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PODCAST

The MSP Sales Podcast

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

technology

All Episodes

65:17

Episode 23 - How One MSP Owner’s Sales Shift Grew...

The MSP Sales Podcast ·

2025/09/15

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

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51:16

Episode 22 - How MSPs Build Sales Confidence (w/...

The MSP Sales Podcast ·

2025/09/01

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

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40:29

Episode 21 - Chaos to Clarity: Streamlining MSP...

The MSP Sales Podcast ·

2025/08/18

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

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01:01:41

Episode 20 - The Sales Fixation That’s Failing MSPs

The MSP Sales Podcast ·

2025/08/04

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

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01:09:31

Episode 19 - Cold Outreach That Actually Works

The MSP Sales Podcast ·

2025/07/21

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

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20:59

Episode 18 - Stop Killing Your Own Opportunities

The MSP Sales Podcast ·

2025/07/07

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

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54:44

Episode 17 - Stop Winging It, Start Winning

The MSP Sales Podcast ·

2025/06/23

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

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20:58

Episode 16 - The Only Way Out Is Through

The MSP Sales Podcast ·

2025/06/09

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

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54:43

Episode 15 - From Tech Geek to Trusted Seller with...

The MSP Sales Podcast ·

2025/05/26

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

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01:30:38

Episode 14 - Rebuilding the Business You Actually...

The MSP Sales Podcast ·

2025/05/12

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 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

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01:05:37

Episode 13 - The Truth About Leads and Growth

The MSP Sales Podcast ·

2025/04/28

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

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39:30

Episode 12 - Authentic MSP Marketing in a Skeptical...

The MSP Sales Podcast ·

2025/04/10

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

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41:19

Episode 11 - SaaS vs. MSP Sales: What Works and What...

The MSP Sales Podcast ·

2025/03/27

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

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42:46

Episode 10 - Fixing MSP Sales: A Forensic Approach

The MSP Sales Podcast ·

2025/03/13

More reps, more tools, more activity - does that result in more sales? Not always. Your pipeline might even be full, but the deals just aren’t closing. In this episode, Brian Gillette sits down with Jeffrey Newton, former MSP sales leader turned co-founder at Cyft, to break down a forensic approach to diagnose and fix sales inefficiencies. They discuss why process alone isn’t enough and how aligning human connection with sales strategy is what truly leads to growth. They'll discuss; Why

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37:14

Episode 9 - Stop Being a Commodity

The MSP Sales Podcast ·

2025/02/17

Are you tired of drifting along in a sea of sameness? In this episode of The MSP Sales Podcast, Brian Gillette sits down with Alex Farling to talk about one of the biggest challenges in the managed services industry - standing out in a crowded market.This episode breaks down how MSPs may unknowingly commoditize themselves, and struggle to communicate their unique value. From refining your sales process to creating deeper client relationships, Alex shares hard-hitting insights that can steer your

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40:45

Episode 8 - Why Marketing Should Start with Strategy

The MSP Sales Podcast ·

2025/01/31

In this episode of 'The MSP Sales Podcast,' host Brian Gillette sits down with Tim Fitzpatrick of Rialto Marketing to uncover the critical overlap between sales and marketing for MSPs. They look at why many MSPs struggle with lead generation and the importance of setting a clear strategy before diving into marketing initiatives. Tim shares his insights on how to verticalize your services, build trust through targeted messaging, and ensure long-term business success. Are your marketing efforts

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45:28

Episode 7 - Keys to MSP Sales Team Success

The MSP Sales Podcast ·

2025/01/15

In this episode of The MSP Sales Podcast, Brian Gillette chats with Casey Seaborne about how MSPs can transform their MSP sales teams success and scalability. Casey shares actionable insights on why sales processes often fail, the role of emotional intelligence (EQ) in sales success, and the steps MSP owners need to take to support their sales teams effectively.Casey explains how simplifying offerings, standardizing processes, and focusing on outcomes rather than just features can create a more

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45:07

Episode 6 - Do It Right, Do It Well, Do It Over:...

The MSP Sales Podcast ·

2024/12/19

Want to scale your MSP? Join Brian Gillette and John Davenjay of Bowman Williams as they discuss the secrets of how to hire right and staff your MSP both successfully and effectively. With lessons drawn from John’s inspiring journey - this episode is packed with practical advice to help you take your business to the next level.John shares how grit and determination helped shape his career, battling through challenges as an entrepreneur and learning how to replicate success. Whether you’re

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01:06:51

Episode 5 - Transactional to Transformational...

The MSP Sales Podcast ·

2024/12/02

Opportunities don’t always come gift-wrapped - and MSPs who learn to spot them win out. In this episode of The MSP Sales Podcast, Brian Gillette sits down with Kevin Clune of MSP Growth Hacks ( https://www.MSPGrowthHacks.com ) to explore how to transform transactional thinking into meaningful, long-term partnerships.From creating value in unexpected ways to leveraging client relationships for referral growth, this conversation is packed with real-world stories and actionable advice. Learn how to

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29:02

Episode 4 - Good, Great, or the Best?

The MSP Sales Podcast ·

2024/10/31

In this episode of the Feel-Good MSP Podcast, Brian Gillette challenges you to think deeply about your career aspirations. Do you want to be good, great, or the best in your field? Brian breaks down the pros, cons, and hard truths of each level and what it takes to reach the top.Using real-world sales examples, we explore how good salespeople achieve their goals, build reputations over time, and strike a balance between work and life. But is that enough to push your MSP to the next level? What

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