The MSP Sales Podcast

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...

How would you start an MSP in 2026?

Most would copy what’s already been done. Same services. Same pricing. Same positioning. That’s the problem.

In this solo episode, Brian Gillette breaks down exactly how he’d go from $0 to $1M ARR today - without reinventing the tech, but completely rethinking how it’s packaged and sold. → The 3 core offers I’d build: MSP, AI as a Service, and vCSO → How to sel...

Most MSPs get compliance completely wrong.

They treat it like a product. They overcomplicate it. Or they try to charge a premium for something they can’t clearly define.

In this episode, Tim Golden (Founder and CEO of Compliance Scorecard) breaks down what compliance actually is - and how MSPs should be using it.

→ Why compliance is a process, not a tool → How to position yourself as a facilitator, not just a fixer → The si...

In this episode, Brian Gillette talks with Omar Armenteros, CEO and founder of Virtuworks, about the future of managed services and how SaaS is changing the game. With over 30 years in the industry, Omar shares how his company shifted from traditional break-fix models to software-driven solutions that scale and automate to meet today’s demands.

They discuss how this change is reshaping the way MSPs operate, why automation i...

In this episode, Brian Gillette speaks with Karl Palachuk, a prolific author and two-time MSP business owner, about his journey in the managed services industry. With over 25 books under his belt, Karl delves into his philosophy on success, focusing on relaxation, focus, and sustainable growth.

Karl also reflects on his battle with health challenges and how they influenced his approach to business and life. He shares how he transfo...

What does personal growth have to do with business success? A lot! Join Brian Gillette and Paul Vedder, CEO of VXIT, as they dive into how overcoming personal challenges fueled his professional achievements. In this raw, honest conversation, Paul shares the pivotal moments when shifting his mindset and committing to physical fitness reshaped not only his life but his MSP business.

Paul opens up about his journey - from battling add...

This is a bonus episode - and a different one.

If you’re here for a standard interview or tactical breakdown, feel free to skip this one. We’ll be back with a regular episode next week.

But if you’re an MSP owner who’s been following the podcast and thinking, “This makes sense, but I’m not ready for a full coaching program yet” - this is for you.

In this episode, Brian introduces MSP Sales ...

Most MSPs don’t fail because of technology.

They stall because the fundamentals of growth aren’t in place.

In Episode 36 of The MSP Sales Podcast, Brian Gillette is joined by Tim Conkle to break down the three foundational elements every MSP needs if they want to scale beyond survival mode.

This conversation dives into what separates MSPs that plateau from those that build real momentum - and why many owners focus ...

Most MSP owners don’t struggle because they lack technical skill. They struggle because they’re stuck operating instead of leading.

In Episode 35 of The MSP Sales Podcast, Brian sits down with serial entrepreneur and MSP growth strategist Shawn Freeman to unpack what it really takes to transition from hands-on operator to visionary CEO.

This isn’t theory. It’s about building scalable systems, integrating AI...

In Episode 34 of The MSP Sales Podcast, Brian Gillette breaks down a hard truth. Most MSP owners learn the expensive way: not all “good advice” is good for you - at least not yet.

Some advice is universal. Some is contextual. And some is only true in a specific sequence, after certain prerequisites have been put into place.

In this episode, you’ll learn: → The 3 types of advice (and how to spot the difference) →...

Word-of-mouth is the lifeblood of the MSP, but it is notoriously difficult to scale. In this episode, Brian Gillette sits down with Scott Millar (IT Rockstars), author of Virtually Irresistible, to discuss why webinars are the ultimate bridge between technical expertise and scalable relationship building.

Many MSP owners avoid webinars due to "tech anxiety" or a fear of public speaking, but Scott reframes the process as a repeata...