The MSP Sales Podcast

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

Mon, 14 Sep 2026 06:00:00 -0700

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.

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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
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#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

Episode 58 - How to Break the Ice at Your Next Networking Event

Mon, 07 Sep 2026 06:16:39 -0700

You walk into a networking event and start selling.
That is the fastest way to leave with nothing.

MSPs treat these rooms like a numbers game, pitching everyone and hoping something sticks.
People feel the agenda and shut down before you finish your sentence.

In this solo episode, Brian breaks down how he actually breaks the ice, at events and on cold calls.
The reframe: you are not there to close.
You are there to earn a second conversation.

→ Invite yourself into a conversation circle instead of hovering
→ Ask two or three follow up questions before you pitch anything
→ Run cold calls on three things: your objective, your motive, how they win

This one is for any MSP owner who dreads walking into a room full of strangers.
Walk out with the confidence to break the ice and build warm pipeline.

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Interested in attending ScaleCon 2026? Register here with code FeelGood50 for a $50 discount: https://cvent.me/e9BBxL

Episode 57 - Fire Fast, Grow Faster: Taher Hamid's Team-Building Playbook (w/ Taher Hamid)

Mon, 31 Aug 2026 06:18:36 -0700

If you look under the hood of a stalled MSP, you rarely find a bad market.
You find one lead source, one excuse, and zero accountability.

Most owners want one channel to save them.
When SEO does not hit in three months, they blame the tactic.
When leads come in and they cannot close, they blame the agency.

Taher Hamid is back on the podcast - our first repeat guest!
He runs MSP Camp, the Apex agency, and the ScaleCon conference.
He and Brian break down why growth ceilings are almost always self-imposed. Not the market. Not the vendor. The owner.

→ Give SEO and AEO twelve months before you judge the channel
→ Run several lead sources at once, never rely on one snare
→ Fire fast when someone cannot keep pace with the team's standards

This one is for MSP owners waiting on one channel or one hire to fix their growth.
You’ll walk away knowing exactly where your ceiling comes from.

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Interested in attending ScaleCon 2026? Register here with code FeelGood50 for a $50 discount.
Learn more about Taher Hamid 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

Episode 56 - What One Man Can Do: Rebuilding an MSP After Losing It All (w/ Sergey Poltev)

Mon, 24 Aug 2026 06:00:00 -0700

If you look under the hood of an MSP that never grows, you will usually find one owner trying to do it all. That was Sergey Poltev, and it almost cost him everything.

He was overworked, stuck in the tickets, and running his life on empty. The burnout cost him his marriage and his house. Then, a bad partnership deal collapsed and cost him half of his clients, leaving him with barely enough to survive.

If you are an MSP owner, there is guaranteed to be something you can relate to in Sergey's story. He is a computer science grad who had to learn the hard way that a technical ego is the ultimate bottleneck to business freedom.

He rebuilt from absolute scratch by shifting his entire operational philosophy. Instead of micromanaging tasks, he started delegating by outcomes. Today, he runs two multi-million dollar MSPs and a global virtual staffing agency. He breaks down how he let go, why virtual talent is the cheat code for scaling, and how pairing AI with a VA multiplies your leverage.

We cover:

→ Why most owners hand their team tasks instead of outcomes
→ Why you must treat offshore talent like full employees
→ How to do a proper "time study" to figure out what only you can do
→ Rejection proofing: How a stand-up comedy course can fix your sales

Whether you are drowning in tickets or trying to make your first hire, Sergey's story shows what is waiting on the other side of letting go.

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Learn more about Sergey Poltev via his LinkedIn.

Episode 55 - These Six Sales Myths are Killing Your Results

Mon, 17 Aug 2026 06:00:00 -0700

If you look under the hood of a stalled MSP sales process, you'll usually find the same six pieces of advice.
Advice that sounds right.
Advice that's been recycled from forum posts and LinkedIn threads until nobody remembers where it came from.

Most MSPs never test it.
They just repeat it, and it slowly caps their growth.

In this solo episode, Brian pulls apart six sales myths making the rounds in the MSP space right now.

This one's for any MSP owner who's been quietly following advice they never actually stress-tested.

Walk away knowing which of these six myths have been sitting in your sales process, and what to do instead.

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Episode 54 - Overthinking to Clarity: Life Engineering for MSP Owners (w/ Gabriela Embon)

Mon, 10 Aug 2026 06:00:00 -0700

If you look under the hood of a stagnant MSP, you will find a dysregulated owner.

Not a broken sales process.

Not a bad tech stack.

MSP owners carry a level of pressure that shows up on their faces, in their bodies, and inside their teams.

When stress goes unmanaged, it does not stay at the office.

It drives micromanagement, fractures relationships at home, and builds a team that depends on you instead of functioning without you.

Treating work and life as two competing forces makes it worse.

Gabriela Embon is a certified professional coach and chemical engineer who was sought out by MSP conference leaders because of one pattern they kept seeing: personal dysregulation is an epidemic in the channel, and it is costing operators more than they realize.

In this episode, she reframes the work-life balance myth, explains why connection is the most underused performance tool in an MSP owner's toolkit, and walks through a practical transition protocol that anyone can start using today.
We discuss how:

→ Overthinking is a coping mechanism for lack of trust

→ Work-life balance creates two competing forces.

→ When you come home dysregulated, you micromanage, disempower your team, and build dependency

→ Connection, not distance, is what actually regulates your stress

→ Tiny, intentional steps compound

This episode is for the MSP owner who knows stress is affecting their performance but does not know where to start.

You will walk away with a a reframe, and a reason to take the first step.

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Learn more about Gabriela Embon via her website.

Episode 53 - 7 MSP Investments to Make Before Marketing

Mon, 03 Aug 2026 06:00:00 -0700

If you look under the hood of a stalled MSP pipeline, the wiring problem usually isn't marketing.
It's everything sitting underneath it.

Ads and outbound only work as well as the foundation holding them up.
Bad lighting on a sales call, no real CRM, no owned data list. These quietly cap what any campaign can do.

In this solo episode, Brian Gillette walks through seven investments, each under $1,000, that build trust and confidence before a single pitch happens.
None of it is more marketing spend. It's what marketing can't fix on its own.

For MSP owners frustrated with their numbers and ready to look underneath the marketing,
this episode is seven concrete, sub-$1,000 moves you can make this month.

** Access the link mentioned in this episode http://feelgoodmsp.com/apollo

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This episode is seven concrete, sub-$1,000 moves you can make this month.

Episode 52 - Money Treadmill: Why Working Harder Never Builds MSP Wealth (w/ Justin D Maxwell)

Mon, 27 Jul 2026 06:00:00 -0700

Revenue can climb for a decade.
Net worth can stay flat the whole time.
That gap is where most MSP owners get stuck.

Standard financial advice is built for salaried employees. Save a percentage, invest a percentage, wait for retirement. That breaks down when your income comes from a business and swings by six figures a year.

Justin D Maxwell has worked one-on-one with close to 1,000 seven-figure earners on this problem. He joins Brian to unpack the difference between money and wealth, and how a family office model turns profit into a system instead of a guess.

→ Why money and wealth are not the same thing
→ How a scarcity number mindset keeps high earners stuck
→ The shift from comfort driven thinking to impact driven wealth
→ Using the Ansoff Matrix to decide: push your current market, or expand
→ Why partnering before buying lowers the risk of a new market
→ Applying poker's estimated value thinking to marketing decisions
→ The two mistakes that keep profitable owners from building real wealth

This episode is for MSP owners making money that never turns into anything lasting. Justin lays out a deliberate way to turn profit into wealth.

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Learn more about Adam via his website.

Episode 51 - Foot in the Door, Not a Doormat: How to Win Mid-Market MSP Deals (w/ Adam Burke)

Mon, 20 Jul 2026 06:00:00 -0700

There is a quiet mistake sabotaging your biggest mid-market deals.
It is how you price the first project.

Most MSPs chase the big RFP.
Five hundred users, full boat, the whole suite.
It looks like the dream deal.
It is actually a bloody knife fight, and you only see three of the ten ways to lose it.

Adam Burke is VP of Sales and Partnerships at Quest, one of the largest MSPs in the country.
He skips the RFP fight.
He wins mid-market accounts by landing a small project first, then earning the bigger contract on trust.

→ Why full-boat RFPs are a losing bet for most MSPs
→ How one small entry project, like a single DBA fix, becomes the door to a bigger contract
→ Why foot-in-the-door pricing and a foot-in-the-door project are not the same thing
→ The four buckets every client rotates through, and how to sell into each one
→ Why you never price a contract on hope or on loyalty
→ Why flattery is more dangerous to a growing MSP than honest criticism

This one is for MSPs still trying to win by outbidding everyone on the big deal.
Land small, prove yourself, then get paid full price for the second job.

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Learn more about Adam via his LinkedIn.

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

Mon, 13 Jul 2026 06:00:00 -0700

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 Erin via his LinkedIn.

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

Mon, 06 Jul 2026 06:00:00 -0700

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 matters

This 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.

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

Mon, 29 Jun 2026 06:00:00 -0700

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.

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

Mon, 22 Jun 2026 06:00:00 -0700

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.

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

Mon, 15 Jun 2026 08:00:00 -0700

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

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

Mon, 08 Jun 2026 08:14:38 -0700

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.

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

Mon, 01 Jun 2026 06:00:00 -0700

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

Mon, 25 May 2026 06:00:00 -0700

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.com
Learn 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
.

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

Mon, 18 May 2026 03:00:00 -0700

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.

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

Mon, 11 May 2026 06:00:00 -0700

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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Episode 40 - Why Most MSPs Get Compliance Completely Wrong (w/Guest: Tim Golden)

Mon, 04 May 2026 06:00:00 -0700

Most MSPs get compliance completely wrong.

They treat it like a product.
They overcomplicate it.
Or they try to charge a premium for something they can’t clearly define.

In this episode, Tim Golden (Founder and CEO of Compliance Scorecard) breaks down what compliance actually is - and how MSPs should be using it.

→ Why compliance is a process, not a tool
→ How to position yourself as a facilitator, not just a fixer
→ The simple framework for delivering compliance without complexity
→ How compliance uncovers gaps that turn into real revenue

This isn’t about adding another service.

It’s about changing how you think about value, risk, and your role in the client relationship.

If you’re trying to move upstream, get a seat at the table, and stop being seen as “just IT” - this is the shift.

Looking for Tim's FTC Safeguards CaaS Facilitation Workflow Document (mentioned in the episode) ? Get it here.
It's a practical playbook to help Managed Service Providers (MSPs) guide small and midsize businesses through the legal requirements of the FTC Safeguards Rule (16 CFR 314.4).

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Episode 39 - Is SaaS Replacing the Traditional MSP? (w/Guest: Omar Armenteros)

Mon, 27 Apr 2026 06:00:00 -0700

In this episode, Brian Gillette talks with Omar Armenteros, CEO and founder of Virtuworks, about the future of managed services and how SaaS is changing the game. With over 30 years in the industry, Omar shares how his company shifted from traditional break-fix models to software-driven solutions that scale and automate to meet today’s demands.

They discuss how this change is reshaping the way MSPs operate, why automation is essential for growth, and how customer expectations are evolving. Omar also explains why the traditional MSP model is fading, making way for a new, software-centric approach to IT services.

In this episode, you’ll learn:

How Virtuworks adopted SaaS to improve operations
The importance of meeting changing customer expectations in 2026
Why automation is crucial for growing an MSP business
How to adapt to the shift from service to software

Listen in to hear how the managed services landscape is evolving, and why embracing software might be the key to staying ahead.

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Episode 38 - Relax, Focus, Succeed: Karl Palachuk's Journey in Managed Services

Mon, 13 Apr 2026 06:00:00 -0700

In this episode, Brian Gillette speaks with Karl Palachuk, a prolific author and two-time MSP business owner, about his journey in the managed services industry. With over 25 books under his belt, Karl delves into his philosophy on success, focusing on relaxation, focus, and sustainable growth.

Karl also reflects on his battle with health challenges and how they influenced his approach to business and life. He shares how he transformed from focusing solely on hard work to understanding the importance of balance and focus. The discussion moves into the evolving managed services landscape and why MSPs must adapt to stay relevant.

In this episode, you’ll learn:

How relaxation and focus lead to success
Why work-life balance isn’t a myth, but a necessary pursuit for MSP owners
The shift in managed services towards solving bigger business problems
Insights from Karl's success in building and selling MSPs

Tune in to gain valuable advice on balancing business growth, personal health, and staying ahead in the fast-paced MSP world.

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Episode 37 - Your MSP Will Only Grow as Fast as You Do, Here’s Why (w/Guest: Paul Vedder)

Mon, 30 Mar 2026 06:00:00 -0700

What does personal growth have to do with business success? A lot! Join Brian Gillette and Paul Vedder, CEO of VXIT, as they dive into how overcoming personal challenges fueled his professional achievements. In this raw, honest conversation, Paul shares the pivotal moments when shifting his mindset and committing to physical fitness reshaped not only his life but his MSP business.

Paul opens up about his journey - from battling addiction to becoming a marathon runner - and how these personal victories directly translated into business triumphs at VXIT. Learn how small daily habits and a commitment to self-improvement are the key to sustainable business growth.

In this episode, you’ll learn:

The personal habits that lead to professional success
How your health can supercharge your business
Why overcoming personal limitations is essential
How to build a thriving business with the right mindset

Don’t miss this inspiring conversation about the power of personal growth in business success.

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BONUS Episode - A New Sales System for 6-Figure MSPs

Mon, 23 Mar 2026 06:00:00 -0700

This is a bonus episode - and a different one.

If you’re here for a standard interview or tactical breakdown, feel free to skip this one. We’ll be back with a regular episode next week.

But if you’re an MSP owner who’s been following the podcast and thinking, “This makes sense, but I’m not ready for a full coaching program yet” - this is for you.

In this episode, Brian introduces MSP Sales Foundations - a new, self-serve membership designed specifically for six-figure MSPs who want to build a real sales engine without the time or financial commitment of 1:1 coaching.

This is built for MSPs who need to fit sales into a busy schedule - and want a clear, practical system to generate consistent growth.

Get notified when it's available and an invite to our online launch party: https://go.feelgoodmsp.com/msp-sales-foundations

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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.com

Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", has just been released in 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
.

Episode 36 - The 3 Things Every MSP Needs to Grow (w/Guest: Tim Conkle)

Mon, 16 Mar 2026 06:00:00 -0700

Most MSPs don’t fail because of technology.

They stall because the fundamentals of growth aren’t in place.

In Episode 36 of The MSP Sales Podcast, Brian Gillette is joined by Tim Conkle to break down the three foundational elements every MSP needs if they want to scale beyond survival mode.

This conversation dives into what separates MSPs that plateau from those that build real momentum - and why many owners focus on tactics before these core pieces are actually in place.

In this episode, you’ll hear:

→ The 3 foundational ingredients every growing MSP needs
→ Why leadership maturity determines the ceiling of your business
→ Why sales and marketing discipline matters more than tools

If your MSP feels stuck, overwhelmed, or inconsistent in growth, this episode explains what needs to change first.

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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.com

Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", has just been released in 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
.

Episode 35 - From MSP Operator to Visionary CEO (w/Guest: Shawn Freeman)

Mon, 02 Mar 2026 06:28:29 -0800

Most MSP owners don’t struggle because they lack technical skill.
They struggle because they’re stuck operating instead of leading.

In Episode 35 of The MSP Sales Podcast, Brian sits down with serial entrepreneur and MSP growth strategist Shawn Freeman to unpack what it really takes to transition from hands-on operator to visionary CEO.

This isn’t theory. It’s about building scalable systems, integrating AI intentionally, and shifting your leadership identity so the business can grow beyond you.

In this episode, you’ll hear:

→ Why MSP owners stall when they stay in operator mode
→ How AI and automation should actually be integrated into your firm
→ The leadership shift required to build something scalable
→ What resilient, future-ready MSPs are doing differently

If you want to stop being the bottleneck and start building an MSP that scales with intention, this episode lays out the path.

_____________________________________________________

Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com

Recent News:
Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", has just been released in 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
.

Episode 34 - Not All Good Advice Is Good For You

Mon, 16 Feb 2026 06:00:00 -0800

In Episode 34 of The MSP Sales Podcast, Brian Gillette breaks down a hard truth. Most MSP owners learn the expensive way: not all “good advice” is good for you - at least not yet.

Some advice is universal. Some is contextual. And some is only true in a specific sequence, after certain prerequisites have been put into place.

In this episode, you’ll learn:
→ The 3 types of advice (and how to spot the difference)
→ Why “proven tactics” fail when your MSP is in the wrong stage
→ How MSPs waste money on PPC, lead gen, and automation too early
→ Why hiring sales reps before your sales process is repeatable backfires

If you’ve ever felt like you’re doing everything you’re told and still not seeing results, this episode will help you identify what’s missing: context, stage, and order.

_____________________________________________________

Episode 33 - The Webinar Framework: Build a 24/7 Lead Gen Machine (w/ Guest: Scott Millar)

Mon, 02 Feb 2026 06:00:00 -0800

Word-of-mouth is the lifeblood of the MSP, but it is notoriously difficult to scale. In this episode, Brian Gillette sits down with Scott Millar (IT Rockstars), author of Virtually Irresistible, to discuss why webinars are the ultimate bridge between technical expertise and scalable relationship building.

Many MSP owners avoid webinars due to "tech anxiety" or a fear of public speaking, but Scott reframes the process as a repeatable system rather than a performance. They dive deep into the tactical side of lead generation, explaining why Meta’s machine learning often outperforms LinkedIn for reaching decision-makers at a fraction of the cost.

In this episode, you’ll learn:

Why "dog whistle" copy is the key to attracting your ideal client profile
How to overcome camera shyness by acting as a "guest expert"
The technical "minimum viable process": Why audio quality matters most
To upcycle one 40-minute webinar into two months of social media authority

This episode provides the structural blueprint to move from accidental 'word-of-mouth' growth to an intentional, scalable inbound system.

_____________________________________________________

Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", has just been released in 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

Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com
.

Episode 32 - From Survival to Scale: An MSP Growth Story (w/Guests: John Snyder & Neelesh Patel)

Mon, 19 Jan 2026 06:02:12 -0800

In Episode 32 of The MSP Sales Podcast, Brian Gillette is joined by John Snyder (CEO) and Neelesh Patel (President) of Net Friends for a candid, behind-the-scenes look at what it really takes to build a successful MSP - the wins, the mistakes, and the decisions that shaped where they are today.

This isn’t a polished success story. It’s an honest conversation about growth through constraint, learning the hard way, and how a strong partnership became a competitive advantage instead of a liability. John and Neelesh share how they navigated leadership challenges, clarified roles, and built trust as the company scaled.

Along the way, they dig into how Net Friends thinks about marketing, differentiation, and experimentation. This episode is packed with insights MSP owners can actually apply.

In this episode, you’ll hear:
➡️ How a strong CEO–President partnership accelerates growth
➡️ The mistakes they made early - and what they’d do differently
➡️ Why clarity of roles matters more as MSPs scale
➡️ Creative marketing and AI ideas

If you’re an MSP who wants to learn from people who’ve lived it - this episode offers a look at what sustainable success requires.

_____________________________________________________

Episode 31 - Reactive to Intentional: How MSP Leaders Actually Level Up (w/ Guest: Chris Day)

Mon, 05 Jan 2026 06:00:00 -0800

In Episode 31 of The MSP Sales Podcast, Brian Gillette is joined by Chris Day (CEO at ScalePad) for a no-nonsense conversation about the shift every MSP leader must make to move from reactive survival mode to intentional leadership.

Too many MSPs remain dependent on the owner. Every decision, escalation, and bottleneck runs through one person. Chris breaks down why this happens, how it silently limits momentum, and what it actually takes to build an MSP that can operate and grow without constant founder involvement.

Together, Brian and Chris explore:
➡️ Why reactivity keeps MSPs stuck (even when revenue is growing)
➡️ How intentional leadership creates leverage
➡️ How to build systems instead of dependencies
➡️ How to step out of the day-to-day without losing control of the business

If you’re an MSP owner who feels indispensable to your business - or concerned that your growth still feels fragile - this episode will challenge how you think about what “leveling up” looks like.

_____________________________________________________

Have you heard the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)"
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

Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com

#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining

Episode 30 - Building the Modern MSP: AI, Cloud & UX (w/ Guest: Jim Spignardo)

Mon, 22 Dec 2025 06:00:00 -0800

In Episode 30 of The MSP Sales Podcast, Brian Gillette sits down with Jim Spignardo, Director of Cloud Strategy & AI Enablement at ProArch, for a practical conversation about what it actually takes to build a modern MSP today.

With over 25 years in IT across networking, cloud, cybersecurity, and consulting, Jim brings a grounded perspective on how MSPs must evolve beyond tools and tech stacks. Together, they explore how cloud maturity, AI enablement, and user experience now intersect - and how ignoring any of them creates friction for clients and internal teams.

They discuss;
➡️ Why “modern MSP” is more about experience than tech
➡️ How AI is reshaping service delivery
➡️ The role of cloud strategy in long-term MSP relevance
➡️ Why UX matters just as much for internal teams as end users
➡️ Common mistakes MSPs make when adopting AI

If you’re an MSP owner, technical leader, or consultant trying to modernize your services, this conversation will help you think more clearly about where to focus.

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Episode 29 - Selling Cybersecurity Without Fear In The AI Era (w/ Guest: Dor Eisner)

Mon, 08 Dec 2025 06:00:00 -0800

In Episode 29 of The MSP Sales Podcast, Brian Gillette sits down with Dor Eisner (CEO & Co-Founder of Guardz) for a grounded, myth-busting conversation about selling cybersecurity in an AI-shaped world.

Too many MSPs feel pressured to become “cyber experts” overnight while many clients think cybersecurity is either too technical or too expensive to take seriously. Dor explains why both sides are looking at the problem the wrong way, and how MSPs can simplify, educate, and lead with confidence.

Together, they explore:

➡️ Why MSPs overestimate how much clients want to know about cybersecurity
➡️ How AI is already reshaping threat landscapes
➡️ A practical path for MSPs who feel “outgunned” by the pace of innovation
➡️ Why selling cybersecurity is really about risk reduction
➡️ The common fears that stall customer decisions

Whether you’re an MSP owner, vCISO, or someone trying to meaningfully add cybersecurity to your stack, this episode will help you communicate value more clearly, close deals more confidently, and protect clients more effectively.

_____________________________________________________

Have you heard the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)"
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

Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com

#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing

Episode 28 - Profitable Packaging: Fueling Predictable Growth (w/ Guest: Brian Hoppe)

Mon, 24 Nov 2025 06:00:00 -0800

In Episode 28 of The MSP Sales Podcast, Brian Gillette sits down with Brian Hoppe (Strategic Advisor and Revenue Coach to MSPs) to unpack why pricing, packaging, and financial clarity shape the entire sales experience. Not through pressure, scripts, or gimmicks - but through alignment, transparency, and knowing your numbers.

Together, they break down how the right packaging eliminates discounting, creates confidence in the sales process, and makes growth predictable instead of stressful.

In this episode, you’ll learn:
➡️ How unclear packaging causes stalled deals and endless discounting
➡️ What finance numbers you must understand before you scale
➡️ The link between accountability, pricing, and recurring revenue
➡️ How your pricing model shapes your sales culture (for better or worse)
➡️ What good forecasting and predictable revenue look like inside an MSP

This isn’t a conversation about “raising prices.” It’s a conversation about building a sales-ready business, one where your team can confidently sell, your clients know exactly what they’re paying for, and your growth becomes predictable instead of stressful.

_____________________________________________________

Did you catch the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)"
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

Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com

#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing

Episode 27 - Lead Generation for MSPs: What Actually Works

Mon, 10 Nov 2025 06:00:00 -0800

In Episode 27 of The MSP Sales Podcast, Brian Gillette kicks off the new Lead Generation Series- a focused, no-nonsense deep dive into what actually works for MSPs looking to build a reliable pipeline.

Don’t waste time on the gimmicks, shortcuts, and “one weird trick” advice floating around out there. This episode breaks down the fundamentals of consistent outbound lead generation - how to use calls, emails, and events in a repeatable, measurable way to drive sales conversations.

Want to know what separates MSPs who get consistent leads from those who stay stuck in “feast or famine” mode? Learn;
➡️ The truth about why most outbound fails
➡️ How to balance short-term outreach with long-term brand building
➡️ What to measure (and what not to obsess over)

If you’ve ever wondered why your lead gen feels unpredictable, this episode lays the foundation for this series. Because real growth doesn’t come from hacks. It comes from doing the right work, consistently.

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"How To Sell a Sh*tload of Managed Services (without selling your soul)" <--- A new book now available at Amazon.
Written by Brian Gillette, Founder of Feel-Good MSP and host of the MSP Sales Podcast - it’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values.
Get it now https://a.co/d/hJKoFxg

Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com

#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #MSPLeadGen #LeadGeneratio #LeadGen

Episode 26 - Lessons from Building, Selling, and Starting Over (w/ Guest: Colin Knox)

Mon, 27 Oct 2025 06:19:45 -0700

What do you do after you’ve reached the top?
You’ve achieved the dream - built the business, and made the exit.
The pressure’s gone, and the question becomes - what now?

In Episode 26 of The MSP Sales Podcast, Brian Gillette sits down with Colin Knox (Founder of Gradient MSP, Passportal, & MSPCentric) for a conversation that gets down to the realities of entrepreneurship — what drives us, what drains us, and what’s waiting on the other side of “making it.”

Colin opens up about his own journey and shares hard-earned lessons from building, selling, and starting over — including:
➡️ Why chasing money rarely leads to fulfillment
➡️ How to define success beyond the spreadsheet
➡️ Why impact and purpose are stronger motivators than profit

If you’ve ever wondered what separates “busy” from “fulfilled,” or what happens after the big win, this episode is the one.

Because sometimes, the real work begins after you’ve already “made it.”

_____________________________________________________

Did you catch the news about Brian's new book? "How To Sell a Sh*tload of Managed Services (without selling your soul)"
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

Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com

You can reach our guest Colin Knox on LinkedIn.

#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing

Episode 25 - Marketing Works. Yours Doesn’t. Here’s Why. (w/ Guest: Johnathan Schofield)

Mon, 13 Oct 2025 07:08:16 -0700

Too many MSPs are still waiting for someone else to grow their business for them. In Episode 25 of The MSP Sales Podcast, Brian Gillette sits down with Johnathan “Skofi” Schofield, founder of FindMyITPartner.com, to unpack why so many MSPs feel stuck when it comes to growth. They break down why 77% of MSPs still rely on referrals, and what MPSs can do to start building trust on purpose instead of waiting for it to happen.

They dig into the truth behind MSP marketing:
➡️ Why “marketing doesn’t work for MSPs” is a myth
➡️ How consistency beats complexity every time
➡️ Why referrals aren’t a growth strategy (and what to do instead)
➡️ How to manufacture trust before a prospect even talks to you

This one’s a practical look at what it really takes to turn activity into traction.
Because marketing works. Sales works.
The only question is: are you working it?

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#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing

Episode 24 - Standing Out in a Sea of MSP Sameness (w/ Guest: Paul Green)

Mon, 29 Sep 2025 06:20:53 -0700

In Episode 24 of The MSP Sales Podcast, Brian Gillette sits down with Paul Green — one of the most respected voices in the MSP community — to unpack why so much MSP marketing looks the same and how to finally break free.

When every website, offer, and stock photo blends together, it’s harder than ever for prospects to tell you apart. Paul shares practical, battle-tested ways to brand yourself more authentically and make your marketing unmistakably yours:

➡️ Put your name and face front and center to build real trust
➡️ Create authentic content (even on a small budget)
➡️ Avoid “AI slop” - human stories always beat generic copy
➡️ Build charisma and confidence, even if you’re introverted

If your campaigns feel invisible or prospects ghost you after the first touch, this episode will show you how to stand out, connect more deeply and become the MSP people actually remember.

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Episode 23 - How One MSP Owner’s Sales Shift Grew $70K in MRR (w/ Guest: Craig Bell)

Mon, 15 Sep 2025 06:00:00 -0700

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 confidence
✅ How training, coaching, and process changes can accelerate growth
✅ The practical steps that turned sales from stressful to sustainable

If you’ve ever felt stuck chasing the wrong leads, struggling to move deals forward, or doubting your ability to sell, this conversation is for you.

Tune in and learn how to rebuild your MSP sales process from the ground up.

_____________________________________________________

Rebuild your MSP sales process from the ground up with www.FeelGoodMSP.com

#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth

Episode 22 - How MSPs Build Sales Confidence (w/ Guest: Brian Doyle)

Mon, 01 Sep 2025 07:03:13 -0700

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 process are the antidotes to hesitation, and how MSPs can turn self-doubt into steady confidence.

You’ll discover:
✅ How reframing sales as helping changes everything
✅ Why process, preparation, and practice eliminate fear
✅ Practical ways MSPs can build lasting confidence

If sales still feels uncomfortable, this episode is your playbook for breaking free from imposter syndrome - and winning with confidence.

_____________________________________________________

Your next level of MSP sales starts at www.FeelGoodMSP.com
Learn more about vCIO Toolbox at https://vciotoolbox.com

Episode 21 - Chaos to Clarity: Streamlining MSP Operations for Growth (w/ Guest: Ash Welsh)

Mon, 18 Aug 2025 09:44:00 -0700

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 change management needs during staff turnover

✅ Streamline and simplify processes so they’re easy to understand and communicate

Whether you’re the CEO or a frontline team member, the ability to think critically about how you work — and how you can do it better — will directly impact your efficiency, profitability, and client experience. This episode offers actionable ideas you can put into practice right away.
_____________________________________________________

Learn to rebuild your MSP sales process from the ground up at www.FeelGoodMSP.com
Learn more about Quoter at https://www.scalepad.com/quoter/

#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth

Episode 20 - The Sales Fixation That’s Failing MSPs (w/ Guest: Wes Spencer)

Mon, 04 Aug 2025 06:40:00 -0700

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 providers struggle with growth, not because they lack tools or tactics, but because they’ve never been taught how to sell as themselves. Wes shares candid stories from his own journey as a founder and leader, and lays out a better path for MSPs who want more than temporary gains.

If you’ve ever felt uncomfortable in sales, struggled to connect with prospects, or just want to build a business that feels good and grows sustainably, this one’s for you.

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.

#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #EmailMarketing #EmailStrategy #MSPMarketing

Episode 19 - Cold Outreach That Actually Works (w/ Guest: James Milsom)

Mon, 21 Jul 2025 06:04:00 -0700

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 optional anymore
What subject lines actually earn opens
How to avoid spam folders and show up with value

Whether you’re sending outreach yourself or guiding your team, this episode will help you stop guessing and start improving.

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.

#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining #ColdOutreach #EmailMarketing #ColdEmail #ColdCalling

Episode 18 - Stop Killing Your Own Opportunities

Mon, 07 Jul 2025 06:00:00 -0700

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 momentum. And most MSP owners don’t even realize they’re doing it.

This episode isn’t about blame - it’s about awareness.
Once you can see the pattern, you can change it, and then everything can shift.

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.

#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #SalesTraining

Episode 17 - Stop Winging It, Start Winning (w/ Guest: Mike Fielstra)

Mon, 23 Jun 2025 06:00:00 -0700

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 every lead like a sure thing. If you've ever worn too many hats in your business, Mike’s journey will feel all too familiar.

This one’s a must-listen for anyone who's tired of fluff and ready for real talk about lead management, client follow-through, and creating a process that respects your time.

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.

#MSP #ManagedServiceProvider #ManagedServices #MSPSales #MSPMarketing #MSPCommunity #TechSales #ITServices #ManagedIT #CloudServices #ITConsulting

Episode 16 - The Only Way Out Is Through

Mon, 09 Jun 2025 06:47:41 -0700

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 means to keep showing up when things get hard.

If you’re tired, stuck, or wondering if you’ve got what it takes... this one is for you.
Because the only way out is through.

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.

#MSP #MSPSales #ManagedServices #TechSales #MSPCommunity #ITServices #ManagedIT #SalesTraining #ManagedServiceProvider

Episode 15 - From Tech Geek to Trusted Seller (w/ Guest: Nigel Moore)

Mon, 26 May 2025 06:00:00 -0700

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 leader. Nigel’s transformation from an introverted technician with sweaty palms to a trusted advisor who understands the true service behind selling is both inspiring and grounding.

If you’ve ever struggled with feeling “salesy,” or if your relationship with money gets in the way of making confident offers, this episode is for you.
Whether you know Nigel or not, this conversation brings something new to the table.

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.

Learn more about The Tech Tribe at https://TheTechTribe.com/

#MSPSales #ManagedServices #MSPMarketing #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #MSPServices #ITConsulting #MSPBusiness
#TheTechTribe #NigelMoore #SalesMindset #AuthenticSelling

Episode 14 - Rebuilding the Business You Actually Want to Run (w/ Guest: Michael Bakaic)

Mon, 12 May 2025 07:00:00 -0700

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 sits down with Brian Gillette and 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 is often a signal, not a failure
The difference between fixing your business vs. reimagining it
How simplifying his offer unlocked more freedom
Why storytelling closes sales

We also dig into the surprising evolution of Michael’s lead magnet - a cybersecurity audit tool that became his most effective conversation starter. You’ll hear how he repositioned a technical feature into a multi-stage trust-building funnel MSPs can actually use.

If you’re an MSP who’s hit a plateau, or is just tired of white-knuckling your way through growth, this episode is a powerful reminder that you can build something that works for your clients and feeds your soul too.

Learn more about Iceberg Cyber at https://www.icebergcyber.com/

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.

Learn more about Iceberg Cyber at https://www.icebergcyber.com

#MSPSales #ManagedServices #MSPMarketing #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #MSPServices #ITConsulting #MSPBusiness
#ITSupport #TechSupport #CyberSecurity

Episode 13 - The Truth About Leads and Growth (w/ Guest: Nate Freedman)

Mon, 28 Apr 2025 08:11:00 -0700

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 own sales process, how to create justified outreach that actually builds trust, and why responding faster could be your biggest competitive edge. Whether you're just starting out or scaling fast, this is a must-listen for any IT provider ready to level up their sales game.

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.

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#MSPSales #ManagedServices #MSPMarketing #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #MSPServices #ITConsulting #LeadGeneration

( Today's guest, Nate Freedman can be reached on LinkedIn or at www.techpromarketing.com )

Episode 12 - Authentic MSP Marketing in a Skeptical Market (w/ Guest: Katie Vreeland)

Thu, 10 Apr 2025 07:42:00 -0700

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. Whether you're an MSP owner doing your own outreach or you're leading a team, this episode will challenge you to think differently about visibility, awareness, and the customer journey.

Learn about building real trust without hype
Discover what actually resonates with today’s buyers
Reframe your marketing strategy to reflect your values and voice

Listen now and take your MSP marketing from forgettable to unforgettable.

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.

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#MSPSales #ManagedServices #MSPMarketing #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #MSPServices #ITConsulting

( Today's guest, Katie Vreeland can be reached on LinkedIn or at LuminaryCreative.co )

Episode 11 - SaaS vs. MSP Sales: What Works and What Doesn’t (w/ Guest: Tanner Cookson)

Thu, 27 Mar 2025 05:00:00 -0700

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 importance of relationship-driven selling to the challenges of longer sales cycles, we explore what it really takes to succeed in MSP sales.

If you’re an MSP looking to build the right sales team, don’t miss this conversation! We’ll help you understand what skills to prioritize, how to onboard sales reps effectively, and why a strong sales process is just as important as hiring the right person.

🔹 What’s the biggest challenge you’ve faced in hiring MSP sales reps? Let us know in the comments!

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.

(Today's guest, Tanner Cookson can be reached on LinkedIn. )
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#MSP #ManagedServices #ManagedServiceProvider #SalesStrategy #SalesTips #MSPSalesTraining #ITServices #MSPCommunity #ITConsulting #MSPMarketing #MSPSales #SalesHiring #SaaSSales #TechSales

Episode 10 - Fixing MSP Sales: A Forensic Approach (w/ Guest: Jeffrey Newton)

Thu, 13 Mar 2025 05:50:00 -0700

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 tech-focused MSPs often struggle with sales
How to blend process, psychology, and strategy for better conversion
The difference between just selling and truly solving problems

What’s the biggest sales roadblock you’ve faced? Let us know in the comments and watch this episode now.

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.

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#MSP #ManagedServices #ManagedServiceProvider #SalesStrategy #SalesTips #MSPSalesTraining #ITServices #MSPCommunity #ITConsulting #MSPMarketing
( Jeffrey Newton can be reached on LinkedIn. )

Episode 9 - Stop Being a Commodity (w/ Guest: Alex Farling)

Mon, 17 Feb 2025 04:59:00 -0800

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 MSP away from being “just another provider” and build some true differentiation.

What steps are you really taking to separate your MSP from the competition?
Listen in and start enacting some change starting today.

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.

.
#MSP #ManagedServices #ManagedServiceProvider #SalesStrategy #SalesTips #MSPSalesTraining #ITServices #MSPCommunity #ITConsulting #MSPMarketing
( Alex can be reached on LinkedIn as "Alex Farling" or through the Empath MSP website.)

Episode 8 - Why Marketing Should Start with Strategy (w/ Guest: Tim Fitzpatrick)

Thu, 30 Jan 2025 19:47:00 -0800

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 correctly aligned with your sales goals?
Could your messaging be clearer and more targeted?

This episode is packed with strategies to help you succeed!

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.

.
#MSP #ManagedServices #ManagedServiceProvider #SalesStrategy #SalesTips #MSPSalesTraining #ITServices #MSPCommunity #ITConsulting #MSPMarketing
( Tim can be reached on LinkedIn as "Tim P. Fitzpatrick" or through the RialtoMarketing.com website.)

Episode 7 - Keys to MSP Sales Team Success (w/ Guest: Casey Seaborn)

Wed, 15 Jan 2025 06:00:00 -0800

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 powerful sales approach. If you’re an MSP owner or sales leader, this episode will give you practical tips for taking your sales game to the next level. Learn to empower your team, refine your sales pitch, and attract the right clients.

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.

( MSPs who want more clarity in their finances, more actionable financial data, accounting, and tax advisory can speak to Casey directly at Stride Services. 440-251-7783 )

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#MSP #ManagedServices #ManagedServiceProvider #SalesStrategy #SalesTips #MSPSalesTraining #ITServices #MSPCommunity #ITConsulting

Episode 6 - Do It Right, Do It Well, Do It Over: Scale An MSP Sales Team (w/ Guest: John Davenjay)

Wed, 18 Dec 2024 17:56:00 -0800

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 struggling to make your first sales hire or wondering how to build an effective playbook for scaling your team, this episode offers real-world strategies to help you achieve efficient and lasting growth.

Take a listen and walk away with a few great ideas for expanding your own sales team.

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.
.
#MSP #ManagedServices #ManagedServiceProvider #SalesStrategy #SalesTips #MSPSalesTraining #Staffing #Scaling

Episode 5 - Transactional to Transformational Opportunities (w/ Guest: Kevin Clune)

Mon, 02 Dec 2024 06:12:00 -0800

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 recognize opportunities others overlook, position yourself as the go-to expert in your industry, and build a network of influence that pays dividends.

Tune in, and let's explore what it takes to be truly exceptional in MSP sales.

Episode 4 - Good, Great, or the Best?

Wed, 30 Oct 2024 17:49:40 -0700

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 does it mean to be the best. The journey to being the best isn’t for everyone. But if it’s your goal, you’ll learn how singular focus, self-discipline, and consistency can elevate your game.

This episode might challenge your thinking if you’ve ever questioned where you stand or how to reach that next level.

Tune in, and let's explore what it takes to be truly exceptional in MSP sales.

Episode 3 - Helpful vs. Hurtful: Crafting MSP Marketing Content (w/ Guest: Taher Hamid)

Tue, 01 Oct 2024 19:43:00 -0700

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.

Stay at the edge of change in the MSP sales world by subscribing to our brand-new Podcast now.

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.
.

#MSP #ManagedServices #ManagedServiceProvider #MSPSalesTraining #MSPSalesCoaching

Episode 2 - When MSP Sales Training Falls Short (w/ Guest: Robert Gillette)

Wed, 04 Sep 2024 01:40:00 -0700

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 technique - this episode examines how discipline and perseverance generate real-world results.

Stay at the edge of change in the MSP sales world by subscribing to our brand-new Podcast now.

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.
.

#MSP #ManagedServices #ManagedServiceProvider #MSPSalesTraining #MSPSalesCoaching

Episode 1 - Shifting the MSP Sales Mindset

Sun, 04 Aug 2024 23:12:16 -0700

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 can shift to a win-win-win approach that transforms the sales process.

Stay at the edge of change in the MSP sales world by subscribing to our brand new Podcast now.

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Turn your MSP growth efforts into a sales machine!
Learn more about the end-to-end sales training and development program from the experts at Feel-Good MSP.
.

#MSP #ManagedServices #ManagedServiceProvider #MSPSalesTraining #MSPSalesCoaching