The MSP Sales Podcast

Episode 20 - The Sales Fixation That’s Failing MSPs (w/ Guest: Wes Spencer)

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, and the courage to ditch old playbooks.
They unpack why so many IT providers struggle with growth, not because they lack tools or tactics, but because they’ve never been taught how to sell as themselves. Wes shares candid stories from his own journey as a founder and leader, and lays out a better path for MSPs who want more than temporary gains.
If you’ve ever felt uncomfortable in sales, struggled to connect with prospects, or just want to build a business that feels good and grows sustainably, this one’s for you.
 
-----------------Turn your MSP growth efforts into a sales machine!Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.
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#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #EmailMarketing #EmailStrategy #MSPMarketing 

Episode 19 - Cold Outreach That Actually Works (w/ Guest: James Milsom)

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 trust from the very first message.
Learn:
Why personalization isn’t optional anymore
What subject lines actually earn opens
How to avoid spam folders and show up with value
Whether you’re sending outreach yourself or guiding your team, this episode will help you stop guessing and start improving.
 
-----------------Turn your MSP growth efforts into a sales machine!Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.
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#MSP #MSPSales #ManagedServices  #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #ColdOutreach #EmailMarketing #ColdEmail #ColdCalling 

Episode 18 - Stop Killing Your Own Opportunities

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 clarity, these habits chip away at prospect trust and kill your sales momentum. And most MSP owners don’t even realize they’re doing it.
This episode isn’t about blame - it’s about awareness. Once you can see the pattern, you can change it, and then everything can shift.
-----------------Turn your MSP growth efforts into a sales machine!Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.
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#MSP #MSPSales #ManagedServices  #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining 

Episode 17 - Stop Winging It, Start Winning (w/ Guest: Mike Fielstra)

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, transitioning from outbound to inbound, and training MSPs to stop treating every lead like a sure thing. If you've ever worn too many hats in your business, Mike’s journey will feel all too familiar.
This one’s a must-listen for anyone who's tired of fluff and ready for real talk about lead management, client follow-through, and creating a process that respects your time.
-----------------Turn your MSP growth efforts into a sales machine!Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.
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#MSP #ManagedServiceProvider #ManagedServices #MSPSales #MSPMarketing #MSPCommunity #TechSales #ITServices #ManagedIT #CloudServices #ITConsulting 

Episode 16 - The Only Way Out Is Through

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 “perfect window” to make changes
Hoping a new wave of motivation will wash over you
He also shares his own moments of burnout, avoidance, loss, and what it really means to keep showing up when things get hard.
If you’re tired, stuck, or wondering if you’ve got what it takes... this one is for you.Because the only way out is through.
-----------------Turn your MSP growth efforts into a sales machine!Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.
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#MSP #MSPSales #ManagedServices #TechSales #MSPCommunity #ITServices #ManagedIT #SalesTraining #ManagedServiceProvider
 

Episode 15 - From Tech Geek to Trusted Seller (w/ Guest: Nigel Moore)

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-minded business owners face when they’re suddenly expected to be a sales leader. Nigel’s transformation from an introverted technician with sweaty palms to a trusted advisor who understands the true service behind selling is both inspiring and grounding.
If you’ve ever struggled with feeling “salesy,” or if your relationship with money gets in the way of making confident offers, this episode is for you. Whether you know Nigel or not, this conversation brings something new to the table.
-----------------Turn your MSP growth efforts into a sales machine!Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.
Learn more about The Tech Tribe at https://TheTechTribe.com/
#MSPSales #ManagedServices #MSPMarketing #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #MSPServices #ITConsulting #MSPBusiness#TheTechTribe #NigelMoore #SalesMindset #AuthenticSelling

Episode 14 - Rebuilding the Business You Actually Want to Run (w/ Guest: Michael Bakaic)

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 entire business around what actually felt good to create, sell, and deliver.
We talk about:
Why burnout is often a signal, not a failure
The difference between fixing your business vs. reimagining it
How simplifying his offer unlocked more freedom
Why storytelling closes sales
We also dig into the surprising evolution of Michael’s lead magnet - a cybersecurity audit tool that became his most effective conversation starter. You’ll hear how he repositioned a technical feature into a multi-stage trust-building funnel MSPs can actually use.
If you’re an MSP who’s hit a plateau, or is just tired of white-knuckling your way through growth, this episode is a powerful reminder that you can build something that works for your clients and feeds your soul too.Learn more about Iceberg Cyber at https://www.icebergcyber.com/
-----------------Turn your MSP growth efforts into a sales machine!Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.Learn more about Iceberg Cyber at https://www.icebergcyber.com
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#MSPSales #ManagedServices #MSPMarketing #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #MSPServices #ITConsulting #MSPBusiness#ITSupport #TechSupport #CyberSecurity

Episode 13 - The Truth About Leads and Growth (w/ Guest: Nate Freedman)

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 stall progress.
Learn how many MSPs are unknowingly sabotaging their own sales process, how to create justified outreach that actually builds trust, and why responding faster could be your biggest competitive edge. Whether you're just starting out or scaling fast, this is a must-listen for any IT provider ready to level up their sales game.
-----------------Turn your MSP growth efforts into a sales machine!Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.
.#MSPSales #ManagedServices #MSPMarketing #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #MSPServices #ITConsulting #LeadGeneration( Today's guest, Nate Freedman can be reached on LinkedIn or at  www.techpromarketing.com )
 

Episode 12 - Authentic MSP Marketing in a Skeptical Market (w/ Guest: Katie Vreeland)

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 relying on tired gimmicks, and creating marketing that actually connects. Whether you're an MSP owner doing your own outreach or you're leading a team, this episode will challenge you to think differently about visibility, awareness, and the customer journey.
Learn about building real trust without hype
Discover what actually resonates with today’s buyers
Reframe your marketing strategy to reflect your values and voice
Listen now and take your MSP marketing from forgettable to unforgettable.
-----------------Turn your MSP growth efforts into a sales machine!Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.
.#MSPSales #ManagedServices #MSPMarketing #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #MSPServices #ITConsulting( Today's guest, Katie Vreeland can be reached on LinkedIn or at  LuminaryCreative.co )
 

Episode 11 - SaaS vs. MSP Sales: What Works and What Doesn’t (w/ Guest: Tanner Cookson)

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 MSP owners need to know before making their next sales hire. From the importance of relationship-driven selling to the challenges of longer sales cycles, we explore what it really takes to succeed in MSP sales.
If you’re an MSP looking to build the right sales team, don’t miss this conversation! We’ll help you understand what skills to prioritize, how to onboard sales reps effectively, and why a strong sales process is just as important as hiring the right person.
🔹 What’s the biggest challenge you’ve faced in hiring MSP sales reps? Let us know in the comments!
-----------------Turn your MSP growth efforts into a sales machine!Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.
(Today's guest, Tanner Cookson can be reached on LinkedIn. ).#MSP #ManagedServices #ManagedServiceProvider #SalesStrategy #SalesTips #MSPSalesTraining #ITServices #MSPCommunity #ITConsulting #MSPMarketing #MSPSales #SalesHiring #SaaSSales #TechSales