The MSP Sales Podcast

Brian Gillette
  • 5.0 (15)
  • Technology
  • Monthly

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.

  1. 2h ago

    Episode 66 - From $700K to $14M: 16 Years Selling for One MSP (w/ Mike Herrington)

    When Mike Herrington joined i.t.NOW 16 years ago, the company had seven employees and $700K in revenue. His very first managed services deal literally walked in the front door. In the 16 years since, it has never happened again.   Relying on word-of-mouth that just "happens" is like doing a rain dance. Over his 16-year career helping scale i.t.NOW, VP of Sales and Marketing - Mike Herrington built an irrigation system for leads instead.   In Episode 66 of The MSP Sales Podcast, Brian Gillette sits down with Mike to break down how to design simple sales comp plans, commission, and how referral partners can create unstoppable consistency.   We cover:  → How i.t.NOW scaled from $700K to $14M over 16 years → Why comp plans should be simple enough for a rep to calculate on a napkin → How to build an "irrigation system" by working referral partners in your CRM  If you're an MSP owner hiring your first sales rep or an AE tired of waiting on referral luck, this episode give you a blueprint to pay reps right and build a predictable pipeline. 🎧 Episode 66 is live on all streaming platforms. -------------------------------------------------------------------------------------------- Learn more about Mike Herrington via his LinkedIn. Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com 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

  2. Oct 26

    Episode 65 - Why Nobody Is Buying Your Managed Services

    Why Nobody Is Buying Your Managed Services You know your tech is good. You know you can help the business. So why are prospects still comparing you on price, going quiet after discovery, or choosing the cheaper MSP? The problem might not be what you're selling. It might be how you're selling it. In this solo sales training episode, Brian Gillette breaks down where MSP sales conversations go wrong, and how to fix them.   Here's what we get into: → Why selling your tech stack makes you sound like every other MSP → How to connect business problems to the outcomes you deliver → The "So What?" test for making your value clear → Why referral wins can hide flaws in your sales process → How the post-sale handoff shapes the client relationship   Brian shares practical frameworks you can apply to your own sales conversations, from discovery through to the post-sale handoff.   🎧 Episode 65 is streaming now on Apple Podcasts, Spotify, and YouTube. -------------------------------------------------------------------------------------------- Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com 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

  3. Oct 19

    Episode 64 - Money and Time: How to scale through the different phases of MSP Growth

    If you look under the hood of an MSP that has been stuck for ten years, you usually find two things. No spare time and no spare money. Every growth move costs one or the other. So the owner spends the little they have on conferences, certifications, and half measures. Word of mouth becomes the plan. In this solo episode, Brian Gillette draws one chart with money on one axis and time on the other. He walks through the phases of MSP growth, from the first clients to the phase five chasm. Then he turns the chasm into arithmetic. Define the investments, price them, and work backward to the leads, proposals, and clients you need. → Price your next two to three investments, then divide by net margin to find the MRR you need to sell → Work backward from close rate to proposals to leads → Profile your best five clients, then go where more of them gather This one is for the owner who pays the bills, has no time to spare, and wants a plan. You will leave with a target number and a first move. 🎧 Episode 64 is live. -------------------------------------------------------------------------------------------- Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com 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

  4. Oct 12

    Episode 63 - How 750 Closed MSPs Taught Me to Stop Churn (w/ Nick Wolf)

    Nick Wolf has heard that from hundreds of them. As employee #15 at Datto, Nick went on to close more than 750 MSP partners. At one point, he went 12 months without losing a single one of 160 active partners. What was behind that kind of performance? It wasn't some magic sales trick. It was how he built relationships, paid attention to details, and made sure people knew why he was calling. In Episode 63 of The MSP Sales Podcast, Nick and I get into: → Why your prospects probably don't see your MSP as different → How to make outbound calls that have an actual reason behind them → Why the handoff after the sale can make or break the relationship Nick has worked his way to the top at multiple companies in the MSP channel. There's a lot to learn from how he does it. 🎧 Episode 63 is live. -------------------------------------------------------------------------------------------- Learn more about Nick Wolf via his LinkedIn. Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com 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

  5. Oct 5

    Episode 62 - From Zero to $20 Million in Six Years (w/ Juan Fernandez)

    Most MSPs say they don't want to compete on price. Then they spend the entire sales conversation talking about technology, comparing stacks, and trying to prove why they're worth more. Juan Fernandez took a very different approach. He built an MSP from zero to $20 million in six years by focusing less on what he was selling and more on whether he could actually solve the client's problem. In Episode 62 of The MSP Sales Podcast, Brian Gillette sits down with Juan, Chief Encouragement Officer at MSP As A Service, to break down how he thinks about discovery, pricing, positioning, and winning the right clients. They dig into: → How to find out if there's actually a fit before you start pitching → Why "fake yeses" happen in discovery → Why most objections and "no's" walk into the meeting with you → How Juan uses a "soft close" built around guaranteed outcomes The bigger lesson? You don't have to win the price fight if you stop putting yourself in one. If you're tired of price objections, stalled deals, and prospects treating your MSP like every other IT provider, this conversation will give you a very different way to think about how you sell. -------------------------------------------------------------------------------------------- Learn more about Juan Fernandez via his LinkedIn. Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com 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

  6. Sep 28

    Episode 61 - Utility vs Asset: Selling Who They Become in MSP Sales

    If you look under the hood of a stalled MSP sales call, you will often find a parts list. Backup cadence. Delta files. Portal logins. The client is nodding, but nothing is landing. That is the lowest level of connection. It leads straight to the price objection, and you have nothing left to say. In Episode 61, Brian Gillette closes out the Feel-Good Close Foundations series with pillar three: build connection. This solo lecture centers on the connection chart. The shift is simple. Stop explaining what the service does. Start speaking to who the client wants to become. → Buyers see MSPs at the convenience or need level, so price gets questioned → Empathy in discovery is the antidote to FUD → Put the prospect in the driver's seat and act as the guide  This one is for MSP owners and sales leads who keep losing the conversation at price. You will leave knowing where your buyer sits on the chart. -------------------------------------------------------------------------------------------- Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com 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

  7. Sep 21

    Episode 60 - Sausage Making: The MSP Sales Habit That Kills Trust

    If you look under the hood of a stalled MSP sales call, you'll find the same habit every time. Too much talking. Not enough asking. Most discovery calls still run product-forward. XDR, RMM, endpoint detection. That's sausage making. Nobody wants to buy sausage by hearing how it's made. They care about what happens after they hire you. Brian Gillette continues the Feel-Good Close lecture series with pillars one and two. Focus on the solution. Fight for authenticity. He reframes discovery from product-forward to need-forward, and shows why curiosity, not charm, builds trust. He also unpacks the gap between forced honesty and real authenticity, and why disqualifying bad fits early is a responsibility, not an inconvenience. → Need-forward discovery leads with curiosity and surfaces it → Authenticity means aligning intent with words, not just being blunt → Selective hearing hides the red flags already in front of you  This one's for MSP owners and sales leads ready to stop pitching and start building trust. You'll walk away with sharper questions, a check on your own selective hearing, and a way to lead every call with the buyer's problem. -------------------------------------------------------------------------------------------- Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com 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

  8. Sep 14

    Episode 59 - One of Three: Why Great MSP Closers Still Lose

    There is a reason prospects lie to you before the pitch starts. It is not because they are bad people. It is because selling trained them to defend themselves. Most sales advice is tactics. Overcome objections. Handle pushback. Close harder. None of that explains why buyers show up guarded in the first place. This episode opens the Feel-Good Close Foundations series. Brian steps out of the interview chair to break down the adversarial sales complex, the pattern that turns sales conversations into a standoff. He names FUD as the fuel behind it, and empathy as the fix. → Why buyers default to the fake, take, escape pattern → Why fear, uncertainty, and doubt keep replacing trust in MSP sales → The one shift that breaks the adversarial cycle for good  This one is for MSP owners and sales reps tired of feeling like the villain in their own pitch. Walk away with a name for the pattern working against you, and the first piece of what replaces it.   -------------------------------------------------------------------------------------------- Interested in attending ScaleCon 2026? Register here with code FeelGood50 for a $50 discount: https://cvent.me/e9BBxL Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com 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

See All (67)

5
out of 5
15 Ratings

About

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.

Information

  • Creator
    Brian Gillette
  • Years Active
    2024 - 2026
  • Episodes
    67
  • Rating
    Explicit
  • Copyright
    © Copyright 2024 All rights reserved. Feel-Good Close
  • Show Website
    The MSP Sales Podcast

You Might Also Like