The MSP Sales Podcast

Episode 50 - How Top MSPs Position vCISO Services (Guest: Erin McLean)

No mid-market CEO is waking up in a cold sweat hoping they can cut you a check for a list of cybersecurity frameworks and automated compliance reports.Most clients aren't looking for a "vCISO." They're looking for someone who can reduce risk, guide better decisions, and help them navigate an increasingly complex cybersecurity landscape.
The problem? Many MSPs are still selling technical expertise instead of business outcomes.
In this episode, Brian Gillette sits down with Erin McLean to explore how top MSPs position and sell vCISO services in a way that clients actually understand and value. They discuss why language matters, how to shift from technical conversations to strategic ones, and what it takes to become a trusted security advisor.
We cover: → How to position vCISO services as strategic business guidance → Common mistakes MSPs make when selling cybersecurity → How to communicate value without overwhelming prospects → What separates trusted advisors from the 
Whether you're launching a vCISO offering or refining an existing one, this episode will help you rethink how you position security, communicate value, and win more strategic client relationships.
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Learn more about Shawn via his 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
 

Episode 49 - Profiling and Tough Love: Rebuilding a Broken MSP Culture (Guest: Shawn Walsh)

There is a common problem that sabotages your client relationships.It is not your pricing.It is not your tech stack.It is you. Let me explain;
Most MSP owners blame turnover, blame difficult clients, blame the market.
Shawn Walsh did that too, until he lost three quarters of his tech staff in one week and watched them try to steal his customer list.
In this episode, Brian Gillette talks with Shawn Walsh, CEO of Encore Strategic and co-author of The Pumpkin Plan for MSPs.
Shawn built an MSP for 21 years, nearly destroyed it through his own leadership blind spots, then rebuilt it into a 400% growth story before exiting to private equity.
He breaks down the personality and EQ work that exposed why his team kept walking out, and how that same framework now helps other MSP owners spot the same patterns in themselves before it costs them their company. We cover;
→ Why undervaluing yourself shows up in pricing → Why raising your rates rarely costs you better clients→ How personality and EQ profiling exposes leadership blind spots→ How to tell if you are the common denominator in turnover→ Why communicating your vision mattersThis one is for MSP owners who suspect the problem might be closer to home than they want to admit.
 
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Learn more about Shawn via his 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

Episode 48 - 8 Visits a Day: One MSP Prospecting System That Actually Works (w/Guest: Aston Fortuna)

This episode is for the MSP sales rep who's exhausted every digital channel and doesn't know what to try next.
And for the MSP owner who handed someone a blank slate and said, "Figure it out."
MSPs are sending emails nobody opens and making calls that go straight to voicemail. Every inbox is flooded with the same templates, sequences, and cadences.
But Ashton Fortuna found a different path.
After transitioning from cable puller to Sales & Marketing Lead at Valley Tech Logic, Ashton had no sales training, no playbook, and no coach. Through trial and error, he built a prospecting system that now generates 50% of the company's new MRR through in-person canvassing - helping grow from two new clients a year to eight.
In this episode, we cover:
→ How Ashton targets businesses by industry and geographic radius→ Why the front desk is your greatest ally, not your biggest obstacle→ How AI maps and verifies prospects before you ever knock on the door→ How a part-time research VA can dramatically increase qualified visits
Brian also puts Ashton in the hot seat for a live pipeline coaching session, showing how a few small adjustments could double his results.
If you've been wondering what comes after cold email and cold calling, this episode gives you a practical prospecting system you can start adapting today.
 
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Learn more about Ashton via his 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
 

Episode 47 - The Algorithmic Approach to Booking Meetings for MSPs (Guest: Nicole Bielanski)

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.
 
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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
 

Episode 46 - Why Most MSPs Don't Know If They're Profitable (Guest: John Risko)

Most MSP owners think they know their numbers.The problem is... most don't.If you look under the hood of a stagnant MSP, the problem usually isn't sales.It's visibility. You can't improve profitability if you don't know where it's actually coming from. Many MSPs chase growth without understanding which customers, agreements, or services are making money. The result is more complexity, more work, and often very little improvement to the bottom line.
In this episode, Brian Gillette sits down with John Risko of MSP CFO & Accounting to unpack the connection between strategy, operations, and profitability. They discuss why specialization creates leverage, why many MSPs don't actually know their numbers, and how better visibility leads to better business decisions.We cover:
→ Why strategic focus matters more than adding revenue→ How saying "no" improves profitability→ The hidden cost of custom solutions→ Why many MSPs struggle to measure profit→ Ways to identify unprofitable customers…and more.
If you're trying to build a more profitable MSP, this conversation will challenge how you think about growth, metrics, and what it actually takes to scale.
Get in touch with today's guest, John Risko, at  www.MSPCFOandAccounting.com
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

Episode 45 - The MSP of the Future Will Be a vCISO (Guest: Jesse Miller)

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.
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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

Episode 44 - From Building to Closing: The Five Questions That Drive Revenue

Are you building a sales process or just avoiding doing the hard work?
A lot of MSP owners are stuck trying to build the perfect AI-powered Rube Goldberg machine. They want a system that sells for them. They obsess over tools, CRMs, and complex automations.
In this solo episode of The MSP Sales Podcast Brian Gillette breaks down why the exact skills that make you a great engineer are actively killing your sales numbers. He strips away the noise and brings it back to the five foundational questions you must answer before any marketing can work.
If nobody is buying your product it is time to sell a different product.
We cover: → The 5 fundamental questions every MSP must answer
→ How to repackage managed services as the foundation for AI adoption
→ Why you must clarify your positioning before you spend a dime on lead gen
If you are tired of overcomplicating your growth and want a straightforward path to closing deals this episode is for you.
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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
 

Episode 43 - The Cyber Insurance Shield: De-risking Your MSP (w/Guest: Andy Runyan)

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.
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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
 

Episode 42 - Stop Acting Like Spam: An MSP Guide to Cold Email (w/Guest: Brian Kelly)

Most MSPs think cold email stopped working.
The reality?
Most outbound campaigns fail before anyone even reads the message.
In this episode, Brian Kelly breaks down why deliverability has become the real bottleneck in MSP marketing, and why most providers are still approaching outbound the wrong way.
Brian shares how he applied a technical, engineering mindset to sales and built systems focused on one core principle:
“The best way to avoid being treated like spam is to stop acting like spam.”
We cover:
→ Why most MSP emails never reach the inbox→ The real impact of AI on outbound marketing→ The role of context, timing, and relevance in outbound→ How MSPs are doing the right things in the wrong order
If your outbound strategy feels inconsistent, overcomplicated, or ineffective, this episode will challenge a lot of assumptions.
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Learn more about Brian Kelly's services at Automated MSP - an MSP-native AI-powered outbound prospecting platform that helps managed service providers generate qualified leads, recruit talent, build strategic partnerships, and identify opportunities via cold email automation.
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

Episode 41 - How I'd start an MSP in 2026

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.
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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