The MSP Sales Podcast

If you look under the hood of a stalled MSP sales call, you'll find the same habit every time. Too much talking. Not enough asking. Most discovery calls still run product-forward. XDR, RMM, endpoint detection. That's sausage making. Nobody wants to buy sausage by hearing how it's made. They care about what happens after they hire you.

Brian Gillette continues the Feel-Good Close lecture series with pillars one and two. Focus on the...

There is a reason prospects lie to you before the pitch starts. It is not because they are bad people. It is because selling trained them to defend themselves.

Most sales advice is tactics. Overcome objections. Handle pushback. Close harder. None of that explains why buyers show up guarded in the first place.

This episode opens the Feel-Good Close Foundations series. Brian steps out of the interview chair to break down the adversar...

You walk into a networking event and start selling. That is the fastest way to leave with nothing.

MSPs treat these rooms like a numbers game, pitching everyone and hoping something sticks. People feel the agenda and shut down before you finish your sentence.

In this solo episode, Brian breaks down how he actually breaks the ice, at events and on cold calls. The reframe: you are not there to close. You are there to earn a secon...

If you look under the hood of a stalled MSP, you rarely find a bad market. You find one lead source, one excuse, and zero accountability.

Most owners want one channel to save them. When SEO does not hit in three months, they blame the tactic. When leads come in and they cannot close, they blame the agency.

Taher Hamid is back on the podcast - our first repeat guest! He runs MSP Camp, the Apex agency, and the ScaleCon conference. H...

If you look under the hood of an MSP that never grows, you will usually find one owner trying to do it all. That was Sergey Poltev, and it almost cost him everything.

He was overworked, stuck in the tickets, and running his life on empty. The burnout cost him his marriage and his house. Then, a bad partnership deal collapsed and cost him half of his clients, leaving him with barely enough to survive. 

If you are an MSP owner, ...

If you look under the hood of a stalled MSP sales process, you'll usually find the same six pieces of advice. Advice that sounds right. Advice that's been recycled from forum posts and LinkedIn threads until nobody remembers where it came from.

Most MSPs never test it. They just repeat it, and it slowly caps their growth.

In this solo episode, Brian pulls apart six sales myths making the rounds in the MSP space right now.

This one'...

If you look under the hood of a stagnant MSP, you will find a dysregulated owner.

Not a broken sales process.

Not a bad tech stack.

MSP owners carry a level of pressure that shows up on their faces, in their bodies, and inside their teams.

When stress goes unmanaged, it does not stay at the office.

It drives micromanagement, fractures relationships at home, and builds a team that depends on you instead of functioning without you.

T...

If you look under the hood of a stalled MSP pipeline, the wiring problem usually isn't marketing. It's everything sitting underneath it.

Ads and outbound only work as well as the foundation holding them up. Bad lighting on a sales call, no real CRM, no owned data list. These quietly cap what any campaign can do.

In this solo episode, Brian Gillette walks through seven investments, each under $1,000, that build trust and confidenc...

Revenue can climb for a decade. Net worth can stay flat the whole time. That gap is where most MSP owners get stuck.

Standard financial advice is built for salaried employees. Save a percentage, invest a percentage, wait for retirement. That breaks down when your income comes from a business and swings by six figures a year.

Justin D Maxwell has worked one-on-one with close to 1,000 seven-figure earners on this problem. He joins Br...

There is a quiet mistake sabotaging your biggest mid-market deals. It is how you price the first project.

Most MSPs chase the big RFP. Five hundred users, full boat, the whole suite. It looks like the dream deal. It is actually a bloody knife fight, and you only see three of the ten ways to lose it.

Adam Burke is VP of Sales and Partnerships at Quest, one of the largest MSPs in the country. He skips the RFP fight. He wins mid...

No mid-market CEO is waking up in a cold sweat hoping they can cut you a check for a list of cybersecurity frameworks and automated compliance reports. Most clients aren't looking for a "vCISO." They're looking for someone who can reduce risk, guide better decisions, and help them navigate an increasingly complex cybersecurity landscape.

The problem? Many MSPs are still selling technical expertise instead of business outcomes.

In ...

There is a common problem that sabotages your client relationships. It is not your pricing. It is not your tech stack. It is you. Let me explain;

Most MSP owners blame turnover, blame difficult clients, blame the market.

Shawn Walsh did that too, until he lost three quarters of his tech staff in one week and watched them try to steal his customer list.

In this episode, Brian Gillette talks with Shawn Walsh, CEO of Encore Strategic ...

This episode is for the MSP sales rep who's exhausted every digital channel and doesn't know what to try next.

And for the MSP owner who handed someone a blank slate and said, "Figure it out."

MSPs are sending emails nobody opens and making calls that go straight to voicemail. Every inbox is flooded with the same templates, sequences, and cadences.

But Ashton Fortuna found a different path.

After transitioning from cable puller to ...

If you look under the hood of a stagnant MSP pipeline you will usually find the same thing. They are focused entirely on the wrong metrics. Cold email is saturated. LinkedIn messaging stopped converting a long time ago. The volume of activity was never the point. The conversation was.

Nicole Bielanski is the Chief Revenue Officer at Frictionless IT. She started selling insurance at 19 and quickly topped a 400-person sales floor. Sh...

Most MSP owners think they know their numbers. The problem is... most don't. If you look under the hood of a stagnant MSP, the problem usually isn't sales. It's visibility. You can't improve profitability if you don't know where it's actually coming from.  Many MSPs chase growth without understanding which customers, agreements, or services are making money. The result is more complexity, more work, and often very little impro...

This was probably one of our most impactful and actionable interviews to date. Jesse Miller is, for my money, the absolute voice on vCISO. If you are trying to figure out where this industry is heading next, Jesse lays out the exact roadmap to stop playing the commodity "tech guy" game and start acting like a true strategic advisor.  

• The Big Takeaways? “The Death of the "Tech Guy" ...

Are you building a sales process or just avoiding doing the hard work?

A lot of MSP owners are stuck trying to build the perfect AI-powered Rube Goldberg machine. They want a system that sells for them. They obsess over tools, CRMs, and complex automations.

In this solo episode of The MSP Sales Podcast Brian Gillette breaks down why the exact skills that make you a great engineer are actively killing your sales numbers. He strips a...

If you are like me you hate talking about insurance.

You do not like the checkboxes. You do not like the technicalities. You certainly do not like the liability.

For a long time it felt like cyber insurance providers were just looking to make the MSP the scapegoat.

But the market has matured.

In Episode 43 of The MSP Sales Podcast Brian sits down with Andy Runyan from UKON Insurance to break down the real relationship between MSPs,...

Most MSPs think cold email stopped working.

The reality?

Most outbound campaigns fail before anyone even reads the message.

In this episode, Brian Kelly breaks down why deliverability has become the real bottleneck in MSP marketing, and why most providers are still approaching outbound the wrong way.

Brian shares how he applied a technical, engineering mindset to sales and built systems focused on one core principle:

“The bes...