The MSP Sales Podcast

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.  

If you're trying to figure out where MSPs are headed next, this episode provides a roadmap.

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Learn more about Learn more about Jesse Miller, the Founder of Powergryd.

Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com

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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 away the noise and brings it back to the five foundational questions you must answer before any marketing can work.

If nobody is buying your product it is time to sell a different product.

We cover:

→ How to repackage managed services as the foundation for AI adoption

→ Why you must clarify your positioning before you spend a dime on lead gen

If you are tired of overcomplicating your growth and want a straightforward path to closing deals this episode is for you.

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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, cyber liability, and security sales.

Andy explains why hiding from the insurance conversation is actually increasing your E&O risk. He also explains why playing the "cowboy consultant" and giving unlicensed advice is even worse.

Instead of avoiding the topic smart MSPs are using insurance requirements to force the hand on security controls and they are turning local agents into massive referral engines.

We cover:

If you want to stop getting stuck in the crossfire of liability and actually use compliance to drive revenue this episode is for you.

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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 best way to avoid being treated like spam is to stop acting like spam.”

We cover:

→ Why most MSP emails never reach the inbox

If your outbound strategy feels inconsistent, overcomplicated, or ineffective, this episode will challenge a lot of assumptions.

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Learn more about Brian Kelly's services at Automated MSP - an MSP-native AI-powered outbound prospecting platform that helps managed service providers generate qualified leads, recruit talent, build strategic partnerships, and identify opportunities via cold email automation.

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How would you start an MSP in 2026?

Most would copy what’s already been done.

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.

This isn’t about doing more. It’s about saying the right thing, to the right audience, in the right order.

If I were starting over today - this would be the playbook.

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Most MSPs get compliance completely wrong.

They treat it like a product.

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

This isn’t about adding another service.

It’s about changing how you think about value, risk, and your role in the client relationship.

If you’re trying to move upstream, get a seat at the table, and stop being seen as “just IT” - this is the shift.

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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 is essential for growth, and how customer expectations are evolving. Omar also explains why the traditional MSP model is fading, making way for a new, software-centric approach to IT services.

In this episode, you’ll learn:

Listen in to hear how the managed services landscape is evolving, and why embracing software might be the key to staying ahead.

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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 transformed from focusing solely on hard work to understanding the importance of balance and focus. The discussion moves into the evolving managed services landscape and why MSPs must adapt to stay relevant.

In this episode, you’ll learn:

Tune in to gain valuable advice on balancing business growth, personal health, and staying ahead in the fast-paced MSP world.

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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 addiction to becoming a marathon runner - and how these personal victories directly translated into business triumphs at VXIT. Learn how small daily habits and a commitment to self-improvement are the key to sustainable business growth.

In this episode, you’ll learn:

Don’t miss this inspiring conversation about the power of personal growth in business success.

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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 Foundations - a new, self-serve membership designed specifically for six-figure MSPs who want to build a real sales engine without the time or financial commitment of 1:1 coaching.

This is built for MSPs who need to fit sales into a busy schedule - and want a clear, practical system to generate consistent growth.

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