MSP Mastery: Ctrl-Alt-Deliver

Jeni Clift, Nick Clift
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Welcome to Ctrl-Alt-Deliver: MSP Mastery — the podcast for IT leaders, MSP owners, and service delivery professionals who want to elevate performance, improve processes, and stay ahead in the fast-changing managed services landscape.

  1. 2D AGO

    The Insurance Trap: Is Your MSP Unknowingly Underwriting Your Clients? with Tim Stephinson

    Welcome to MSP Mastery, the podcast for MSP owners and leaders who want to build a better MSP; one that actually works for them. I’m Jeni Clift, joined by my husband and long-time business partner, Nick Clift. Together, we’ve spent decades building, scaling, and eventually exiting our own MSP business. Over the years, we’ve seen firsthand that the MSPs who thrive are the ones willing to evolve. And right now, few shifts are more important than how we manage risk, professional liability, and the critical boundaries between our business and our clients’ data. In this episode, we sit down with Tim Stephinson, COO at Sherpa Tech and an Australian insurance specialist with over 20 years of commercial experience. Tim helps us cut through the complexity and confusion surrounding cyber insurance and professional indemnity to ensure MSP owners are properly protected without the usual friction. Here’s what we covered together:  ✅ Why the phrase "we don't need insurance because our MSP has it" is a massive red flag  ✅ The "survival vs. inconvenience" rule: how to prioritise the risks that could actually kill your business  ✅ Why you must have the insurance conversation before onboarding a high-risk client  ✅ The vital difference between a "process failure" and an "absence of process" (and which one is insurable)  ✅ How to stop being the silent insurer for your clients and start saying "your data, your problem" We created this podcast to share the real conversations and lessons we wish we’d had more of while running our own MSP; practical insights from people who understand the challenges, pressures, and opportunities in this industry. Whether you are questioning your current coverage, struggling to explain cyber responsibility to your clients, or worried about being "on the hook" for a third-party breach, this episode with Tim offers a grounded and timely perspective on what leaders need to do now to build a business that is both profitable and fulfilling. 👉 Connect with Tim on LinkedIn: Tim Stephinson 🌐 Learn more about Sherpa Tech: sherpatech.com.au  🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog

    47 min

  2. APR 6

    Fish in a Sandpit: Finding the Right People and Processes for Scalable Growth with Melissa Hockenberry

    Welcome to MSP Mastery, the podcast for MSP owners and leaders who want to build a better MSP; one that actually works for them. I’m Jeni Clift, joined by my husband and long-time business partner, Nick Clift. Together, we’ve spent decades building, scaling, and eventually exiting our own MSP business. Over the years, we’ve seen firsthand that the MSPs who thrive are the ones willing to evolve. And right now, few shifts are more important than how we lead our people and the intentional decisions we make around operational discipline. In this episode, we sit down with Melissa Hockenberry, an MSP industry veteran with over 20 years of experience, to unpack what it really takes to transition from a reactive "firefighting" culture to a proactive, system-driven business. Melissa shares her unique perspective on client retention and why understanding the "friction" in your team is the only true path to a scalable MSP. Here’s what we covered together:  ✅ Why "knee-jerk" reactions to problems are masking deeper systemic issues  ✅ The "Fish in a Sandpit" analogy and why letting the wrong fit go is a gift  ✅ Why standardisation is more important than ever in an era of rapid AI and M&A shifts  ✅ How to identify if you have a "people problem" or actually a "process problem"  ✅ Simple steps to experience your own business from the client’s perspective to find hidden friction We created this podcast to share the real conversations and lessons we wish we’d had more of while running our own MSP; practical insights from people who understand the challenges, pressures, and opportunities in this industry. Whether you are struggling with team performance, looking to improve client retention, or questioning why your current processes aren't scaling, this episode with Melissa offers a grounded and timely perspective on what leaders need to do now to build a business that is both profitable and fulfilling. 👉 Connect with Melissa on LinkedIn: Melissa Hockenberry 🌐 Learn more about From the Front to the AC: ftftac.com 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog

    50 min

  3. MAR 29

    Building an MSP that Runs without You with Allan Michelmore

    Welcome to MSP Mastery, the podcast for MSP owners and leaders who want to build a better MSP; one that actually works for them. I’m Jeni Clift, joined by my husband and long-time business partner, Nick Clift. Together, we’ve spent decades building, scaling, and eventually exiting our own MSP business. Over the years, we’ve seen firsthand that the MSPs who thrive are the ones willing to evolve. And right now, few shifts are more important than the way we structure our teams and leverage modern tools like AI. In this episode, we sit down with Allan Michelmore, Managing Director of Control Networks, to unpack what it really takes to build a business that is an entity in itself. Allan shares his deep experience with offshore resourcing and why systems and documentation are the only true path to freedom for an MSP owner. Here’s what we covered together:  ✅ Why the 80 20 rule is the secret to overcoming documentation overwhelm  ✅ How to put essential guardrails around AI to protect your business and your clients  ✅ The biggest myths about offshoring and why it fails for most MSPs  ✅ Why treating your offshore team as true colleagues is non negotiable for success  ✅ How to transition from being the bottleneck to having a business that runs with or without you We created this podcast to share the real conversations and lessons we wish we’d had more of while running our own MSP; practical insights from people who understand the challenges, pressures, and opportunities in this industry. Whether you’re already using offshore resources, starting to think about AI governance, or questioning how to finally step out of the day to day operations, this episode with Allan offers a grounded and timely perspective on what leaders need to do now to stay ahead. 👉 Connect with Allan on LinkedIn: Allan Michelmore 🌐 Learn more about Control Networks: Control Networks 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog

    47 min

  4. MAR 22

    Tas Gray: Why AI and Automation Will Make or Break the Modern MSP

    Welcome to MSP Mastery, the podcast for MSP owners and leaders who want to build a better MSP; one that actually works for them. I’m Jeni Clift, joined by my husband and long-time business partner, Nick. Together, we’ve spent decades building, scaling, and eventually exiting our own MSP business. Over the years, we’ve seen firsthand that the MSPs who thrive are the ones willing to evolve. And right now, few shifts are more important than the rise of AI and automation. In this episode, we sit down with Tas Gray, Managing Director of Axiom IT, to unpack what AI and automation really mean for MSPs — not as hype, but as a practical business reality. Tas shares why increasing efficiency, reducing manual effort, and driving costs down are no longer optional for businesses that want to stay competitive and profitable. Here’s what we covered together:  ✅ Why AI and automation can dramatically improve efficiency and reduce operating costs  ✅ How manual processes can leave MSPs vulnerable to shrinking margins and rising costs  ✅ Why clients are already looking for meaningful ways to use AI to improve productivity  ✅ The risks MSPs face if they delay automation for too long  ✅ How AI is reshaping expectations across software, service delivery, and business operations We created this podcast to share the real conversations and lessons we wish we’d had more of while running our own MSP — practical insights from people who understand the challenges, pressures, and opportunities in this industry. Whether you’re already experimenting with AI, starting to think more seriously about automation, or questioning how these changes will affect your MSP in the years ahead, this episode with Tas offers a grounded and timely perspective on what leaders need to do now to stay ahead. 👉 Connect with Tas on LinkedIn: Tas Gray 🌐 Learn more about Axiom IT: Axiom IT 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog

    54 min

  5. MAR 15

    Why Most MSP Marketing Leaks with Niall Mackay

    Welcome to MSP Mastery Podcast. I’m Jeni Clift, joined by my husband and business partner Nick Clift. Together, we spent nearly 30 years building, scaling, and eventually exiting our own MSP business. Along the way, we learned something fundamental. Operational maturity isn't just about your tech stack—it’s about how you present your authority to the market. In this episode, we’re joined by Niall Mackay, the "Podcast Guy" and founder of Seven Million Bikes Podcasts. Niall lives and breathes audio and video production, helping founders move past the "shiny tool" phase to create content that actually sticks. As the editor behind the scenes of Control Alt Deliver for the last six months, Niall has developed a unique outsider-in perspective on the MSP industry. He’s seen firsthand how the principles of delegation, automation, and niche authority apply just as much to a podcast as they do to a managed service provider. What becomes clear in this conversation is that most MSP marketing doesn’t explode. It leaks. We explore: The Exit Strategy Reality Check: Why building a business around yourself is just selling a client list, not a saleable asset.The DIY Trap: Why spending 8 hours editing a podcast is a "false economy" when your time is worth hundreds per hour.Removing the Founder: How Niall used Notion and AI to automate his production and take himself out of the day-to-day grind.The ROI of Authority: Why your podcast should be a lead magnet that sends people back to your business, not your guests'.Consistency vs. Frequency: Why a weekly cadence is the non-negotiable standard for building trust.The "Cost" of Waiting: Why every business will eventually have a podcast and why the window to stand out is closing.Video & 4K Standards: The minimum viable tech you need to stop looking "grainy" and start looking professional.We also discuss the psychological hurdle of "hating your own voice" and Niall’s pointed reminder: “Don't give free advertising to your guests. They're there to help prop you up. You need to be the expert.” This episode is not about shiny microphones. It’s about operational discipline. Brand authority. Founder freedom. If you are an MSP owner who has been "thinking about" starting a podcast but is worried about the time drain, this conversation provides the roadmap to doing it right. Connect with Niall Mackay on LinkedIn: https://www.linkedin.com/in/niallmackay/ Learn more about Seven Million Bikes Podcasts: https://www.sevenmillionbikes.com/ Listen to this episode and explore more MSP Mastery conversations at: https://www.mspmastery.blog/episodes Join our Facebook community for MSP owners and leaders: https://www.facebook.com/groups/192546407744556 Subscribe to our YouTube channel: https://www.youtube.com/@MSPMastery Follow MSP Mastery on Instagram: https://instagram.com/mspmastery

    49 min

  6. MAR 1

    Adam Ross: The Hidden Margin Leak Inside Your MSP

    Welcome to Ctrl Alt Deliver: MSP Mastery Podcast. I’m Jeni Clift, joined by my husband and business partner Nick Clift. Together, we spent nearly 30 years building, scaling, and eventually exiting our own MSP business. Along the way, we learned something fundamental. Recurring revenue only works when it’s managed properly. In this episode, we’re joined by Adam Ross, Co-Founder of CloudOlive and a long-time leader in the MSP ecosystem, with senior roles spanning Autotask, Datto, and now the venture-backed startup world. Adam has spent more than 15 years working alongside MSPs across Australia, Europe, and globally. Today, through CloudOlive, he has visibility into the billing, licensing, and recurring revenue structures of hundreds of MSPs — and what he sees is both simple and confronting. What becomes clear in this conversation is that most margin problems don’t explode. They leak. We explore: Why missing a single license for one month can wipe out six months of marginHow “homemade” PSA service codes quietly erode profitabilityWhy bundling services may simplify invoices but destroys cost visibilityThe hidden risks inside recurring billing processesWhere automation helps — and where blind automation makes things worseWhy vendor consolidation and disciplined naming conventions matter more than new toolsThe uncomfortable truth about founder-led growth and client engagementWe also discuss retention discipline, operational maturity, and Nick’s pointed reminder: “If you are not calling existing customers, you're not calling new customers. Somebody else is calling your customers.” This episode is not about shiny tools. It’s about operational clarity. Margin integrity. Leadership discipline. If you are an MSP owner who assumes your recurring revenue is “under control,” this conversation may challenge that assumption — in a constructive way. Connect with Adam Ross on LinkedIn: https://www.linkedin.com/in/madassor/ Learn more about CloudOlive: https://www.cloudolive.com/ Listen to this episode and explore more Ctrl Alt Deliver conversations at: https://www.mspmastery.blog/episodes Join our Facebook community for MSP owners and leaders: https://www.facebook.com/groups/192546407744556 Follow MSP Mastery on Instagram: https://instagram.com/mspmastery

    49 min

  7. FEB 22

    Aaron Smith: There’s Money in the Backyard

    Welcome to Ctrl Alt Deliver: MSP Mastery Podcast. I’m Jeni Clift, joined by my husband and business partner Nick Clift. Together, we spent nearly 30 years building, scaling, and eventually exiting our own MSP business. Along the way, we learned something fundamental. Growth alone doesn’t build a strong MSP. Structure does. In this episode, we’re joined by Aaron Smith, Founder of Morphability and a specialist in helping MSPs build scalable, repeatable sales systems that don’t rely on founder heroics. Aaron has spent years inside MSPs leading sales functions, driving growth, and learning firsthand what happens when ambition outpaces structure. Today, he works with MSP owners to move beyond personality-driven sales and build disciplined, sustainable growth engines. What becomes clear in this conversation is that rapid growth isn’t always success. Sometimes it’s the beginning of instability. We explore: Why measured, controlled growth is infinitely better than scaling too fastHow hiring before structure can quietly destabilise your businessWhy there is always “money in the backyard” inside every MSPThe risk of staying in owner-led sales for too longWhy structure beats personality-driven salesThe difference between hunter roles and compliance-focused account managementWe also talk candidly about owner bottlenecks, executive-level client relationships, and the uncomfortable truth that many MSPs stall not because of market conditions — but because of leadership ceilings. This episode is not about chasing more revenue. It’s about building a business that can handle the revenue you chase. If you are an MSP owner thinking about growth, hiring a BDM, or wondering why your business feels stuck at the same revenue ceiling, this conversation will challenge and clarify your next move. Connect with Aaron Smith on LinkedIn: https://www.linkedin.com/in/morphabilityas/ Learn more about Morphability: https://www.morphability.au/ Listen to this episode and explore more Ctrl Alt Deliver conversations at https://www.mspmastery.blog/episodes Join our Facebook community for MSP owners and leaders: https://www.facebook.com/groups/192546407744556 Follow MSP Mastery on Instagram: https://instagram.com/mspmastery

    43 min

  8. FEB 15

    Jane Save: Why Avoiding One Person Can Destroy Your Entire Team in MSP Businesses

    Welcome to Ctrl Alt Deliver: MSP Mastery Podcast. I’m Jeni Clift, joined by my husband and business partner Nick Clift. Together, we spent nearly 30 years building, scaling, and eventually exiting our own MSP business. Along the way, we learned something fundamental. Great service delivery isn’t just about systems and processes. It’s about people, performance, and the courage to lead when conversations get uncomfortable. In this episode, we’re joined by Jane Save, Director of The Save Group, a straight-talking HR partner to SMEs and a trusted advisor to many MSPs navigating growth, retention, and performance challenges. Jane has spent more than 20 years helping business owners manage people without the corporate jargon or unnecessary drama. Her approach is practical, human, and grounded in protecting both the business and the team. What becomes clear in this conversation is that most culture problems don’t explode overnight. They erode quietly. We explore: Why avoiding one disengaged employee can slowly damage your entire teamHow psychological safety allows employees to speak up early instead of quietly quittingWhy performance management should be timely, objective, and clear — not saved for annual reviewsThe power of “stay interviews” in preventing unexpected resignations  And https://www.thesavegroup.com.auwhy difficult conversations are often easier than leaders imagineWe also talk candidly about leadership hesitation, knowledge risk in MSP environments, and the relief teams feel when standards are upheld. This episode is not about HR theory. It’s about practical leadership. If you are an MSP owner or leader who knows something in your team feels “off” but hasn’t acted yet, this conversation will give you clarity and confidence. Connect with Jane Save on LinkedIn: https://www.linkedin.com/in/janesave Learn more about The Save Group: https://www.thesavegroup.com.au Listen to this episode and explore more Ctrl Alt Deliver conversations at https://www.mspmastery.blog/episodes Join our Facebook community for MSP owners and leaders: https://www.facebook.com/groups/192546407744556 Follow MSP Mastery on Instagram: https://instagram.com/mspmastery

    46 min
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About

Welcome to Ctrl-Alt-Deliver: MSP Mastery — the podcast for IT leaders, MSP owners, and service delivery professionals who want to elevate performance, improve processes, and stay ahead in the fast-changing managed services landscape.

Information

  • Creator
    Jeni Clift, Nick Clift
  • Years Active
    2025 - 2026
  • Episodes
    35
  • Rating
    Explicit
  • Copyright
    © 2026 MSP Mastery: Ctrl-Alt-Deliver
  • Show Website
    MSP Mastery: Ctrl-Alt-Deliver