Brian Gillette on how to out-human MSP sales

The BS detector is on

⁠⁠In a world full of polish, Brian Gillette says the only way to win is to out-human the competition

⁠⁠Stumbling into managed services is practically a rite of passage in the channel. Brian Gillette is no exception, except that most people don't arrive via a decade of auditions, rejection, and performing arts. A background in Hollywood, modeling, live music, and theatre is not the most obvious background for someone who would go on to become one of the channel's most recognized voices on sales, and sales training for MSPs. But it is precisely that background that gives Brian Gillette his edge.

⁠From the stage to the server room

⁠Brian had been performing since he was a kid: choir, jazz big band, rock bands, talent shows. Deciding to make a career out of it, he moved to LA in his early twenties with $4,000, an air mattress. During his time in Hollywood, he had dozens of auditions and callbacks come his way. Among other things, he took part in a talent showcase where he walked away with more trophies than his suitcase could hold. Then came the role that should have been his, a part on Power Rangers that he chemistry-tested for all day, read with every other candidate, and lost because the female cast members were too short and he was too tall. That was the moment it clicked. Being the best has no bearing on whether you get hired.

⁠The casting director didn't pass on him because he couldn't act. They passed on him because of his height. The rejection said nothing about his ability. Learning to see it that way, clearly and consistently, changed everything.

⁠While yes, the experiences auditioning taught him resilience, it also taught him something more precise: how to hold his sense of self completely separate from the outcome in front of him. 

⁠This is, he says, the single most transferable skill from the stage to the sales floor. An actor who falls apart at every rejection doesn't last. Neither does a salesperson. But the ones who learn to separate the role from the person, the deal from their identity, can stay present, stay curious, and keep showing up. That ability to remain open and unguarded in the face of a no is precisely what makes the Feel-Good Close possible.

⁠"Until you've learned how to make that distinction in your brain, you're going to take any sales rejection or objection as a personal front to your character or your value. It wears away at you. And then you either harden, and that's where you get these adversarial, manipulative salespeople, or you learn to disassociate. That disassociation is directly a result of my experience as an actor."

⁠"I've been able to be more present and vulnerable and empathetic as a human because it doesn't cost me anything emotionally when someone rejects me."

⁠Into the channel

⁠Most people find their way into managed services through technology. Brian Gillette found his way in through a phone call. Sales had always been in his blood, and when an opening for a VP of Sales at a small MSP came his way, he took it without hesitation, despite not knowing the first thing about managed services. His first days on the floor were spent asking what MRR stood for and what the company actually did.

⁠But what he lacked in industry knowledge he more than made up for with process. He built a cold outreach system from scratch, trained a sales intern who had never sold a day in his life, and had him making a hundred calls a day. The intern booked one to two onsite meetings a week. Brian closed more than fifty of them. Within three years, with no marketing budget, no trade shows, and no SEO, he had nearly tripled the company's annual recurring revenue.

⁠The numbers were good. What he was seeing around him was not.

⁠The sales conversation nobody was having

⁠The IT industry, he quickly realised, had defaulted to fear as its primary sales tool. Dark web scans. Breach statistics. Compliance failures. And in some cases, outright fabrication.

⁠"I remember talking to one sales guy who would just make things up. He would do a dark web scan, didn't find anything compelling, so he would just make up a fake dark web report. They don't even know what the dark web is. They just have to believe him."

⁠For Brian, this wasn't just ineffective. It was wrong. And the methodology he had quietly been building while everyone around him leaned on fear would eventually become the Feel-Good Close.

⁠"People either run away and quit sales, or they fight and become adversarial, jaded, hardened. They start thinking of their prospects as the competition."

⁠For Brian, this wasn't just ineffective. It was wrong. And while everyone around him leaned on fear, he was quietly doing it differently. Leading with curiosity instead of urgency. Building trust instead of manufacturing it. This approach is what would eventually become the Feel-Good Close.

⁠Building something of his own

⁠Even while at the MSP, Brian had started to notice something. The methodology he had built wasn't just working for him. It could be taught. He had taken a tier-two IT guy who couldn't do field work anymore, handed him a sales process, and watched him book meeting after meeting. Teaching someone to sell, and watching it work, turned out to be just as compelling as selling himself.

⁠But success at someone else's company has a ceiling. By the time the pandemic hit, Brian had spent three years building something significant and was starting to ask harder questions about where it was all going.

⁠"I've made many people millionaires in my life, but I'm nowhere near a millionaire. And the CEO actually told me: Brian, I think you're an entrepreneur. I think you're supposed to be running your own thing."

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⁠He left in August 2020. What followed was a period of genuine uncertainty: a consulting contract that ran longer than expected, a stint on unemployment, and a failed attempt at coaching female entrepreneurs that went nowhere fast. Then, in July 2021, he pivoted back to MSPs.

⁠"I started this thing called the Million Dollar MSP Challenge. I went on LinkedIn and cold-called MSPs. Six people registered. Five attended. Three bought. I thought: okay, maybe there's something here."

⁠He built the curriculum the same way he had figured everything else out, by doing it in real time. He would walk around his neighborhood talking into a transcription app, turn the transcript into a syllabus, deliver a live session, then do it again the next day. Two weeks of that became eight weeks of courses he used for three years.

⁠That scrappy, self-built origin is now Feel-Good MSP: a sales training membership, a podcast, and a book whose title, How to Sell a Shtload of Managed Services (without selling your soul), says more about the state of MSP sales than most industry reports do.

⁠The Feel-Good Close

⁠Months of selling, teaching, and refining eventually crystallised into something concrete. The approach to sales that Brian had been practicing since his earliest days in the channel became what we know today as the Feel-Good Close methodology.

⁠At its core, it rests on three principles: focus on the solution, fight for authenticity, and build connection. 

⁠Simple enough to state, harder to practice in an industry that had spent decades doing the opposite.

⁠"Questioning a prospect's beliefs that are holding them back is the highest form of respect in sales. And life and business are meaningless if you aren't building a network of relationships as you go."

⁠Central to the methodology is a reframing of what a sales conversation is actually for. Brian asks his clients to think of conversations as farms, not mines.

⁠"Don't connect with people to take something from them. Connect with people to build something of value with them. Instead of listening for what you want to hear, listen for the truth. This creates more authentic conversations, resulting in higher trust, faster conversations, and more sales."

⁠Curiosity, he argues, is not a personality trait. It is a byproduct of genuinely caring about the person across the table.

⁠"Traditional sales training tells you to provoke specific responses from prospects and then respond with rehearsed talking points. Curiosity is what happens when you stop doing that. When you care about the people around you, you will be more inquisitive."

⁠And when it comes to building a sales team, he is looking for one thing above everything else.

⁠"What scares me about hiring for instinct is that people with natural talent often lack resilience. If things have always come easy to them, they don't know how to fail. Being consistent in the face of failure is the most valuable skill in a salesperson."

⁠Selling in an AI world

⁠The world Brian built Feel-Good MSP to address is changing faster than anyone anticipated. AI is reshaping how MSPs market, prospect, and communicate. 

⁠"It's harder to sell traditional managed services today than it was five years ago. Users are more advanced and technology is simpler to interact with. You have to find a reason for the business to care about your service and keep caring about it for a long time. "

⁠The answer, he says, is not to produce more content or build a slicker outreach machine. It is to be more human, more specific, and more willing to show up in ways that cost something.

⁠"UGC creators are posting blurry front-camera videos of themselves brushing their teeth and getting millions of views. Meanwhile the high-production ads in a white studio are getting scrolled over. Focus on creating a tribe around your core mission, create raving fans who've had meaningful results, and ask them to tell people. Let everyone else make videos of Keanu Reeves installing servers in space while you change your customers' lives."

⁠Brian is not against technology. But he draws a clear line between using AI to free up time and using it to replace the thing that actually wins business.

⁠"I urge everyone to stay human. Don't build systems to create distance between you and your customers or prospects. Let everyone else automate away their credibility. The company who stays clear and trustworthy will win the business."

⁠The urgency behind this, he argues, is only going to grow. The buyers of today are more skeptical than any generation before them. The buyers of tomorrow will be more skeptical still.

⁠"In ten years, Gen Z will be the decision makers. And you can say whatever you want about Gen Z, but they have a world-class BS detector. They've grown up in the age of AI. Videos that do well are shot on an iPhone, unedited, mistakes left in. That's a thirst for authenticity in a world that's so full of itself. These are the people who will be signing contracts for businesses in the next ten years."

⁠The buyer, he argues, has also fundamentally changed.

⁠The AI conversation is inseparable from a broader shift happening across the MSP market right now. Traditional helpdesk and per-user services are commoditizing fast. Margins are under pressure. And the way SMBs evaluate and buy IT services is changing in ways that most MSPs haven't caught up with yet.

⁠"Decision makers are polarizing into two camps. The ones who see us as a strategic lever and want a meaningful partnership, or the ones who see us as a high touch SaaS offering that can string all of their tech together. Both are right. You have to pick a camp and go all in."

⁠For MSPs still trying to sell the same way they did a decade ago, his message is direct.

⁠"If you keep showing up in a lime green polo talking about servers, you will be stuck in the server room forever."

⁠And for those willing to evolve, the opportunity is significant. Brian sees the MSP of the future not as a service provider but as something closer to a trusted guide, helping clients make sense of a technology landscape that is moving faster than most businesses can follow.

⁠"I want the MSP industry to be the safe harbor for entrepreneurs to come and decipher tech and AI hype. We should become the wizards who can dispel myths and build powerful systems. Help desk, customer support, and even SaaS will not exist in their current form in ten years. We must elevate to survive, and sales skills are the number one way to do that."

⁠Elevate or get left behind

⁠All of this, the AI disruption, the commoditization, the changing buyer, makes the sales conversation both harder and more important than it has ever been. For Brian, the answer to all of it lives in how you show up in that conversation.

⁠"The number one word is empathy. Number two is transparency. Stop thinking you're not allowed to get something from a sale in order for it to be a great idea for your prospect. Sales is not a win-lose. You can be transparent about what you get, while also being clear that it's worth it for the person. If you charge more money, explain it. Yeah, we make money on this. Of course you want us to make money, because you want us to be excited to talk to you, and you don't want us going out of business because we're losing money on your account. That's not in your best interest."

⁠Selling this way, he says, does something beyond closing more deals.

⁠"It's going to force you down a journey of personal growth. You're going to start identifying things in yourself that need to be resolved for you to go to the next level of your career."

⁠The MSPs who figure that out first, he believes, are the ones who will still be standing when everything else has been automated away.