The MSP Sales Podcast

Episode 30 - Building the Modern MSP: AI, Cloud & UX (w/ Guest: Jim Spignardo)

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.
 
 
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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/hJKoFxgLearn 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 
 

Episode 29 - Selling Cybersecurity Without Fear In The AI Era (w/ Guest: Dor Eisner)

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.
 
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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/hJKoFxgLearn 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 
 

Episode 28 - Profitable Packaging: Fueling Predictable Growth (w/ Guest: Brian Hoppe)

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.
 
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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/hJKoFxgLearn 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 
 

Episode 27 - Lead Generation for MSPs: What Actually Works

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.
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"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/hJKoFxgLearn 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

Episode 26 - Lessons from Building, Selling, and Starting Over (w/ Guest: Colin Knox)

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.”
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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/hJKoFxgLearn 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 

Episode 25 - Marketing Works. Yours Doesn’t. Here’s Why. (w/ Guest: Johnathan Schofield)

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?
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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/hJKoFxgLearn 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 

Episode 24 - Standing Out in a Sea of MSP Sameness (w/ Guest: Paul Green)

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.
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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/hJKoFxgwww.FeelGoodMSP.com
#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing 
 

Episode 23 - How One MSP Owner’s Sales Shift Grew $70K in MRR (w/ Guest: Craig Bell)

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.
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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
 

Episode 22 - How MSPs Build Sales Confidence (w/ Guest: Brian Doyle)

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.
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Your next level of MSP sales starts at www.FeelGoodMSP.comLearn more about vCIO Toolbox at https://vciotoolbox.com
#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #vCIO
 

Episode 21 - Chaos to Clarity: Streamlining MSP Operations for Growth (w/ Guest: Ash Welsh)

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.comLearn more about Quoter at https://www.scalepad.com/quoter/
#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth