewhere around $5M to $6M, no matter how strong the founder is, and plenty of shops never get past it. So you decide the fix is a salesperson, and you hire one expecting a younger copy of you.

Week three, the calls sound clumsy and the meeting count is thin, and you write it off as a bad hire. It usually wasn’t. You skipped the part where a raw person becomes a seller, and that part is the actual job the day you stop being the only one who can sell. The hire didn’t fail. The plan for the hire did.

Who should you hire first, a BDR or a closer?

A BDR, the business development rep, almost always. The first seat you hand off is the top of the funnel. The close stays with you.

Think of your revenue work as three jobs. Marketing figures out who your best clients are. Business development finds those prospects and closes them. Account management keeps them and grows them. Right now you run all three, plus you own the whole thing. That’s normal early on. The mistake is staying all of them by accident.

When you do peel off a piece, the first piece is the cold outreach: the research, the dialing, the booked first meetings. Not because it’s the most valuable work, but because it’s the work you dread most, and dread is exactly what makes it the first thing to slip when delivery gets loud. That seat is the BDR. Their job is done the moment a qualified meeting is on your calendar. If you want the full picture of what that seat actually does all day, it’s MSP prospecting, start to finish.

The seat you hand off last is the closer, the account executive. Nobody sells your business with the conviction you do, so hand the close to a stranger too early and you’ll feel it in your close rate before you feel it anywhere else. The shape of a first sales team at most MSPs is one BDR feeding meetings to the owner, who’s still closing. Once that BDR is ramped and feeding a single closer, a reasonable bar is three or four solid first meetings booked every week. How many dials that takes is a function of your own conversion rates. Run the same backward math you’d run for your own selling, now scaled up for a full-time prospector instead of an owner stealing an hour between tickets.

When I was the hired operator on the hook for a shop’s $20M number, the first person I put on the funnel wasn’t a closer either. I kept the close and handed off the dialing, because the dialing was the part that fell off my own calendar first when the week got busy. The seat you hand off first is the seat you’re worst at protecting.

When are you actually ready to make the hire?

When you’ve proven the sale works without a superstar, and your margin can pay a salary through the ramp. That’s usually earlier than your gut says. Watch for three signs:

• The sale runs on a repeatable process. You’ve won deals on a motion you could write down and hand to someone else, without needing to be the smartest tech in the room. If you can’t put into words what a good sales meeting sounds like at your shop, you’re not ready to hire someone to run one.
• You’re around $2.5M to $3M and starting to feel the squeeze. You’re too buried delivering to feed the top of the funnel, and the funnel is the first thing to starve.
• Your margin can carry a base salary through the stretch before meetings become predictable, and the longer stretch after that before those meetings convert into signed clients.

Do not wait for the ceiling to start. The worst version of this is the owner who waits until growth stalls, then hires from panic with an empty funnel and no cash cushion, which is the hardest possible spot to coach a green rep through a rough first quarter. Start while the stakes are survivable. A failed hire at $3M is a bruise. The same failed hire at the ceiling, the year you needed it to work, is the company.

Jason Lemkin of SaaStr has watched hundreds of first sales hires play out, the wins and the wrecks, and he puts the timing bluntly: “Never, ever hire a VP of Sales until you have 2 individual sales reps really closing. Hitting quota.” The rule holds one rung down at the first hire too. You earn the right to hire the selling by first doing the selling.

One honest word about money. MSPs chronically underspend on sales, and it’s why the ceiling arrives for so many of them. In your growth years, plan to put 10% to 12% of revenue into sales and marketing, well above what most shops spend. That first base salary is real cash going out the door before any of it comes back, which is the whole reason to make this hire while your margin can still absorb the dip, well before things get too tight.

Should you hire one salesperson or two?

If the math clears, hire two. A single rep gives you no way to read what’s actually going on.

The idea isn’t mine. Jason Lemkin again: when you hire your first sales rep, hire two, because “no matter how well that rep does, you won’t learn anything. You need at least 2 to learn.” He’s talking about closers. I’ve ported it to the first BDR seat, since that’s where most MSP owners actually start. Give two reps identical scripts and an identical ramp, and they end up diagnosing each other for you. When a lone rep books nothing by week ten, all you can do is guess: bad hire, bad list, or bad plan? Run two side by side and a gap between them fingers the person, while both stalling in the same spot fingers your offer.

There’s a real cost, so be honest about it. Two hires means two salaries, two ramps, double the payroll you float before either one produces steadily. Redo the affordability check at two before you fall in love with the plan. If it won’t clear, phase it: bring the second hire on roughly two to three months after the first, leaning on the same ramp and scripts you already built, so that second salary hits the books once the first rep’s ugliest weeks are done. And if neither version pencils, one hire is a legitimate choice. Plenty of good small shops run a single seat on purpose. Just make the bet with your eyes open, because the whole year’s progress now rides on one person working out.

What do you pay a first sales hire?

Base plus variable. Never put a first hire on pure commission, because a managed-services deal is a long courtship, and a rep with no floor sells scared, and scared sells badly.

For a BDR filling the funnel, that’s a modest base plus a per-meeting bonus, guaranteed through the ramp so a rep who hasn’t booked much yet still sees a predictable check while the phone skills come in. For a closer, the going shape is roughly a 60/40 base-to-variable split, with the variable earned on the recurring revenue the client actually keeps paying, and part of it held back across the client’s opening months so a fast churn never lets the full commission cash.

That’s the shape. The full build is its own decision, worth getting right on paper before anyone’s first day: the multiple, the winnable quota, and the hold-back that survives churn. I walk the whole thing in the guide on MSP sales commission structure. Never offload a seat before you’ve settled how it gets paid.

Where do owners get the first hire wrong?

In the same handful of spots, and none of them are about the person’s resume:

• Hiring a closer first. You bring on an expensive account executive to replace yourself at the close before you’ve proven the close works without you. Now you’re paying a big number to a stranger who can’t sell your shop the way you can, and your close rate tells the story.
• Hiring to escape selling. The hire fills the funnel while you keep closing. It doesn’t carry the whole thing so you can disappear. Vanish from the numbers and they sag the week you stop watching.
• Skipping the ramp, so you panic in week three. Nobody books quality meetings in week one. A new BDR with no MSP background takes months to hit a meeting target even once, and longer before it’s reliable. Fire the first rep who’s shaky that early and you’ll keep firing them, hire after hire, because week three is rough for every single one of them.
• Expecting a clone. They walk in with a script and nerves. You have ten years of muscle memory. The gap between those two is the coaching job, and no amount of leaving them to sink or swim on their own is going to close it.
• Blaming grit when you starved the seat. When a rep is struggling, check yourself first. Are they getting enough at-bats off a live list? Is there anything they’re allowed to sell without your sign-off? Is your price somewhere the market will actually meet? Deciding the rep just doesn’t have grit is the most comfortable story an owner can tell himself, and it’s a bad read as often as a fair one.

That third-week panic is the one I watch owners lose to most. One owner I guided had finally hired a BDR, and three weeks in he called me ready to let the kid go: clumsy calls, no meetings. I asked what he thought a beginner’s third week was supposed to sound like. We held the line and coached the next call instead of grabbing the phone back, and by month three the rep was booking real meetings. He nearly fired the fix to his own problem. That week-three stretch is exactly where a plan saves the hire, and the one I hand owners is in the free book, Selling Without You.

Fix the one you recognize. You don’t have to run a flawless hiring process to hire your first salesperson. You have to stop making the one mistake that’s been costing you the seat.

Put it to work

Here’s the one thing to keep: your first sales hire fills the funnel so you can keep closing, and you make that hire while a rough start still costs you a bruise instead of the business. Sell it yourself until the sale works without you, then hand off the part you dread first. When the seat is filled, the next decision is what you pay it, so line up the commission plan before the rep’s first day, and check the whole hire against the growth system it feeds.

Then go make the call you’ve been circling for a year. Be accountable so you don’t have to be held accountable.