The MSP Sales Podcast

If you look under the hood of a stagnant MSP pipeline you will usually find the same thing. They are focused entirely on the wrong metrics. Cold email is saturated. LinkedIn messaging stopped converting a long time ago. The volume of activity was never the point. The conversation was. Nicole Bielanski is the Chief Revenue Officer at Frictionless IT. She started selling insurance at 19 and quickly topped a 400-person sales floor. She has spent nearly a decade building predictable go-to-market systems exclusively for MSPs. In this episode she reframes how we think about outbound and what pipeline actually means when the old channels no longer deliver. We cover: → Why optimizing for conversations separates winners from losers→ How smart list filtering eliminates wasted outreach → Why warm calling works when the prospect has a reason to take the call → How showing up in person is one of the highest-converting first touches…and a lot more. This episode is for the MSP owner grinding on outbound with nothing to show for it. You will walk away with a sharper picture of what a real go-to-market system looks like in 2026. -------------------------------------------------------------------------------------------- Learn more about Nicole via her LinkedIn. Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comBrian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format!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. .#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

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. The Big Takeaways?“The Death of the "Tech Guy" Value Proposition: Why the MSP of the future will either be a vCISO or won't exist at all, and how to stop selling tool stacks so you can start translating technology into business risk. The "Monkey Paw" Entry Offer: How to use universal baseline needs—like incident response planning and tabletop games—as the ultimate foot-in-the-door strategy to land larger accounts and displace incumbent competitors. SaaSifying Your Strategy and Pricing: Why pricing security on a per-user basis means you are going to lose your shirt, and how to structure modular flat-rate monthly retainers from $3,500 to $15,000. Climbing the 5-Layer AI Risk Pyramid: How to cut through the chaotic market FOMO and leverage AI governance to create a three-to-five-year runway of high-margin, enterprise-level advisory work. If you're trying to figure out where MSPs are headed next, this episode provides a roadmap. -------------------------------------------------------------------------------------------- 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.comBrian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format!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. .#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

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: → Why you should never ignore cyber insurance (and why you can't fill out the application for them) → The real reason claims got denied during the ransomware explosion → Why "sub-limits" are leaving your clients massively underinsured → The critical difference between cyber warranties and cyber insurance → How to use tabletop exercises to sell Incident Response (IR) planning → Why local insurance agents are the ultimate untapped referral source If you want to stop getting stuck in the crossfire of liability and actually use compliance to drive revenue this episode is for you. _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comLearn more about Andy Runyan on LinkedIn Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format!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. .#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

How would you start an MSP in 2026? Most would copy what’s already been done. Same services. Same pricing. Same positioning.That’s the problem. 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. → The 3 core offers I’d build: MSP, AI as a Service, and vCSO → How to sell outcomes (time, growth, productivity) instead of tools → How to reframe managed services as “insurance” (but why you shouldn’t lead with it) → Why most MSP marketing fails - and how to fix it without changing your stack 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. _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comBrian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format!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. .#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

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: How Virtuworks adopted SaaS to improve operations The importance of meeting changing customer expectations in 2026 Why automation is crucial for growing an MSP business How to adapt to the shift from service to software Listen in to hear how the managed services landscape is evolving, and why embracing software might be the key to staying ahead. _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comBrian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format!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. .#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

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: The personal habits that lead to professional success How your health can supercharge your business Why overcoming personal limitations is essential How to build a thriving business with the right mindset Don’t miss this inspiring conversation about the power of personal growth in business success. _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comBrian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format!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. .#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

Most MSPs don’t fail because of technology. They stall because the fundamentals of growth aren’t in place. In Episode 36 of The MSP Sales Podcast, Brian Gillette is joined by Tim Conkle to break down the three foundational elements every MSP needs if they want to scale beyond survival mode. This conversation dives into what separates MSPs that plateau from those that build real momentum - and why many owners focus on tactics before these core pieces are actually in place. In this episode, you’ll hear: → The 3 foundational ingredients every growing MSP needs → Why leadership maturity determines the ceiling of your business → Why sales and marketing discipline matters more than tools If your MSP feels stuck, overwhelmed, or inconsistent in growth, this episode explains what needs to change first. _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comBrian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", has just been released in audiobook format!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. .#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

In Episode 34 of The MSP Sales Podcast, Brian Gillette breaks down a hard truth. Most MSP owners learn the expensive way: not all “good advice” is good for you - at least not yet. Some advice is universal. Some is contextual. And some is only true in a specific sequence, after certain prerequisites have been put into place. In this episode, you’ll learn: → The 3 types of advice (and how to spot the difference) → Why “proven tactics” fail when your MSP is in the wrong stage → How MSPs waste money on PPC, lead gen, and automation too early→ Why hiring sales reps before your sales process is repeatable backfires If you’ve ever felt like you’re doing everything you’re told and still not seeing results, this episode will help you identify what’s missing: context, stage, and order. _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comRecent News:Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", has just been released in audiobook format!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. .#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

In Episode 32 of The MSP Sales Podcast, Brian Gillette is joined by John Snyder (CEO) and Neelesh Patel (President) of Net Friends for a candid, behind-the-scenes look at what it really takes to build a successful MSP - the wins, the mistakes, and the decisions that shaped where they are today. This isn’t a polished success story. It’s an honest conversation about growth through constraint, learning the hard way, and how a strong partnership became a competitive advantage instead of a liability. John and Neelesh share how they navigated leadership challenges, clarified roles, and built trust as the company scaled. Along the way, they dig into how Net Friends thinks about marketing, differentiation, and experimentation. This episode is packed with insights MSP owners can actually apply. In this episode, you’ll hear: ➡️ How a strong CEO–President partnership accelerates growth ➡️ The mistakes they made early - and what they’d do differently ➡️ Why clarity of roles matters more as MSPs scale ➡️ Creative marketing and AI ideas If you’re an MSP who wants to learn from people who’ve lived it - this episode offers a look at what sustainable success requires. _____________________________________________________ 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

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/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

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/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

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/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

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