The MSP Sales Podcast
The MSP Sales Podcast digs into the philosophy, strategy, sales training, and techniques that allow a managed service provider to meet their maximum sales potential. For managed service providers who want to scale, we’ll discuss the critical systems that must be in place for every MSP to succeed. We’ll be joined by industry specialists in the IT industry to offer their expert insights. Hosted by Brian Gillette, his own unique and proven empathy-driven sales philosophy has helped generate millions of dollars in revenue for IT providers who deliver managed services including network security, backup, monitoring, compliance, and more.
Episodes
In Episode 30 of The MSP Sales Podcast, Brian Gillette sits down with Jim Spignardo, Director of Cloud Strategy & AI Enablement at ProArch, for a practical conversation about what it actually takes to build a modern MSP today.
With over 25 years in IT across networking, cloud, cybersecurity, and consulting, Jim brings a grounded perspective on how MSPs must evolve beyond tools and tech stacks. Together, they explore how cloud m...
In Episode 29 of The MSP Sales Podcast, Brian Gillette sits down with Dor Eisner (CEO & Co-Founder of Guardz) for a grounded, myth-busting conversation about selling cybersecurity in an AI-shaped world.
Too many MSPs feel pressured to become “cyber experts” overnight while many clients think cybersecurity is either too technical or too expensive to take seriously. Dor explains why both sides are looking at the problem the wrong...
In Episode 28 of The MSP Sales Podcast, Brian Gillette sits down with Brian Hoppe (Strategic Advisor and Revenue Coach to MSPs) to unpack why pricing, packaging, and financial clarity shape the entire sales experience. Not through pressure, scripts, or gimmicks - but through alignment, transparency, and knowing your numbers.
Together, they break down how the right packaging eliminates discounting, creates confidence in the sales pr...
In Episode 27 of The MSP Sales Podcast, Brian Gillette kicks off the new Lead Generation Series- a focused, no-nonsense deep dive into what actually works for MSPs looking to build a reliable pipeline.
Don’t waste time on the gimmicks, shortcuts, and “one weird trick” advice floating around out there. This episode breaks down the fundamentals of consistent outbound lead generation - how to use calls, emails, and events in a repeata...
What do you do after you’ve reached the top? You’ve achieved the dream - built the business, and made the exit. The pressure’s gone, and the question becomes - what now? In Episode 26 of The MSP Sales Podcast, Brian Gillette sits down with Colin Knox (Founder of Gradient MSP, Passportal, & MSPCentric) for a conversation that gets down to the realities of entrepreneurship — what drives us, what drains us, and what’s waiting on ...
Too many MSPs are still waiting for someone else to grow their business for them. In Episode 25 of The MSP Sales Podcast, Brian Gillette sits down with Johnathan “Skofi” Schofield, founder of FindMyITPartner.com, to unpack why so many MSPs feel stuck when it comes to growth. They break down why 77% of MSPs still rely on referrals, and what MPSs can do to start building trust on purpose instead of waiting for it to happen. They dig...
In Episode 24 of The MSP Sales Podcast, Brian Gillette sits down with Paul Green — one of the most respected voices in the MSP community — to unpack why so much MSP marketing looks the same and how to finally break free.
When every website, offer, and stock photo blends together, it’s harder than ever for prospects to tell you apart. Paul shares practical, battle-tested ways to brand yourself more authentically and make your market...
What happens when an MSP owner stops chasing leads and starts shifting how they sell?
In Episode 23 of The MSP Sales Podcast, Craig Bell joins Brian Gillette to share the sales shift that added $70K in monthly recurring revenue. This isn’t theory - it’s a real-world story about overcoming stalled deals, reframing the sales process, and finally gaining traction.
Together, Brian and Craig unpack: ✅ Why more leads don’t always mean m...
Fear and uncertainty hold back more MSP sales opportunities than most owners realize. You land the meeting, deliver the proposal, or finally get that chance you’ve been waiting for — and then doubt creeps in. The truth is, confidence isn’t something you’re born with. It’s something you build.
In Episode 22 of The MSP Sales Podcast, Brian Gillette sits down with Brian Doyle to unpack how imposter syndrome shows up in MSP sales — and...
Most MSPs focus on features, integrations, and the latest tools — but miss the bigger picture. In Episode 21 of The MSP Sales Podcast, Ash Welsh (Quoter team at Scalepad) joins Brian Gillette to talk about operational maturity, change management, and why simplifying your processes might be the best growth move you can make. Ash urges MSP leaders and team members alike to adopt a “business consultant” mindset:
✅ Evaluate tools for ...
What if the real sales differentiator isn’t what you say, but how human you are when you say it?
In Episode 20 of The MSP Sales Podcast, Brian Gillette sits down with Wes Spencer, co-founder of Empath MSP and one of the most respected voices in the industry. This isn’t your typical sales talk. Instead, Wes and Brian explore what it really takes to connect in today’s MSP landscape: emotional intelligence, human-first leadership, a...
Most MSPs fail at cold outreach. Not because it doesn’t work, but because they treat it like mass marketing.
In Episode 19 of The MSP Sales Podcast, James Milsom of Hunter.io joins Brian Gillette for a deep dive into what actually works in cold email - and what MSPs keep getting wrong. Backed by data from over 11 million emails, James shares hard-earned insights on deliverability, subject lines, personalization, and how to build tr...
Leads ignored. Quotes delayed. Opportunities ghosted.
In Episode 18 of The MSP Sales Podcast, Brian Gillette unpacks the quiet, often unconscious ways MSPs sabotage their own growth. It’s not about bad leads or weak marketing- it’s about hesitation, avoidance, and inconsistent execution at the time that it matters the most.
Whether it's pushing off sales follow-up, failing to respond in time, or delivering quotes that are missing ...
How do you go from selling water jets to selling IT services - and actually enjoy it?
In Episode 16, Brian Gillette talks with Mike Fielstra: a former MSP “hat rack” turned sales trainer at Tech Pro Marketing. Mike brings a refreshingly grounded take on the MSP sales grind, pulling from years of direct experience cold calling, chasing down leads, and managing client engagement.
He shares stories about handling 300-dial days, transi...
Let’s be honest: If you’re not willing to sell, lead, and face discomfort - you’re not building a business. You’re treading water.
In this episode of The MSP Sales Podcast, Brian Gillette calls out the quiet (often subconscious) habits that keep MSPs stuck:
- Hiding behind busywork
- Outsourcing sales before understanding it
- Waiting for that “pe...
In Episode 15, Brian sits down with Nigel Moore, founder of The Tech Tribe and a beloved leader in the MSP community. But this isn’t just another Nigel Moore interview. Here's why; Instead of retelling the greatest hits, Nigel speaks to us about something deeper: how his upbringing shaped his money mindset and how that mindset almost sabotaged his ability to sell. This episode is an honest look at the journey that many tech-minde...
What do you do when your MSP is technically successful - but you’re bored, burned out, or questioning whether you want to keep going?
In this episode, Michael Bakaic sits down with Brian Gillette and shares the honest story of how he hit a wall and what happened next. After years of grinding through service work that no longer energized him, Michael made the bold decision to pivot. He didn’t just tweak his offer; he rebuilt his en...
Why are MSPs still struggling with leads — even with great tools, teams, and marketing? In this episode of The MSP Sales Podcast, Brian Gillette sits down with Nate Freedman, founder of Tech Pro Marketing, for a raw and refreshing conversation about what it really takes to grow.
Together, they pull back the curtain on the real forces behind MSP growth: human connection, speed-to-lead, and the invisible mindset traps that silently s...
In this episode of The MSP Sales Podcast, Brian Gillette sits down with marketing strategist Katie Vreeland to unpack what most MSPs are getting wrong when it comes to marketing - and how to do it better. Together, they explore how personal branding, authenticity, and ethical messaging can cut through the noise in an industry where skepticism runs high.
Katie shares powerful insights about building trust, standing out without relyi...
Why might SaaS sales reps struggle in MSP sales? On the surface, selling software and selling managed services may seem similar - but the reality is, they require very different approaches.
In this episode of The MSP Sales Podcast, we sit down with Tanner Cookson (@ Alternative Payments) to break down the fundamental differences between SaaS sales and MSP sales. We discuss why many SaaS-trained reps struggle in MSP roles, and what ...
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