

MSP Insider
MSP Insider
MSP Insider is your backstage pass to everything Managed Service Providers really care about. Forget the fluff—this is where we tackle the real challenges, share unfiltered advice, and dive into the stories that make the MSP world tick.From scaling your team to navigating the chaos of ticket management, we cut through the noise with insights that actually matter. Featuring industry leaders, battle-tested pros, and the occasional war story, every episode is packed with the strategies and tools you need to level up.If you’re ready to ditch the status quo and build an MSP business that works smarter—not harder—this is your podcast.
Episodes
Mentioned books

May 12, 2025 • 1h 12min
Unlocking Profit: How AI Transforms MSP Revenue in 2025
Is your MSP stuck in a pricing battle? Here’s the hard truth: if you’re still competing on price in 2025, you’re not scaling—you’re surviving. In this episode of MSP Insider, I sit down with Sagar Pandya to unpack the mindset shifts MSPs need to stay relevant and profitable. We go deep into how AI can give you an edge, why “consultative” isn’t just a buzzword, and what it takes to build client trust in a space moving faster than ever. If you’re tired of discounting your value—or trying to sell AI without really knowing how to use it—this one’s for you. 🎯 What You’ll Learn: • Why price-driven growth doesn’t scale • How to reposition yourself as a true advisor • Where AI fits (and doesn’t) in MSP operations • The real reason AI adoption is stalling • How to talk AI with clients—without overwhelming them • Practical strategies for sustainable MSP growth ⏱️ Timestamps: 0:00 – Intro 4:55 – Why competing on price is a trap 12:02 – Where AI actually helps MSPs grow 25:30 – Lessons from cloud → AI integration 37:14 – Real-world AI use cases for MSPs 49:38 – Building trust in a high-speed tech environment Powered by Cyft.ai – helping MSPs scale smarter

May 5, 2025 • 53min
The Future of MSP Platforms: AI, Integration & Growth | Chris Day
The MSP platform you’re using today? It might not get you where you want to go. In this episode of MSP Insider, I sat down with Chris Day to unpack what’s really broken in the MSP platform space—and where things are actually headed. We talk about: → Why “integration” is still mostly a buzzword → How AI is changing the way we manage data and deliver client value → What it really takes to create a platform that feels like it was built for you—not patched together for investors If you’ve ever felt like your tools don’t talk to each other—or that your stack is holding you back—this one’s worth your time. — Key Topics Covered: • Why traditional MSP platforms are falling behind • What true integration should look like • AI’s role in transforming client experience and operations • Building a scalable, context-aware customer journey • What to expect from MSP platforms by 2026 • What you can do today to close the gap ⏱️ Timestamps: 0:00 – Intro 1:20 – Chris Day on regrets and lessons learned 4:13 – Where MSP tools miss the mark 7:48 – Fixing broken integration 10:19 – Building a better client experience 14:03 – Behind the scenes at ScalePad 18:45 – AI, context, and the next big shift 26:37 – Why context wins 33:32 – Real steps to improve CX now

Apr 28, 2025 • 1h 7min
AI Compliance for MSPs: The Untapped Potentia
Is your MSP actually ready for the AI revolution? We unpack why ignoring AI could be the biggest risk to your business as we dive into the hard truths and strategies for leveraging AI and compliance in the MSP industry. Summary: In this episode, we dive deep into how MSPs can navigate the challenges of compliance and the transformative potential of AI. Learn how to transition your business strategy to stay competitive, overcome common misconceptions about AI, and simplify compliance by strategically implementing AI solutions. 🔍 Key Topics Covered: - Transformative AI strategies that increase MSP efficiency - The pressing role of compliance in MSP growth - Proven methods for integrating AI into MSP operations - Overcoming AI skepticism in the MSP community - Streamlining MSP processes with AI technologies - Preparing your MSP for 2025 and beyond - Utilizing AI to tackle cybersecurity challenges ⏱️ Timestamps: [00:00] Introduction to AI and Compliance in MSPs [07:30] The Compliance-Driven MSP Strategy [14:45] AI Misconceptions and How to Overcome Them [23:10] Practical AI Applications for MSP Efficiency [32:00] Planning for a Hybrid Workforce: AI and Humans [45:14] Future Trends and Recommendations for MSPs - This show is powered by Cyft.ai#MSPInsider #JeffreyNewton #Randy Blasik #VCISO #MSPGrowth

Apr 21, 2025 • 1h 5min
Why Most MSPs Fail at Compliance and How to Break the Cycle
Think compliance automation has you covered? You might be walking into a false sense of security. In this episode, I sat down with Tim Golden, founder of Compliance Scorecard, to unpack the real risks of relying too heavily on automation—and what it actually takes to build a scalable, secure compliance program as an MSP. This one’s for MSP leaders who want to grow and protect what they’ve built. What we cover: • Why automation alone isn’t enough to keep you (or your clients) safe • What a real compliance foundation looks like • Turning compliance into momentum—not just maintenance • What the FTC safeguards really mean for your MSP • How to create a compliance-first culture that scales • Real examples of what’s working in the field Timestamps: 00:00 – Intro 05:00 – The compliance myths holding MSPs back 12:00 – What strong compliance actually looks like 22:00 – FTC safeguards: what you need to know 30:00 – From “check the box” to continuous monitoring 40:00 – Building a culture that gets it 55:00 – Final takeaways Powered by Cyft.ai #MSPInsider #JeffreyNewton #TimGolden #VCISO #MSPGrowth

Apr 14, 2025 • 59min
The VCISO Approach That Transforms MSP Profitability with Jesse Miller
In episode 15 of MSP Insider, host Jeffrey Newton sits down with Jesse Miller, founder of Power PSA Consulting, for a no-BS conversation about why most MSPs fail at cybersecurity sales. Through candid discussion, Jesse reveals why obsessing over security tech stacks instead of business risk is killing your margins, how his own first security program "bled cash" until he changed his approach, and why "comfort zone thinking" is the true barrier to MSP growth. Key Topics Covered: • Why technical cybersecurity stacks alone are impossible to sell profitably • How to transition from technical expert to strategic risk advisor • The critical difference between vCIO and vCISO conversations with clients • Why "professional perfection" mentality kills MSP cybersecurity programs • How to structure security offerings that clients actually understand and buy Timestamps: 0:00 - Introduction to cybersecurity challenges for MSPs 4:03 - Jesse's journey from technical expert to strategic advisor 10:17 - Why most MSPs get stuck in their comfort zones 16:35 - The critical difference between vCIO and vCISO services 22:06 - Why "professional perfection" kills cybersecurity programs 31:22 - Building flexible frameworks vs. rigid security packages Whether you're struggling to make cybersecurity profitable or looking to expand your existing security practice, this episode delivers practical advice about what it really takes to sell and deliver security services that clients actually value and pay for. This show is powered by cyft.ai #MSPInsider #JeffreyNewton #JesseMiller #VCISO #CybersecurityServices #MSPGrowth #RiskManagement

Apr 7, 2025 • 54min
Stop Chasing 'Silver Bullet' Tech and Fix Your People Problem” with Damien Stevens
In episode 14 of MSP Insider, host Jeffrey Newton sits down with Damian Stevens, host of MSP Mindset and founder of Scarcity, for a raw conversation about why most MSPs are getting hiring completely wrong. Through brutally honest discussion, Damian reveals why four-year degree requirements are killing your talent pipeline, how to spot "high trajectory" candidates that conventional hiring processes miss, and why obsessing over technical skill sets often leads to culture disasters that cost you far more in the long run. Key Topics Covered: • Why conventional hiring processes filter out the most innovative potential employees • How to identify "unconventional hires" with higher growth trajectories than traditional candidates • The critical shift from "time-to-hire" thinking to "time-to-performance" measurement • Why culture problems are usually the real constraint in MSP growth (not tech or leads) • How to build a hiring process that reflects your actual culture, not generic corporate templates Timestamps: 0:00 - Introduction to MSP hiring challenges 4:12 - Why conventional job descriptions are killing your talent pipeline 8:35 - Identifying "high trajectory" unconventional hires 14:27 - The shift from "time-to-hire" to "time-to-performance" thinking 22:06 - Culture as the hidden constraint in MSP growth 28:43 - Building a hiring process that shows your true culture Whether you're struggling with finding good technical talent or constantly dealing with culture mismatches after hiring, this episode delivers uncomfortable truths about what it really takes to build an MSP team that drives sustainable growth in 2025 and beyond. This show is powered by cyft.ai #MSPInsider #JeffreyNewton #DamianStevens #MSPHiring #TalentAcquisition #MSPCulture #UnconventionalHiring

Mar 31, 2025 • 54min
Stop Losing Prospects Mid-Pitch: Sales Recovery Tactics with Jonathan Schofield
In episode 13 of MSP Insider, host Jeffrey Newton sits down with Jonathan Schofield, a no-nonsense sales pro in the IT services space, who tells it like it is about those painful moments when your prospect's eyes glaze over. Jonathan cuts through the BS about why your monologuing is killing deals, how to spot the exact moment you've lost someone, and his battle-tested techniques to snap prospects back to attention. Key Topics Covered: • The telltale signs your prospect has mentally left the building mid-pitch • Jonathan's "pattern interrupt" technique that forces re-engagement (even if they don't want to) • The mutual expectations framework that prevents tune-out in the first place • Why most MSPs waste thousands on marketing "silver bullets" that never hit the target • How to get brutally honest about who your ideal customer actually is (hint: it's not "SMEs with 20+ employees") Timestamps: 0:00 - Introduction to sales engagement disasters we've all experienced 3:57 - The exact moment you realize you've lost your prospect's attention 8:18 - The pattern interrupt technique that works every time 14:53 - Why "accidental entrepreneurs" struggle with sales ownership 22:31 - Getting real about your ideal customer profile 31:05 - "Where thy prospect is, there thou shalt also be" If you're tired of watching opportunities slip away as prospects check email during your pitch, this episode delivers the uncomfortable truths about what it really takes to keep decision-makers locked in during sales conversations in 2025 and beyond. This show is powered by cyft.ai #MSPInsider #JeffreyNewton #JonathanSchofield #SalesEngagement #MSPGrowth #SalesStrategy #ITServices

Mar 24, 2025 • 52min
Why Your MSP Sales Training Is Garbage (And What Really Works) - Robert Gillette
In this episode of MSP Insider, host Jeffrey Newton sits down with Robert Gillette, founder of MSP Dojo, for a candid conversation about why most MSP sales programs fail and what actually drives results. Through honest discussion, Robert reveals why making hundreds of cold calls isn't enough, how lack of confidence impacts sales meetings "like body odor," and the psychological barriers preventing MSP owners from achieving sales success. Key Topics Covered: • The three critical levers of MSP sales success beyond activity volume • Why most MSP owners sabotage their sales hires from day one • How compensation plans can either motivate or destroy sales momentum • The psychological "pucker effect" that kills rainmaker relationships • Why sales is a journey of self-development, not just tactics Timestamps: 0:00 - Introduction to MSP sales challenges 7:22 - The three critical levers of sales success 12:05 - Why hiring a sales rep usually backfires 18:33 - The psychology of successful sales 22:19 - Building effective compensation plans 27:46 - Protecting your rainmakers Whether you're struggling with making your first sales hire or looking to improve your existing sales process, this episode delivers uncomfortable truths about what it really takes to grow an MSP through effective sales in 2025 and beyond. This show is powered by cyft.ai #MSPsales #JeffreyNewton #RobertGillette #salestraining #ITchannel #MSPgrowth #salesstrategy #managedservices

Mar 17, 2025 • 45min
Fix Your Service Leaks Before Turning On The Sales Faucet - Keith Marchiano
In this episode of MSP Insider, host Jeffrey Newton sits down with Keith Marciano, Senior Executive Coach at Pax8 Academy, for a practical conversation about the operational foundations MSPs need before focusing on sales growth. Through candid discussion, Keith reveals why generating more leads without fixing service delivery creates bigger problems, how to approach modern buyers who've already done their research, and the specific metrics that indicate MSP health.Key Topics Covered:• Why your service foundations must be solid before ramping up marketing• The "Results Selling Framework" that focuses on client business outcomes• How to identify if unprofitable clients are "your problem" or "their problem"• The benchmark metrics every MSP should be tracking (50-60% margins, 6.5 billable hours)• Why specializing in 1-3 industries creates more value than being a generalistTimestamps:0:00 - Introduction to MSP operational challenges4:09 - Understanding the modern buyer journey10:22 - Strategic ways to engage decision-makers16:30 - The Results Selling Framework27:03 - Critical operational metrics to track33:21 - Addressing unprofitable legacy clientsWhether you're struggling with service delivery efficiency or trying to increase your managed services margins, this episode delivers practical advice about what it really takes to build a profitable MSP in 2025 and beyond.This show is powered by cyft.ai#MSPInsider #JeffreyNewton #KeithMarciano #MSPGrowth #ManagedServices #Pax8Academy #ITBusinessStrategy

Mar 10, 2025 • 59min
The Painful Truth About Why Most MSPs Can't Sell - Brian Gillette
In Episode 10 of MSP Insider, host Jeffrey Newton sits down with Brian Gillette, founder of Feel Good MSP and host of the MSP Sales Podcast, for a raw conversation about why most MSPs struggle with sales and the uncomfortable truths about what it takes to grow. Through candid discussion, Brian reveals why technology often creates distance between MSPs and their clients, and how to rebuild the human connection that drives real growth.Key Topics Covered:• Why most technical founders struggle with sales psychology• How to overcome the "victim mindset" in MSP sales• Why adding more technology often hurts client relationships• The critical importance of human connection in managed services• Practical steps for facing sales fears and taking actionTimestamps:0:00 - Introduction7:46 - The Victim Mindset in MSPs15:29 - Overcoming Sales Fear32:11 - The Human Side of Service42:07 - Technology vs Connection54:26 - Key TakeawaysWhether you're struggling with sales or looking to rebuild genuine client relationships, this episode delivers uncomfortable truths about what it really takes to grow an MSP in 2025 and beyond.This show is powered by cyft.ai


