"Ray, great news!" (it wasn't)

A few weeks ago, I had a call with an MSP client. Let's call him Mark.

"Ray, great news! We just hired our first sales manager. Player-coach role. We also hired our first dedicated sales rep. Both are starting in two weeks on the same day. What pitfalls should I watch out for?"

I had to tell him something he didn't want to hear:

You're not looking for pitfalls. You've got three major problems already.

The Math That Doesn't Add Up

Here's what MSP owners miss: when you hire two new sales roles simultaneously, the complexity doesn't add up—it multiplies.

It's not 1+1=2. It's 1+1=3.

And that kills your success rate.

Each of these hires, individually, is a massive initiative.

Bringing on your first sales manager? It’s not a task to check off your to-do this week. That's your Rock for the quarter if you're running EOS.

Same if you’re hiring a dedicated sales rep.

A new sales manager needs playbooks, structure, daily check-ins, integration with the team. Even with detailed onboarding, you'll miss things because it's your first time. You're course-correcting constantly.

Your new rep needs their own onramp to get started: what the sales process is, the plans they’re selling, what makes you different, the tools and tech they’re supposed to be using, and that says nothing of the coaching and support to get started.

When you try both at once, you're figuring out two completely different things simultaneously. Neither gets the focus they need to succeed.

And here's the kicker: bringing on a sales manager in an MSP is notoriously difficult. Most MSPs burn through 3-4 sales managers before they get it right. Why? They don't know exactly what they're looking for. They hire someone from a big-company background who can't adapt to small-business sales. Or they hire a great salesperson who's a terrible manager.

It's really common for the first attempt to fail.

So why would you stack that risk on top of itself?

The Player-Coach Trap

Problem number two: the player-coach role itself.

If you need a sales manager, hire a sales manager. If you need a salesperson, hire a salesperson.

But don't fall for the player-coach fantasy.

Here's why it almost never works: being great at selling has very little to do with how great you’ll be at managing salespeople. The skill sets are entirely different. The mindset is different. You end up with someone doing one thing well and the other thing halfway.

Plus, if you're asking someone to sell, manage, AND build out your processes and playbooks—that's not a sales manager. That's more of a go-to-market (GTM) specialist, a highly skilled, expensive hire with the job description of building a sales organization at the strategic and tactical level.

And a good GTM person? They probably don’t want to start with a direct report they didn’t hire executing a process they didn’t help create.

The Authority Breakdown

Problem three is the timing itself.

Starting them on the same day destroys your sales manager's credibility before they even begin.

Picture this: your new sales manager walks in. Doesn't know your business yet. Doesn't know the process yet. Doesn’t have any answers.

But they have a salesperson reporting to them who also started on the same day.

How are they supposed to lead their new direct report? How are they supposed to establish any authority? How do they coach effectively? How do they have any credibility when the rep asks questions and the manager is still figuring it out themselves?

It's a setup for frustration on both sides.

So, what should Mark have done instead?

What Actually Works

Here's what I told Mark, and what I'm telling you:

Focus on one hire. Get clear on what you actually need.

If you need someone to build processes AND sell: Hire a GTM Specialist-oriented person first. Let them build your playbook, dial in your systems, start generating revenue. Then, 90 days later, they can hire the rep they want and set them up for success.

If you need a salesperson: Hire a salesperson and be prepared to be the sales manager (or hire fractional management). Look for someone with experience in consultative sales, ideally with a smaller brand that didn’t do the heavy lifting for them. And someone who’s a closer, not a professional networker.

(Here’s a video I recorded to help you find real producers, not professional interviewers.)

If you need a traditional sales manager: Bring them on. Give them a proper onboarding to integrate them into your processes, systems and team. Let them focus on leading and managing the sales team. Note, if you don’t have salespeople, you don’t need a sales manager.

Most businesses don't have the bandwidth to pursue multiple big initiatives like this at once. Either of these hires could rock your business in a positive way. Both together usually means both fail.

Pick your highest-leverage move. Execute it. Stabilize. Then come back for hire number two.

There's always more salespeople out there. But there's not always more time, money, and energy to burn through failed experiments.

Your Move

If you're planning to make sales hires in the next 90 days, ask yourself:

• What do I actually need first—someone to sell, someone to manage, or someone to build the whole system?

• Am I trying to do too much at once because I'm impatient?

• Do I have the bandwidth to set up two brand-new roles for success simultaneously?

The answers to those questions will save you six months of frustration and $50K+ in wasted effort.

Trust me. I've seen this movie too many times.

Adios,

Ray

P.S. If you're trying to figure out your sales hiring strategy, we’re have a pilot program helping a handful of MSPs recruit, hire, train, and manage an outside sales rep. We’ll open this up to more people in Q1, so if there’s any interest, just reply and we can share more info.