MSP Sales Training: Why Most of It Fails, and What We Built Instead

MSP Sales Training: Why Most of It Fails, and What We Built Instead

Here's my bias, up front: I sell MSP sales training software.

So keep that in mind for the next couple thousand words.

But I've also spent over a decade inside MSP sales teams, hundreds of them, and personally trained over 300 BDRs to pick up a phone and book a meeting a prospect shows up for. So when I tell you most MSP sales training doesn't survive contact with a real call, I'm not guessing. I watched it fail, over and over, before I built something that doesn't.

What Is MSP Sales Training?

MSP sales training teaches your reps to sell managed services as a repeatable process: cold outreach, discovery, objection handling, proposal, close. Not a personality trait some people are born with and some aren't.

Real MSP sales training is specific to how managed services get bought. Legal, healthcare, manufacturing: your prospects don't buy MSP services the way they buy a CRM or a payroll platform, and generic B2B sales training doesn't know the difference between a break-fix shop and an MSP-ready account. It doesn't know what a vCIO conversation sounds like. It doesn't know that "we already have a guy" isn't an objection. It's a starting point.

Good MSP sales training also isn't an event. It's not a weekend, and it's not a binder your new hire skims once during onboarding and never opens again.

Why Most MSP Sales Training Doesn't Stick

Most MSP owners try one of three things.

They send a rep to a conference or a multi-day bootcamp, and the rep comes home fired up for about three weeks.

They hire a coach or join a membership community, get a framework with a catchy name, and hope osmosis does the rest.

Or they skip training entirely: hand a new hire a phone and a list, and call it sink-or-swim.

All three share the same flaw. None of them travel with the rep back into a real call. A framework you heard once in a hotel conference room doesn't show up on a Tuesday afternoon when a prospect says "just send me a proposal" and hangs up. Training has to live inside the sale, not next to it.

That's the whole premise behind how we built the Fox & Crow Group MSP Sales Process.

Training Built Into the Sale, Not Bolted On After It

Most MSP sales training hands every rep the same curriculum on the same day, whether they need it or not. Ours doesn't.

It assigns lessons based on actual performance gaps, not a fixed calendar. Every rep gets a different learning path each week, built from what their calls show they're missing, not what a syllabus says they should already know by week three.

It listens to and scores real calls, benchmarked against roughly five million MSP sales calls, not a coach's gut feel or a rubric someone made up in a workshop. Gatekeeper conversations, discovery calls, proposal meetings: every one gets scored, and the gap gets named specifically enough that the rep knows exactly what to fix before the next call, not "be more confident."

It builds pipeline, not just skill. Most MSPs still pay a monthly subscription for a tool like Apollo or ZoomInfo just to build a prospect list (anywhere from a few hundred to several thousand dollars a month depending on seats and data volume), and then still need a human to work it. Ours replaces that tool inside the same platform your reps are training in, at no extra charge. The lead generation and the coaching aren't two separate purchases from two separate vendors; they're the same system.

It includes a real coach when you need one, without the built-in monthly retainer. A decent fractional sales leader runs $2,500 to $5,000 a month and shows up every other week if you're lucky. Ours reviews every call your team makes, not the two someone remembered to send over before your check-in.

Why I Get to Say Any of This

I founded Managed Sales Pros in 2014. Two years later we hit seven figures in revenue: 625% growth in a single year, which landed us at #25 on Profit Magazine's list of Canada's fastest-growing startups. I exited that business in 2022.

Separately, I volunteered my time and training to build a call centre inside a men's detention facility, a project the Winnipeg Free Press covered.

I also built Everywhere Managed, a US based, on-premise call center that ran go-to-market programs for nearly every major vendor in the IT channel. I sold that business to EBQ.com in 2020.

I'm a graduate of the Goldman Sachs 10,000 Small Businesses program and the U.S. Small Business Administration's Streetwise MBA program, and I've been nominated for an Athena Award and inducted into the Las Vegas Women's Hall of Fame.

My co-founder, Ian Richardson, built and ran Doberman Technologies for over 20 years. An MSP that's landed on essentially every major award list in the IT channel, made the Inc. 5000, and swept Lansing, Michigan's entrepreneur awards, before he exited in 2021. He'll also tell you he personally burned over $1 million on failed sales hires before he figured out what works.

Between the two of us, we've had four successful exits and completed two acquisitions. We built the MSP Sales Process so nobody else has to burn a million dollars, or ten years, learning the same lessons.

Neither of us learned this from a textbook or a certification. We learned it running the calls ourselves, first.

Does This Work if You're Still the Only One Selling?

Yes. With a catch.

If you're a smaller MSP and you're still the founder carrying sales yourself, the platform runs the whole thing: it builds your pipeline, it scores your calls against that five-million-call benchmark, it assigns you the next lesson before you even know you need it. No BDR required, no team required.

The catch is the same one that shows up everywhere else in your business: the software doesn't make the calls for you. It'll tell you, precisely, what to fix after every one you make. You still have to pick up the phone.

How Fast Does This Change Anything?

Most MSPs see measurable movement in rep behavior within 60 to 90 days: shorter call hesitation, sharper discovery, fewer "just send me a proposal" stalls. Building a sales function that runs without the founder in every deal is a longer project, usually 6 to 12 months, because that's not a training problem. That's a documentation and hiring problem layered on top of training.

Anyone who tells you their weekend workshop fixes both in three days is selling you the workshop, not the outcome.

Sales Training Is a Growth Lever, Not a Personality Trait

You've already invested in delivery, in tools, in the technical side of the business. Sales is the part MSP owners consistently leave to luck, referrals, and whichever rep seems to have "the gift."

Document the process in a real MSP sales training playbook. Train from it. Score it against real data instead of a gut feeling. Do that, and sales stops being the department that runs on hope.

See exactly what the MSP Sales Process includes, then run the numbers on what this costs for your team size. Book a Fit Call after that. Twenty minutes, and I'll tell you honestly whether this is a fit. No pitch deck, no fake urgency.

Want to go deeper? The rest of this series takes these ideas into the real work: the common sales mistakes that quietly cost MSPs revenue, how sales coaching support changes rep performance, and the MSP sales training playbook that turns the framework into a repeatable process. Explore the posts to see what is holding your team back, how to coach against real calls, and how to build the process into your day-to-day selling.