The MSP Sales Podcast

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 maturity, AI enablement, and user experience now intersect - and how ignoring any of them creates friction for clients and internal teams. They discuss; ➡️ Why “modern MSP” is more about experience than tech ➡️ How AI is reshaping service delivery ➡️ The role of cloud strategy in long-term MSP relevance ➡️ Why UX matters just as much for internal teams as end users ➡️ Common mistakes MSPs make when adopting AI If you’re an MSP owner, technical leader, or consultant trying to modernize your services, this conversation will help you think more clearly about where to focus.     _____________________________________________________ Have you heard the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)" It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values. Get it now at Amazon.com https://a.co/d/hJKoFxg Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing  #SalesTraining   

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 way, and how MSPs can simplify, educate, and lead with confidence. Together, they explore: ➡️ Why MSPs overestimate how much clients want to know about cybersecurity ➡️ How AI is already reshaping threat landscapes ➡️ A practical path for MSPs who feel “outgunned” by the pace of innovation ➡️ Why selling cybersecurity is really about risk reduction ➡️ The common fears that stall customer decisions Whether you’re an MSP owner, vCISO, or someone trying to meaningfully add cybersecurity to your stack, this episode will help you communicate value more clearly, close deals more confidently, and protect clients more effectively.   _____________________________________________________ Have you heard the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)" It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values. Get it now at Amazon.com https://a.co/d/hJKoFxg Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing   

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 process, and makes growth predictable instead of stressful. In this episode, you’ll learn: ➡️ How unclear packaging causes stalled deals and endless discounting ➡️ What finance numbers you must understand before you scale ➡️ The link between accountability, pricing, and recurring revenue ➡️ How your pricing model shapes your sales culture (for better or worse) ➡️ What good forecasting and predictable revenue look like inside an MSP This isn’t a conversation about “raising prices.” It’s a conversation about building a sales-ready business, one where your team can confidently sell, your clients know exactly what they’re paying for, and your growth becomes predictable instead of stressful.   _____________________________________________________ Did you catch the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)" It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values. Get it now at Amazon.com https://a.co/d/hJKoFxg Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing   

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 repeatable, measurable way to drive sales conversations. Want to know what separates MSPs who get consistent leads from those who stay stuck in “feast or famine” mode? Learn; ➡️ The truth about why most outbound fails ➡️ How to balance short-term outreach with long-term brand building ➡️ What to measure (and what not to obsess over) If you’ve ever wondered why your lead gen feels unpredictable, this episode lays the foundation for this series. Because real growth doesn’t come from hacks. It comes from doing the right work, consistently. _____________________________________________________ "How To Sell a Sh*tload of Managed Services (without selling your soul)" <--- A new book now available at Amazon. Written by Brian Gillette, Founder of Feel-Good MSP and host of the MSP Sales Podcast - it’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values. Get it now https://a.co/d/hJKoFxg Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #MSPLeadGen #LeadGeneratio #LeadGen

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 the other side of “making it.” Colin opens up about his own journey and shares hard-earned lessons from building, selling, and starting over — including: ➡️ Why chasing money rarely leads to fulfillment ➡️ How to define success beyond the spreadsheet ➡️ Why impact and purpose are stronger motivators than profit If you’ve ever wondered what separates “busy” from “fulfilled,” or what happens after the big win, this episode is the one. Because sometimes, the real work begins after you’ve already “made it.” _____________________________________________________ Did you catch the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)" It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values. Get it now at Amazon.com https://a.co/d/hJKoFxg Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com You can reach our guest Colin Knox on LinkedIn. #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing 

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 into the truth behind MSP marketing: ➡️ Why “marketing doesn’t work for MSPs” is a myth ➡️ How consistency beats complexity every time ➡️ Why referrals aren’t a growth strategy (and what to do instead) ➡️ How to manufacture trust before a prospect even talks to you This one’s a practical look at what it really takes to turn activity into traction. Because marketing works. Sales works. The only question is: are you working it? _____________________________________________________ Did you catch the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)" It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values. Get it now at Amazon.com https://a.co/d/hJKoFxg Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing 

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 marketing unmistakably yours: ➡️ Put your name and face front and center to build real trust ➡️ Create authentic content (even on a small budget) ➡️ Avoid “AI slop” - human stories always beat generic copy ➡️ Build charisma and confidence, even if you’re introverted If your campaigns feel invisible or prospects ghost you after the first touch, this episode will show you how to stand out, connect more deeply and become the MSP people actually remember. _____________________________________________________ Did you catch the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)" It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values. Get it now at Amazon.com https://a.co/d/hJKoFxg www.FeelGoodMSP.com #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing   

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 more sales ✅ The mindset shifts MSP owners need to close with confidence ✅ How training, coaching, and process changes can accelerate growth ✅ The practical steps that turned sales from stressful to sustainable If you’ve ever felt stuck chasing the wrong leads, struggling to move deals forward, or doubting your ability to sell, this conversation is for you. Tune in and learn how to rebuild your MSP sales process from the ground up. _____________________________________________________ Rebuild your MSP sales process from the ground up with www.FeelGoodMSP.com #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth  

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 how to move past it. They reveal why mindset, preparation, and process are the antidotes to hesitation, and how MSPs can turn self-doubt into steady confidence. You’ll discover: ✅ How reframing sales as helping changes everything ✅ Why process, preparation, and practice eliminate fear ✅ Practical ways MSPs can build lasting confidence If sales still feels uncomfortable, this episode is your playbook for breaking free from imposter syndrome - and winning with confidence. _____________________________________________________ Your next level of MSP sales starts at www.FeelGoodMSP.com Learn more about vCIO Toolbox at https://vciotoolbox.com #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #vCIO  

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 accessibility and usability, not just technical specs ✅ Anticipate change management needs during staff turnover ✅ Streamline and simplify processes so they’re easy to understand and communicate Whether you’re the CEO or a frontline team member, the ability to think critically about how you work — and how you can do it better — will directly impact your efficiency, profitability, and client experience. This episode offers actionable ideas you can put into practice right away. _____________________________________________________ Learn to rebuild your MSP sales process from the ground up at www.FeelGoodMSP.com Learn more about Quoter at https://www.scalepad.com/quoter/ #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth

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. . . #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #EmailMarketing #EmailStrategy #MSPMarketing 

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. . . #MSP #MSPSales #ManagedServices  #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #ColdOutreach #EmailMarketing #ColdEmail #ColdCalling 

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. . . #MSP #MSPSales #ManagedServices  #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining 

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. . . #MSP #ManagedServiceProvider #ManagedServices #MSPSales #MSPMarketing #MSPCommunity #TechSales #ITServices #ManagedIT #CloudServices #ITConsulting 

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. . . #MSP #MSPSales #ManagedServices #TechSales #MSPCommunity #ITServices #ManagedIT #SalesTraining #ManagedServiceProvider  

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

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 . #MSPSales #ManagedServices #MSPMarketing #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #MSPServices #ITConsulting #MSPBusiness #ITSupport #TechSupport #CyberSecurity

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 )  

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 )  

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