The MSP Sales Podcast

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 tr...

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 ...

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, transi...

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 “pe...

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-minde...

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...

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 s...

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 relyi...

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 ...

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 str...

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 re...

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, an...

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...

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 entrepr...

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 ...

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 l...

In this episode of the MSP Sales Podcast, Brian Gillette is joined by Taher Hamid of MSP Camp to discuss how Managed Service Providers can leverage specific types of marketing content to attract leads, build trust, and close more deals. We'll explore the role of content in MSP growth, from building brand authority to creating engaging sales narratives that convert.

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In our second episode of The MSP Sales Podcast, your host Brian Gillette, and special guest Robert Gillette (MSP Dojo) explore the reasons why sales training often fails for Managed Service Providers. Together they discuss the various factors that affect the effectiveness of sales training, and how your MSP can step up to face the change and discomfort that often come right alongside sales growth. More than just the latest sales te...

In our first episode of The MSP Sales Podcast, your host Brian Gillette dives into the discomfort many business owners feel about selling managed IT services. We explore why selling managed services can feel unnatural and why it seems like prospects are becoming more difficult to reach and trust harder to establish. How does the "Adversarial Sales Complex" impact both buyers and sellers? Brian explains this phenomenon and how you c...