MSP Mastery: Ctrl-Alt-Deliver

PODCAST · business

MSP Mastery: Ctrl-Alt-Deliver

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. 38

    The Traineeship Strategy: Building a Team That Stays and Grows with Nathan Gemmill

    Welcome to MSP Mastery: Ctrl-Alt-Deliver Podcast, 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.In this episode, we sit down with Nathan Gemmill, someone we have known since he joined us straight out of high school as a trainee. Over the years, we watched Nathan grow from a junior team member into a confident and capable IT professional, making this a deeply personal and insightful conversation about career development in the MSP industry.Nathan shares his journey from school leaver to experienced technician, reflecting on the value of learning on the job, the importance of having the right support around you, and why curiosity can be one of the greatest assets in a technology career. We also explore the realities of bringing trainees into an MSP, how to help them succeed, and why creating a culture where people can make mistakes and learn from them is essential for long term success.Here is what we covered together:✅ How Nathan’s IT career began with one unexpected conversation at a service station✅ Why traineeships can be a powerful long term strategy for MSPs✅ The importance of buddy mentors, structure, and support in the early days✅ Why curiosity, hands on learning, and real world experience matter so much in IT✅ How to build a workplace culture where mistakes are owned, communicated, and resolved✅ The differences between MSP life and internal IT roles✅ Why training the trainer can help build stronger teams and future leadersWe 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.👉 Connect with Nathan Gemmill on LinkedIn: Nathan Gemmill 👉 Learn more about GMHBA: GMHBA 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog 📸 Follow on Instagram: instagram.com/mspmastery ▶️ Subscribe on YouTube: youtube.com/@MSPMastery

  2. 37

    The Growth Trap with Brendan Rose: Why Hiring and Hoping is Costing Your 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 Clift. Together, we’ve spent decades building, scaling, and eventually exiting our own MSP business.In this episode, we sit down with Brendan Rose, a true veteran of the Adelaide MSP scene and business consultant at Morphability. Brendan brings over 20 years of experience across sales, operations, and executive leadership, offering a unique perspective on what it actually takes to scale a team without burning through cash.Brendan shares the hard truths about the growth paradox, why simply hiring a BDM to sell more often fails, and why building the map before you hire the person is the only way to set them up to succeed. We also dive into the idea of breaking up marriages, and why your next high value client is likely sitting in your competitor’s portfolio right now.Here is what we covered together:✅ Why hiring a salesperson without a plan is the fastest way to waste money✅ The breaking up marriages model and how to disrupt the bond between your competitor and your future client✅ Why your next customer is not sitting at MSP industry events and where you should be showing up instead✅ The lead generation trap and why you need to fix your internal sales engine before chasing volume✅ The first sales hire and why the owner must stay close for longer than they think✅ Sales versus operations and how to align delivery capacity so growth does not break your businessWe 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.👉 Connect with Brendan on LinkedIn: Brendan Rose 👉 Learn more about Morphability: morphability.au 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog 📸 Follow on Instagram: instagram.com/mspmastery ▶️ Subscribe on YouTube: youtube.com/@mspmastery

  3. 36

    The Second Deal Trap and the Six Month Slump with Ryan Fuzzy Spillane

    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.In this episode, we sit down with Ryan Fuzzy Spillane, CEO of 360 Consulting and a long time MSP operator turned trusted adviser. Ryan has been on both sides of the table, completing multiple acquisitions and then living through the integration journey after a major exit.Ryan shares the hard truths MSP owners need to hear about acquisitions, valuation, and what really happens after the deal is signed, including the moment many owners do not expect: the six month mark can be the lowest point when you still carry responsibility but no longer have control.Here’s what we covered together:✅ Why your second acquisition is often your most dangerous✅ Why product revenue adds little to business value, and why recurring revenue changes the valuation conversation✅ Why you cannot acquire when your leadership team is already at full capacity✅ What sellers need to tighten up before an exit, including agreements, financial clarity, and documentation✅ The post sale reality and how to prepare for what comes nextWe 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.👉 Connect with Ryan on LinkedIn: Ryan Fuzzy Spillane 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog 📸 Follow on Instagram: instagram.com/mspmastery ▶️ Subscribe on YouTube: youtube.com/@mspmastery

  4. 35

    The "Enthusiastic Intern" and the Impact Effort Matrix for AI Adoption with Andrew Herbert

    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 rise of AI and automation.In this episode, we sit down with Andrew Herbert, founder of Remap AI, to pull back the curtain on how MSPs can actually implement AI without getting lost in the noise. Andrew shares his "operator first" approach, explaining why treating AI as an "enthusiastic intern" is the best way to maintain quality while scaling output.Here’s what we covered together:✅ Why thinking of AI as an enthusiastic intern helps you manage its knowledge and its limitations✅ How to use the Impact Effort Matrix to identify the high value friction points in your business✅ The "Annualised Sunk Cost of Time" and how it creates a financial business case for automation✅ Why MSPs must avoid free AI accounts and the critical security risks of "leaving the keys on the table"✅ How to transition from being a tech focused MSP to an "AI ready" business partner for your clientsWe 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 looking for quick wins in your operations or a long term strategy to lead your clients through the AI revolution, this episode with Andrew offers a grounded and practical roadmap for what is possible today.👉 Connect with Andrew on LinkedIn: Andrew Herbert 🌐 Learn more about Remap AI: Remap AI 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog

  5. 34

    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

  6. 33

    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 frictionWe 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

  7. 32

    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 youWe 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

  8. 31

    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 operationsWe 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

  9. 30

    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/episodesJoin our Facebook community for MSP owners and leaders:https://www.facebook.com/groups/192546407744556Subscribe to our YouTube channel:https://www.youtube.com/@MSPMasteryFollow MSP Mastery on Instagram:https://instagram.com/mspmastery

  10. 29

    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/episodesJoin our Facebook community for MSP owners and leaders: https://www.facebook.com/groups/192546407744556Follow MSP Mastery on Instagram: https://instagram.com/mspmastery

  11. 28

    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/episodesJoin our Facebook community for MSP owners and leaders:https://www.facebook.com/groups/192546407744556Follow MSP Mastery on Instagram:https://instagram.com/mspmastery

  12. 27

    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/janesaveLearn more about The Save Group:https://www.thesavegroup.com.auListen to this episode and explore more Ctrl Alt Deliver conversations athttps://www.mspmastery.blog/episodesJoin our Facebook community for MSP owners and leaders:https://www.facebook.com/groups/192546407744556Follow MSP Mastery on Instagram:https://instagram.com/mspmastery

  13. 26

    The Lessons 2025 Made Impossible to Ignore

    Welcome to Ctrl Alt Deliver: MSP Service Delivery Mastery. 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 defined by tools, frameworks, or certifications.It’s defined by leadership, clarity, and the discipline to run a business that can stand on its own.This episode is a little different.Instead of a guest interview, Nick and I step back and reflect on several key conversations from 2025, revisiting episodes 9–12 and unpacking the patterns we continue to see across MSPs at every stage of growth.What becomes clear is that most service delivery challenges aren’t technical.They’re operational, cultural, and leadership-driven.In this deep dive, we explore:Why even the most experienced engineers still need context around your business, your clients, and your implementationHow MSPs often over-engineer tools and reporting while under-engineering simplicity and clarityWhy most strong MSP–client relationships aren’t actually governed by SLAs, but by trust and shared expectationsThe discipline of running your business as if you were preparing it for exit — even if you never plan to sellAnd how culture and leadership show up when pressure hitsWe also talk candidly about what happens after an MSP exit, the identity shift many owners don’t anticipate, and why having a clear “what’s next” matters just as much as building the business itself.This is not a recap for the sake of looking back.It’s about connecting the dots, recognising patterns early, and making intentional decisions that lead to calmer, more resilient service delivery.If you are an MSP owner, leader, or service delivery professional looking to move beyond reactive operations and toward true MSP mastery, this episode will resonate.Listen to this episode and explore more Ctrl Alt Deliver conversations athttps://www.mspmastery.blog/episodesJoin our Facebook community for MSP owners and leaders:https://www.facebook.com/groups/192546407744556Follow MSP Mastery on Instagram:https://instagram.com/mspmastery

  14. 25

    Punk Leadership in Cybersecurity with Mitchell Colton

    Welcome to Ctrl Alt Deliver: MSP Service Delivery Mastery.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 critical.Great service delivery isn’t defined by tools, frameworks, or certifications.It’s defined by how you lead when things go wrong.In this episode, we’re joined by Mitchell Colton, Managing Director of Colton Computer Technologies, and a highly respected MSP leader who has lived through one of the most challenging situations an MSP can face.Mitchell shares a candid, firsthand account of navigating a major third-party data breach that impacted one hundred and thirty eight client organisations. The breach wasn’t caused by his business, but the responsibility, pressure, and consequences landed squarely with him and his team.What stands out in this conversation is not the technical response, it’s the human one.We talk about the emotional weight of leading through uncertainty, the reality that incidents become long marathons rather than short sprints, and why calm, structured leadership matters more than speed. Mitchell explains how clear roles, simple checklists, and early, consistent communication helped steady both clients and staff during months of ongoing investigation and regulatory oversight.Mitchell also shares hard-earned lessons about cyber insurance, incident response readiness, and the importance of building trusted relationships with brokers, lawyers, and advisors before you need them. He challenges MSPs to rethink how prepared they really are for incidents that are out of their control — and the hidden business impact that follows long after the headlines fade.Throughout the episode, we explore the often-unspoken reality of MSP leadership.The responsibility of holding sensitive data.The reputational risk carried on behalf of clients.And the quiet toll incidents take on founders, leaders, and teams.This is an honest and deeply practical conversation about leadership under pressure, trust built through clarity, and what it really means to show up for clients and people when the stakes are highest.If you are an MSP owner, leader, or service delivery professional responsible for client trust, risk management, and team wellbeing, this episode is essential listening.Listen to this episode and explore more Ctrl Alt Deliver conversations at https://www.ctrl-alt-deliver.blog/episodesExplore more about Mitchell Colton and Colton Computer Technologies https://coltoncomputers.com.au/

  15. 24

    Vivienne Winborne on Transparency, Resilience, and Client Trust in Crisis

    Welcome to Ctrl Alt Deliver: MSP Service Delivery Mastery.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.Over that time, we learned something fundamental. Great service delivery is not proven when everything is running smoothly. It is proven when things go wrong.In this episode, we’re joined by Vivienne Winborne, Senior Marketing Manager at One Little Seed and a long time specialist in MSP and IT channel marketing.Vivienne has spent more than 16 years working across agencies, startups, and the MSP ecosystem, supporting service providers, vendors, and distributors to grow through trust, education, and authentic communication. Her work sits at the intersection of marketing, customer experience, and leadership.In this conversation, Vivienne shares a powerful firsthand account of supporting an MSP through a large scale third party data breach that impacted one hundred and thirty nine organisations.What stands out is not the technical response, but the human one.We talk about why silence is often the default advice in a crisis and why transparency, consistency, and calm communication matter more than perfect information. Vivienne explains how early and ongoing communication, dedicated support channels, and care for team mental health helped protect trust and ultimately resulted in the MSP not losing a single client.We also explore why MSP marketing and cybersecurity education are deeply connected. Vivienne challenges the industry to stop leading with products and start leading with education, particularly when it comes to AI and cybersecurity. She explains why a multi layered approach to security only works when people understand the risks, the responsibility, and the why behind the controls.Throughout the episode, we unpack the real weight MSPs carry. The sensitivity of the data we hold. The reputational impact of incidents. And the reality that leadership is tested most in moments of uncertainty.This is a candid and deeply human conversation about trust, transparency, and what good leadership looks like when the pressure is highest.If you are an MSP owner, leader, or service delivery professional responsible for client trust and team wellbeing, this episode is essential listening.Listen to this episode and explore more Ctrl Alt Deliver conversations at https://www.ctrl-alt-deliver.blog/episodesExplore more about Vivienne Winborne and One Little Seed https://www.onelittleseed.com.au

  16. 23

    Are You Still Waking Up With the Same Energy? with Zhaun Bhana

    Welcome to Ctrl Alt Deliver: MSP Service Delivery Mastery. 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.Over that time, we learned something fundamental. Great service delivery isn’t just about technology or growth. It’s about leadership, clarity, and knowing when it’s time to evolve.In this episode, we’re joined by Zhaun Bhana, a long time MSP leader who spent more than two decades building Leap Consulting into one of Perth’s standout MSPs before stepping into his next chapter in the industry.Zhaun has lived the full MSP journey from scaling and mergers to ownership stress to exit and life after the business. Today, he works closely with MSP owners across Australia, New Zealand, and globally, helping them navigate growth, consolidation, and transition with clarity and perspective.In this conversation, Zhaun challenges MSP leaders to ask a question many avoid. Are you still waking up with the same energy you had five years ago?We explore founder burnout, identity, and the hidden danger of staying in a business out of obligation rather than purpose. Zhaun shares why value breaks down when customers can’t clearly see differentiation, why MSPs that look the same end up competing on price, and why innovation that looks identical isn’t innovation at all.We also unpack what really goes wrong during MSP acquisitions, why the second acquisition is often the most dangerous, and how customer experience is shaped far more by relationships and communication than by tools or contracts.This episode is a candid, human conversation about leadership energy, value creation, and what it really means to lead an MSP through change, whether that change is growth, consolidation, or deciding what comes next.If you’re an MSP owner questioning your direction, your energy, or your long term path, this conversation will resonate.Listen to this episode and explore more Ctrl-Alt-Deliver conversations at https://www.ctrl-alt-deliver.blog/episodesExplore more about Zhaun Bhana Learn more about Evergreen and MSP M and A insights https://www.evergreensg.com/

  17. 22

    Karl Palachuk on Trust, Loyalty, and The Christmas Party Test

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery. 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.Over that time, we learned something fundamental: Great service delivery isn’t built on tools alone. It’s built on trust, consistency, and relationships that last.In this episode, we’re joined by Karl Palachuk ,one of the original architects of the managed services model and a trusted voice in the MSP industry for nearly three decades.Karl has built and sold MSPs, advised thousands of service providers, and written more than 25 books on how to deliver IT services in a way that is profitable, predictable, and sustainable. Long before “MSP” became a buzzword, Karl was helping the industry define what good service delivery actually looks like.In this conversation, Karl reminds us that MSPs don’t do business with contracts or technology, we do business with human beings.We talk about why the strongest client relationships are built on genuine connection, why the best clients actually want you to succeed, and why loyalty isn’t created through heroics, but through consistency and trust over time.Karl shares why customer service should never be a department, why process and discipline protect relationships, and why managed services remain the foundation that allows MSPs to evolve — even as AI, cloud, and new technologies continue to emerge.And yes, we talk about the ultimate test of service delivery success: knowing you’re in the right place when you’re invited to the Christmas party.This episode is a reminder that while technology continues to change, the fundamentals of service delivery do not. If you want clients who stay, teams who thrive, and a business that lasts, this conversation will resonate.Listen to this episode and explore more Ctrl-Alt-Deliver conversations at: https://www.ctrl-alt-deliver.blog/episodesExplore more from Karl PalachukLearn more about Karl’s work and access his books and resources:https://store.smallbizthoughts.com/Discover Relax, Focus, Succeed: https://relaxfocussucceed.com/Listen to The Killing IT Podcast: https://podcasts.apple.com/au/podcast/the-killing-it-podcast/id1463295432

  18. 21

    A Deep Dive with Jeni and Nick on Transparency, Focus, and Trust

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery.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.And here’s what we learned along the way:Great service delivery isn’t about working harder or being more reactive. It’s built on visibility, discipline, focus, and leaders who understand how to balance people, process, and customer expectations.This episode is a little different. It’s just Nick and me behind the microphones.In this Deep Dive, we reflect on key moments from past Ctrl-Alt-Deliver conversations and unpack the ideas that made us stop and rethink how service delivery really works inside an MSP.We talk openly about the hidden cost of poor time visibility, why overwork often goes unnoticed until it becomes resentment, and why technicians should never be left to decide what is or isn’t billable. We explore how lack of focus creates complexity, slows delivery, and damages customer trust.We also dive into why marketing often fails MSPs when it isn’t aligned with real delivery experience, and how testing your own business as a customer can reveal gaps no dashboard ever will.Throughout the episode, we share real stories from our own MSP journey, including mistakes we made, lessons learned the hard way, and the changes that had the biggest impact on service consistency, team wellbeing, and client relationships.This is an honest, practical conversation for MSP leaders who want to improve service delivery without relying on heroics, burning out their teams, or overpromising to clients.In this episode, we talk about: Why transparency around time and capacity protects both teams and clientsThe real cost of overwork and why it often goes unseen Why technicians should never decide what gets billedHow focus and standardisation improve service qualityWhy MSPs cannot be everything to everyoneThe danger of marketing that promises more than delivery can supportHow to test your own MSP as a customerWhy collaboration and partnerships matter more than everLessons learned from projects that blew out and acquisitions that didn’t go to planWhat we would do differently if we were building an MSP todayIf you’re serious about strengthening service delivery, building trust with your clients, and creating a business that scales without chaos, this Deep Dive will resonate.Listen to this episode and explore more Ctrl-Alt-Deliver conversations athttps://www.ctrl-alt-deliver.blog/episodes

  19. 20

    Delano Collins: Why MSP Service Shouldn’t Depend on Geography

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery.I’m Jeni Clift, joined by my husband and business partner Nick. Together, we spent nearly 30 years building, scaling, and eventually exiting our own MSP business.And here’s what we learned along the way: Great service delivery isn’t defined by tools or technology alone — it’s built on clarity, communication, leadership, and people who understand how to deliver value consistently.In this episode, we’re joined by Delano Collins, Chief Operating Officer at Electronic Office, and a seasoned MSP and cybersecurity leader with more than 25 years in the industry.Delano brings a rare perspective shaped by every angle of the MSP ecosystem — from early break-fix days, to scaling large MSP operations, to vendor-side experience at ConnectWise, and now executive leadership overseeing modern service delivery at scale.Throughout the conversation, Delano challenges some of the most common assumptions MSPs still hold — particularly the idea that great service depends on being physically onsite. Instead, he makes a compelling case for designing services that work anywhere, without losing the human connection customers value most.Delano shares practical insights on leadership, operations, communication, and the role AI must play in modern service delivery — not as a replacement for people, but as a way to protect customer experience, consistency, and margin.This is an episode for MSP leaders who want to scale without becoming reactive, impersonal, or overly dependent on heroics.In this episode, we talk about:Why great MSP service should not depend on physical presenceDesigning service delivery models that work anywhereDelano’s journey from break-fix IT to COO of a modern MSPThe transition from CIO to COO — and why operations is where everything meetsWhy MSPs are customer service businesses firstThe importance of communication over metrics aloneAsking the simplest question that reveals the most: “How are we doing?”Creating healthy friction to surface service issues earlyWhy progress matters more than perfection in leadershipCoaching teams under pressure and building trust when mistakes happenHow AI can help prevent service failures before CSAT dropsUsing dashboards, automation, and data to improve accountability — not micromanageWhy MSPs must stop thinking they are geographically “landlocked”How consistent service delivery creates stronger customer relationshipsDelano’s personal story — and the experiences that shaped how he leads todayDelano’s insights are grounded, honest, and deeply relevant for MSPs navigating growth, complexity, and change.If you’re serious about building service delivery that scales — without losing trust, judgement, or humanity — this episode will challenge how you think about your business.🔗 Connect with Delano Collins👉 Follow Delano Collins on LinkedIn: https://www.linkedin.com/in/delanocollins/👉 Learn more about Electronic Office: https://www.electronicoffice.net/🎧 More Ctrl-Alt-Deliver episodes: https://www.ctrl-alt-deliver.blog/episodes

  20. 19

    Empowerment, AI, and the Future of Service Delivery with Patrick Burns

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery.I’m Jeni Clift, joined by my husband and business partner Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.And here’s what we’ve learned along the way:Great service delivery is built on clarity, consistency, human connection — and leaders who know how to empower their teams.In this episode, we’re joined by Patrick Burns, CEO of Dispatch, former SVP of Product at ClickSoftware, and a key figure in shaping how MSPs and service organisations work at scale during his 11 years at Autotask.Patrick brings a perspective few leaders have — decades spent building platforms that support thousands of service teams, combined with deep experience navigating the evolution from high-touch personal service to modern, scalable service delivery.He shares insights that are practical, honest, and deeply relevant to MSPs right now.Patrick talks about what real empowerment looks like on the frontline, why rigid policies kill customer experience, and how AI is reshaping the future of service delivery (but only for those who know how to use it). His leadership lessons come not from theory, but from years spent listening to customers, building teams, and developing products used by MSPs around the world.This is the episode for every MSP leader who wants to scale without losing the humanity, trust, and judgement that great service is built on.In this episode, we talked about:The early days of Autotask and the insights that still apply to MSPs todayWhy platforms succeed when they stay close to customersPatrick’s philosophy on policies: “They should guide — not restrict.”Why empowered frontline teams deliver better service than any rulebookHow AI will reshape service — and why it will replace people who don’t use itLessons from scaling SaaS products used by thousands of MSPsWhat MSPs misunderstand about flexibility, configurability, and “best of breed” toolsThe difference between agility (enterprise) and flexibility (SMB/MSP)Why understanding your data is non-negotiable for future successThe hidden power of customer relationships — and why great salespeople create customers who feel they made the best decision of their livesWhat Zappos taught the world about exceptional customer servicePatrick’s personal journey: from the dawn of the internet to leading a modern service platform at DispatchPatrick’s stories, insights, and leadership lessons will challenge the way you think about service delivery — and might just reshape how you lead your team.🔗 Connect with Patrick Burns👉 Follow Patrick Burns on LinkedIn: https://www.linkedin.com/in/patrick-burns-b7649a1b/👉 Explore Dispatch: https://www.dispatch.me🎧 More episodes: https://www.ctrl-alt-deliver.blog/episodes

  21. 18

    techENVY’s Growth Playbook: Clarity, Consistency & Customer Experience with Anthony Quaresima

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery. I’m Jeni Clift, joined by my husband and business partner Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.And one thing has become clear along the way: Delivering great service isn’t just about technical capability, it’s about clarity, consistency, and building relationships that actually mean something.In this episode, we’re joined by Anthony Quaresima, Founder and Managing Director of techENVY, and a seasoned MSP leader with more than 20 years in the industry.Anthony brings a rare dual perspective: the depth of someone who spent decades working inside a fast-growing MSP, and the hunger of a founder who built his own business from the ground up. His insights are honest, practical, and exactly what modern MSPs need to hear.Anthony talks about what most MSPs overlook when scaling, why minimum standards matter more than ever, and how to create a customer experience that feels proactive instead of reactive.This is the episode for every MSP leader who wants to build something sustainable, not just big.In this episode, we talked about:The reality of starting a new MSP today (and why the hardest part isn’t technical)How Anthony rebuilt his entire operational foundation from scratchWhy “personable beats technical” every single timeSetting minimum standards & protecting client relationshipsThe debate between contracts vs. no lock-ins — and which path he choseWhy MSP founders must decide what they don’t do just as much as what they doThe mindset shift from employee to owner — and why it changes everythingHow techENVY uses structure, clarity, and consistent delivery to scale sustainablyAnthony’s journey — from IT shop work experience to leading a modern, fast-growing MSP — is filled with lessons, laughs, and the kind of honesty that makes every MSP rethink their foundations.👉 Follow Anthony Quaresima on LinkedIn: https://www.linkedin.com/in/aquaresima/ 👉 Follow techENVY on LinkedIn: https://www.linkedin.com/company/techenvy/ 🌐 Visit techENVY: https://www.techenvy.com.au 🎧 Explore more Ctrl-Alt-Deliver episodes: https://www.ctrl-alt-deliver.blog/episodes

  22. 17

    Amy Babinchak on Conversations, Clients, and the Coming AI Wave

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery.I’m Jeni Clift, joined by my husband and business partner Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.And one thing became clear along the way:Delivering great service isn’t just about the tools you use — it’s about curiosity, communication, and understanding the people behind every issue.In this episode, we’re joined by Amy Babinchak — a Microsoft MVP (18 times over), former MSP owner, industry educator, and one of the most trusted voices in the service provider community.Amy brings a sharp perspective and a whole lot of heart as she shares what too many MSPs are missing: meaningful conversations with clients. Why? Because without them, we can’t be proactive. We can’t lead. And we certainly can’t build the kind of trust that keeps clients around.👉 This is the conversation every MSP leader needs to hear — whether you’re just starting out or wondering what comes after the exit.💡 In this episode we talked about:Why so many MSPs fail to really talk to their clients (and what it’s costing them)How AI opens the door to deeper, more strategic conversationsWhat no one tells you about selling your MSP — until you do itThe difference between “supporting the issue” and supporting the personLetting go of vanity metrics and showing up where it really mattersWhy trust looks like being invited to the client’s Christmas partyAmy’s story — from burnout to business builder to industry mentor — is packed with lessons, laughs, and the kind of wisdom that sticks with you.👉 Follow Amy Babinchak on LinkedIn: https://www.linkedin.com/in/amybabinchak/🌐 Learn more about Third Tier: https://www.thirdtier.net/🎧 Explore more Ctrl-Alt-Deliver episodes: https://www.ctrl-alt-deliver.blog/episodes

  23. 16

    The Customer’s Customer: Guy Newton on Service That Actually Matters

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery. I’m Jeni Clift, joined by my husband and business partner Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.And one thing became clear along the way: Delivering great service isn’t just about the tools you use — it’s about curiosity, communication, and understanding the people behind every issue.In this episode, we’re joined by Guy Newton — a leader who has worked across every corner of the technology world: break-fix, local government, MSP leadership, and now Salesforce project delivery at SalesFix.Across all of it, Guy has carried one philosophy:👉 Ask questions first. Understand deeply. Serve beyond the ticket.It’s this mindset that shaped his career — and transformed how he thinks about customers, teams, and the real impact of service.💡 In this episode:Why curiosity is the most underrated skill in service deliveryThe mindset shift from “fixing problems” to supporting the customer’s customerSetting expectations before they’re set for youThe human layer behind every ticket (and why empathy still wins)Leadership lessons from MSPs, government, and project deliveryHow asking better questions leads to better outcomes — every timeGuy’s story is proof that when you slow down, stay curious, and truly understand the people you’re serving, you create service experiences that go far beyond the technical fix.👉 Follow Guy Newton on LinkedIn: https://www.linkedin.com/in/guy-newton-72697b113/ 🌐 Learn more about SalesFix: https://www.salesfix.com.au/🎧 Explore more Ctrl-Alt-Deliver episodes: https://www.ctrl-alt-deliver.blog/episodes

  24. 15

    Leading Together — Anna & Liam Furlong on Business, Balance, and Empathy

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery. I’m Jeni Clift, joined by my husband and business partner Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.We learned that delivering great service isn’t just about technology — it’s about people, culture, and how you lead when things get tough.In this episode, we’re joined by Anna and Liam Furlong, the husband-and-wife duo behind The Virtual IT Department — an MSP built on empathy, trust, and shared leadership.Together, they’ve navigated business growth, an acquisition, and the challenges of leading a team while raising a family — all while staying true to their values and to each other.💡 In this episode:How empathy and authenticity became their customer-service superpowerHiring for heart — “the stripes on the tiger, not the tricks they can pull”Creating culture that celebrates people, not just performanceTackling tough client moments with honesty and careThe reality (and reward) of building a business with your partnerAnna and Liam’s story is proof that when you lead with purpose, put people first, and share the load, you can build not just a successful MSP — but a partnership that lasts.👉 Follow Anna & Liam Furlong on LinkedIn 🌐 Learn more about The Virtual IT Department: https://itdepartment.com.au/🎧 Explore more Ctrl-Alt-Deliver episodes: https://www.ctrl-alt-deliver.blog/episodes

  25. 14

    Kultar Khatra: Leading with Empathy and Calm Leadership

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery. I’m Jeni Clift, joined by my husband and business partner Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.We learned that delivering great service isn’t just about technology — it’s about people, culture, and how you lead when things get tough.In this episode, we’re joined by Kultar Khatra, who’s taken a unique journey through the MSP world. Starting out on the vendor side, Kultar helped service providers grow and succeed before stepping into MSP ownership himself. That shift gave him a fresh perspective on what real partnership and great service look like from both sides of the channel.Kultar shares how empathy, calm leadership, and a clear sense of purpose have shaped his team culture at Crash Technology — and how helping his people understand why they do what they do has transformed the way they serve clients.Here’s what we cover in this episode: 💡 How empathy and accountability drive stronger customer relationships 💡 Why helping your team understand the why changes everything 💡 The power of staying calm, clear, and connected under pressure 💡 What true vendor-MSP partnerships look like when built on trust and careWhether you’re leading a growing MSP or managing a service team, this episode will inspire you to slow down, lead with empathy, and build a culture that truly connects.🎧 Explore other Ctrl-Alt-Deliver episodes: https://www.ctrl-alt-deliver.blog/episodes                                                                                                          🔗 Follow Kultar Khatra on LinkedIn: https://www.linkedin.com/in/kultarkhatra 🌐 Visit Crash Technology: https://www.crashtechnology.com.au/

  26. 13

    Reflections on Service Delivery: Nick & Jeni Clift on Lessons That Shaped Ctrl-Alt-Deliver

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery. I’m Jeni Clift, joined by my husband and longtime business partner, Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.This episode is a little different — it’s just the two of us behind the microphones. We’ve revisited some of our favourite Ctrl-Alt-Deliver conversations and unpacked the big ideas that truly stuck with us — the lessons that continue to shape how we help MSPs strengthen their operations and elevate client experience.Here’s what we explore together:💡 The hidden cost of overwork — and why timesheet transparency builds trust. 💡 Why the best MSPs act like a farm shop, not a supermarket. 💡 How aligning marketing promises with delivery creates genuine client loyalty. 💡 What really makes an acquisition work — from people to process to purpose.It’s an open, honest look at the realities of growing a service-focused business and the habits that make lasting success possible.🎧 Listen to other Ctrl-Alt-Deliver episodes: https://www.ctrl-alt-deliver.blog/episodes👉 Connect with Nick Clift on LinkedIn: https://www.linkedin.com/in/nick-clift-mspcoach-mentor-eosintegrator/                                                                                    🌐 Learn more and master your MSP: https://www.tenassia.com

  27. 12

    Dean Calvert on Letting Go, Leading with Empathy, and Building a Business That Can Fly Without You

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery. I’m Jeni Clift, joined by my husband and longtime business partner, Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.This week, we sit down with Dean Calvert — Founder of Calvert Technologies, Professional EOS Implementer, and Flight Instructor — to explore what it really takes to build a business that runs smoothly, serves people well, and eventually thrives without you at the helm.Dean shares lessons from 30 years in the MSP world, from humble beginnings in Adelaide to a successful acquisition and a new chapter helping other business owners find clarity and balance. Along the way, he reveals why control, communication, and culture matter far more than tools — and how empathy can transform both leadership and customer service.Here’s what we cover together: ✅ Why you should always know your next chapter before exiting your business ✅ How to build trust and independence within your team ✅ The true meaning of customer service — and why empathy always wins ✅ What aviation taught Dean about leadership and letting go“Your job as a leader isn’t to hold the controls forever — it’s to help others fly safely without you.” — Dean Calvert👉 Connect with Dean on LinkedIn: https://www.linkedin.com/in/deancalvert🌐 Learn more about Calvert Technologies: https://www.calvert.net.au🎧 Listen to this and more episodes on Ctrl-Alt-Deliver: https://www.buzzsprout.com/2514171/episodes🌐 Explore the full archive: https://www.ctrl-alt-deliver.blog/episodes

  28. 11

    Greg Sharp on Agreements, Growth, and Building Real Value in Your MSP

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery.I’m Jeni Clift, joined by my husband and longtime business partner, Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.Over those years, we learned that great service delivery isn’t just about technology, it’s about how you lead, communicate, and build trust with your clients.In this episode, we sit down with Greg Sharp, CEO and Founder of ZenContract, and a leader who’s helped hundreds of MSPs bring structure, protection, and professionalism to the way they work.After building and selling his own MSP, Base 2, for a 10× multiple, Greg turned his hard-won lessons into a mission: helping MSPs use clarity, consistency, and automation to strengthen client relationships and safeguard their businesses.Here’s what we covered together: ✅ Why “agreements” are about partnership, not lock-in ✅ How better systems and contracts can increase business value ✅ The painful mistake that inspired ZenContract and how it’s helping MSPs scale smarter ✅ What every MSP should do years before they plan to exit🎧 Listen in for real-world lessons on growth, leadership, and protecting the business you’ve worked so hard to build.👉 Connect with Greg on LinkedIn: Greg Sharp🌐 Learn more about ZenContract: https://www.zencontract.com🎧 Listen to this and more episodes on Ctrl-Alt-Deliver: https://www.buzzsprout.com/2514171/episodes🌐 Explore the full archive: https://www.ctrl-alt-deliver.blog/episodes

  29. 10

    AI, Speed, and Sales: James Vickery on What Really Separates High-Performing MSPs

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery. I’m Jeni Clift, joined by my husband and longtime business partner, Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.Over that time, we learned that success in the MSP world isn’t just about the latest tools or trends — it’s about dependability, culture, and the ability to keep pace with changing client expectations.In this episode, we sit down with James Vickery — CEO of Benchmark 365. From building and selling his own MSP, to pioneering global service delivery models, to now helping MSPs worldwide scale profitably, James has spent more than two decades shaping what high-performing MSPs really look like.Here’s what we covered together: ✅ Why AI is speeding up market expectations — and what that means for MSPs who can’t just “AI everything” ✅ Why dependability matters more than dashboards when it comes to long-term client retention ✅ How offshore success comes from culture, structure, and redundancy — not just cost savings ✅ The surprising truth: the only difference between a low-performing and high-performing MSP is sales ✅ Practical steps MSP leaders can take today to build scalable, resilient, and client-focused businessesWe created this podcast to share the kinds of conversations we wish we’d had more of while running our own MSP — real, practical advice from leaders who’ve been in the trenches and built businesses that last.Whether you’re leading an MSP, building global teams, or simply looking for ways to keep clients happier while scaling smarter, this episode with James Vickery is packed with insights you can put into practice right away.👉 Connect with James on LinkedIn: https://www.linkedin.com/in/jvb365🌐 Learn more about Benchmark 365: https://benchmark365.com/🎧 Listen to this and more episodes on Ctrl-Alt-Deliver: https://www.buzzsprout.com/2514171/episodes🌐 Explore the full archive: https://www.ctrl-alt-deliver.blog/episodes

  30. 9

    Happy People, Simple Systems: Brian Dosal’s MSP Lessons

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery. I’m Jeni Clift, joined by my husband and longtime business partner, Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.Over that time, we learned that delivering great service isn’t just about technology — it’s about how you build your culture, keep things simple for clients, and create accountability within your team.In this episode, we sit down with Brian Dosal — CEO of Strety and co-founder of BrightGauge. From growing up in a family MSP, to building one of the MSP industry’s go-to reporting platforms, to now leading a SaaS company focused on EOS, Brian has lived the journey from startup to successful exit and back again.Here’s what we covered together: ✅ Why MSPs are really “selling insurance” — and how to keep client reporting simple and effective ✅ How BrightGauge grew by focusing on clarity, culture, and client trust ✅ Why happy people create happy services — and how culture multiplies client success ✅ The danger of over-automation in EOS, and why accountability should always come first ✅ Practical lessons for MSP leaders who want to simplify, scale, and strengthen their business foundationsWe created this podcast to share the conversations we wish we’d had more of while running our own MSP — real, practical advice from people who’ve been through the trenches and built businesses that last.Whether you’re scaling an MSP today, building a SaaS tool, or simply want to strengthen your service delivery, this episode with Brian Dosal is packed with insights you can apply right away.👉 Connect with Brian on LinkedIn: https://www.linkedin.com/in/bdosal/🌐 Learn more about Strety: https://strety.com/🎧 Listen to this and more episodes on Ctrl-Alt-Deliver: https://www.buzzsprout.com/2514171/episodes🌐 Explore the full archive: https://www.ctrl-alt-deliver.blog/episodes

  31. 8

    Begin With the End in Mind: Kerry Boulton on Building a Business That Lasts

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery.I’m Jeni Clift, joined by my husband and longtime business partner, Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.Over that time, we learned that true success in business isn’t just about growth — it’s about building something that can thrive without you. The way you prepare for succession, transition, and even exit determines whether your business remains valuable long after you’ve stepped away.In this episode, I sit down with Kerry Boulton — Exit Strategy Coach, Value Builder, and former EOS Implementer. Kerry helps founders design businesses that are ready for any future, whether that means selling, succession, or scaling with confidence.Here’s what we covered together:✅ Why every business should be “you-proof” — able to run without the founder ✅ How to begin with the end in mind and design your business for future value ✅ The Five Ds that can force an unplanned exit — and how to prepare for them ✅ Why the most important investor in your business is you ✅ Practical steps to future-proof your business 3–5 years before sellingWe created this podcast to share the conversations we wish we’d had more of while running our own MSP — real, practical advice from people who’ve been through the journey and built businesses that last.Whether you’re years away from selling or simply want to strengthen your foundation, this episode with Kerry is packed with insights you can put into action right now.👉 Connect with Kerry on LinkedIn: Kerry Boulton 🌐 Get her book, The Uncensored Truth about Exit Strategies: Exit Strategy Group🎧 Listen to this and more episodes on Ctrl-Alt-Deliver: https://www.buzzsprout.com/admin/2514171/episodes🌐 Explore the full archive: https://www.ctrl-alt-deliver.blog/episodes

  32. 7

    From First Hello to Final Goodbye: Oscar Clift on Onboarding & Offboarding

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery.I’m Jeni Clift, joined by my husband and longtime business partner, Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.Over the years, we learned that real success in the MSP world isn’t just about the technology you deliver — it’s about how you deliver it. From first impressions to lasting partnerships, the way you onboard, support, and even offboard clients defines your reputation and growth.In this episode, we sit down with Oscar Clift, Service Delivery Manager at Morphability — and yes, our son. Oscar has grown up in the MSP space and now helps MSPs streamline operations, strengthen client relationships, and drive growth through structured onboarding and service delivery processes.Here’s what we covered together: ✅ Why first impressions — for both clients and employees — shape the success of every relationship ✅ The importance of having a written, structured onboarding plan (not just one in your head) ✅ Why MSPs should charge for onboarding to highlight its value and set clear expectations ✅ How to make offboarding smooth and professional so clients may return in the future ✅ The role of empathy, communication, and small personal touches in creating client confidenceWe created this podcast to share the conversations we wish we’d had more of while running our own MSP — real, practical advice from people who’ve lived the challenges and found better ways forward.Whether you’re onboarding your next big client, welcoming a new team member, or even navigating the exit of a long-term relationship, this episode with Oscar is packed with practical strategies you can put into action right away.👉 Connect with Oscar on LinkedIn: Oscar Clift🌐 Learn more about Morphability: https://www.morphability.au🎧 Listen to this and more episodes on Ctrl-Alt-Deliver: https://www.buzzsprout.com/2514171/episodes🌐 Explore the full archive: https://www.ctrl-alt-deliver.blog/episodes

  33. 6

    The Virtual Hug of Service Delivery: Aaron Lake on 17 Years with Imagine Now IT

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery. I’m Jeni Clift, joined by my husband and longtime business partner, Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.Over the years, we learned that real success in the MSP world isn’t just about the technology you deliver — it’s about how you deliver it. Building accountable teams, creating consistent client experiences, and knowing when to adapt your model are what keep clients loyal and your business sustainable.In this episode, we sit down with Aaron Lake, General Manager of Imagine Now IT. Aaron’s been with the company for almost 17 years, starting his tech journey in a small computer shop back in 2003 before helping shape Imagine Now IT into the service-driven MSP it is today. Along the way, he’s built teams, developed client relationships, and formed a leadership style that puts empathy and listening at the heart of service delivery.Here’s what we covered together: ✅ Why Aaron calls empathy in MSPs a “virtual hug” — and why listening matters even more than fixing the problem fast ✅ The art of teaching without “driving the mouse” — and how patience builds stronger teams and more confident clients ✅ The future of automation — what “agent-to-agent” systems could mean for MSPs, and why the human element will always be essential ✅ A practical look at balancing SLAs and client satisfaction without burning out your team ✅ What Aaron would do differently if he were starting an MSP today — and the lessons learned from nearly two decades in the trenchesWe created this podcast to share the conversations we wish we’d had more of while running our own MSP — real, practical advice from people who’ve lived the challenges and come out stronger.Whether you’re helping a stressed-out client, training your next superstar tech, or wondering how automation will change your role, this episode with Aaron is packed with insights you won’t want to miss.🌐 Learn more about Imagine Now IT: https://www.imaginenowit.com.au🎧 Listen to this and more episodes on Ctrl-Alt-Deliver: https://www.buzzsprout.com/2514171/episodes🌐 Explore the full archive: https://www.ctrl-alt-deliver.blog/episodes

  34. 5

    Trust, Care, and Community: MSP Lessons with David Bugeja

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery. I’m Jeni Clift, joined by my husband and longtime business partner, Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.What we’ve learned is this: real success in the MSP world isn’t just about the technology you deliver — it’s about how you deliver it. Building strong vendor relationships, creating consistent client experiences, and staying adaptable are what keep clients loyal and your business sustainable.In this episode, we sit down with David Bugeja, General Manager at Manage Protect. David’s career spans nearly 20 years across both MSPs and vendors, and for the past eight years he’s been helping MSPs across Australia deliver cloud solutions that are simple, secure, and truly partner-focused.Here’s what we covered together: ✅ Why the most successful MSP–vendor relationships aren’t about the cheapest product — but about trust, shared values, and growing together ✅ How David reframes AI for MSPs as a tool to give time back, not a threat to jobs ✅ Why listening — and showing partners their feedback matters — is a superpower for keeping relationships strong ✅ The “save the day” story of migrating 121 million objects and 104 TB of data to protect MSP partners from an end-of-life backup product ✅ The five core values that guide Manage Protect — and why David wishes he had a “magic button” to instantly know if new hires truly live them ✅ Why no MSP should go it alone — and how communities like SMBiT Pro, GTIA, and IT Nation give leaders the support, knowledge, and trust you can’t build in isolationWe created this podcast to share the conversations we wish we’d had more of while running our own MSP — practical advice from people who’ve lived the challenges and come out stronger.Whether you’re driving between client sites, catching up on admin, or simply curious about where the MSP industry is heading, this episode is packed with insights you can apply today.👉 Connect with David on LinkedIn: https://www.linkedin.com/in/david-bugeja-au/ 🌐 Learn more about Manage Protect: https://www.manageprotect.com/ 🎧 Listen to this and more episodes of Ctrl-Alt-Deliver here: https://www.buzzsprout.com/2514171/episodes🌐 Explore the full archive: https://www.ctrl-alt-deliver.blog/episodes

  35. 4

    Scaling Smart: How Scott Jefferis Grew an MSP from $0 to $2.4M

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery.I’m Jeni Clift, joined by my husband and longtime business partner, Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.Over the years, we learned that real success in the MSP world isn’t just about the technology you deliver — it’s about how you deliver it. Building accountable teams, creating consistent client experiences, and knowing when to adapt your model are what keep clients loyal and your business sustainable.In this episode, we sit down with Scott Jefferis, Director of Revolve IT — an MSP he co-founded in 2020 at the very start of the pandemic. In just five years, Revolve IT has grown from zero to $2.4 million, with 20% being their smallest growth year. Along the way, Scott has also expanded into managed print with the acquisition of Southern Cross Office Equipment, while staying laser-focused on client experience and sustainable scaling.Here’s what we covered together: ✅ How Scott grew Revolve IT from $0 to $2.4M in five years — and why learning from early mistakes was key to avoiding costly detours ✅ Why setting client expectations during onboarding prevents SLA chaos and keeps both profitability and satisfaction in balance ✅ The real-world challenge of ticket triage — and how Scott balances automation, AI, and the human touch to get it right ✅ Two “save the day” stories: surviving an NBN cable cut with seamless 5G failover, and doubling a client’s team in days during a cyclone response ✅ The one thing Scott would do differently if starting again today — and why processes and documentation are the unsung heroes of MSP growthWe created this podcast to share the conversations we wish we’d had more of while running our own MSP — real, practical advice from people who’ve lived the challenges and come out stronger.Whether you’re in the office, in the field, or stuck waiting for that one “quick” Windows update, this episode’s the perfect companion.👉 Connect with Scott on LinkedIn: https://www.linkedin.com/in/scott-jefferis-77808343/🌐 Learn more about Revolve IT: https://revolveit.com.au/🎧 Listen to this and more episodes on Ctrl-Alt-Deliver: https://www.buzzsprout.com/2514171/episodes🌐 Explore the full archive: https://www.ctrl-alt-deliver.blog/episodes

  36. 3

    Beyond SLAs: Practical MSP Lessons with Scott Atkinson

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery. I’m Jeni Clift, joined by my husband and longtime business partner, Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.Over the years, we learned that real success in the MSP world isn’t just about the technology you deliver — it’s about how you deliver it. Building accountable teams, creating consistent client experiences, and knowing when to adapt your model are what keep clients loyal and your business sustainable.In this episode, we sit down with Scott Atkinson, CEO of TribeTech — a modern MSP he co-founded in 2018 after decades of experience across IBM, Netforce, Dimension Data, and BigAir. Scott’s career has been shaped by building, selling, and reinventing IT businesses — and today he leads TribeTech with a bold, outcome-focused approach.Here’s what we covered together: ✅ Why TribeTech ditched traditional SLAs — and how measuring urgency by business impact creates stronger client relationships ✅ The onboarding approach that standardises client infrastructure and reduces support noise from day one ✅ The disaster recovery story of TribeTech’s Sydney office literally collapsing — and how the team kept operating the very next day thanks to a cloud-first design ✅ Why the hardest (but most profitable) decision is learning to say no to work that doesn’t fit your model ✅ Scott’s perspective on automation, AI, and the one task he wishes technology would finally solveWe created this podcast to share the conversations we wish we’d had more of while running our own MSP — real, practical advice from people who’ve lived the challenges and come out stronger.Whether you’re in the office, in the field, or stuck waiting for that one “quick” Windows update, this episode’s the perfect companion.👉 Connect with Scott on LinkedIn: https://www.linkedin.com/in/scottatkinsonau/🌐 Learn more about TribeTech: https://www.tribetech.com.au/🎧 Listen to this and more episodes on Ctrl-Alt-Deliver: https://www.buzzsprout.com/2514171/episodes🌐 Explore the full archive: https://www.ctrl-alt-deliver.blog/episodes

  37. 2

    Small, Smart, Sustainable: MSP Growth Lessons with Linden Jackson

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery. I’m Jeni Clift, joined by my husband and longtime business partner, Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.Over the years, we learned that real success in the MSP world isn’t just about the technology you deliver — it’s about how you deliver it. Building accountable teams, creating consistent client experiences, and knowing when to adapt your model are what keep clients loyal and your business sustainable.In this episode, we sit down with Linden Jackson, founder of Agile IT — an MSP he’s built and run for the past 18 years with a deliberate focus on staying lean, sustainable, and deeply connected to clients. Linden’s career spans three decades in IT, from selling photocopiers and registers to leading a small but highly effective MSP team.Here’s what we covered together: ✅ Why Linden chooses not to chase massive growth — and how designing a sustainable business lets him step away without it falling apart ✅ The simple mindset shift that makes clients feel like you’re “part of their team” instead of a faceless help desk ✅ The automation win that’s boosted consistency across his service delivery (and the one manual task he wishes could vanish forever) ✅ A hero story about rescuing a brand-new client in the middle of a critical server failure — and why the real fix had nothing to do with the part they thought they needed ✅ Linden’s honest take on what he’d do differently if starting an MSP from scratch today, from setting client expectations to hiring for listening skills, not just technical skillsWe created this podcast to share the conversations we wish we’d had more of while running our own MSP — real, practical advice from people who’ve lived the challenges and come out stronger.Whether you’re in the office, in the field, or stuck waiting for that one “quick” Windows update, this episode’s the perfect companion.👉 Connect with Linden on LinkedIn: https://www.linkedin.com/in/lindenjackson/ 🌐 Find more info about AgileIT: https://agileit.com.au/🎧 Listen to this and more episodes on Ctrl-Alt-Deliver: https://www.buzzsprout.com/admin/2514171/episodes 🌐 Explore the full archive: https://www.ctrl-alt-deliver.blog/episodes

  38. 1

    Beyond Busy: Real Service Delivery Lessons with Brendan Rose

    Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery. I’m Jeni Clift, joined by my husband and longtime business partner, Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.We learned along the way that real success isn’t just about the tools you use or the tech you know.It’s about how you deliver: building accountable teams, creating consistent client experiences, and staying adaptable — even when the industry keeps changing.For our very first episode, we wanted to open up the kinds of conversations we wish we heard more of: honest, practical, no-nonsense advice from people who’ve truly been there.So we sat down with Brendan Rose from Morphability — someone who’s seen the MSP world from every angle: starting out as employee #6 in a fast-growing MSP, working his way through roles from service manager to COO, and now helping other MSPs grow smarter (and saner).Here’s what we covered together:✅ Why engineers closing tickets silently can quietly damage client trust — and the simple fix Brendan swears by: pick up the phone ✅ How under-reporting time doesn’t just mess up your numbers — it hides the true cost, blocks your growth, and keeps your business stuck ✅ Practical tips for balancing day-to-day “busyness” with planning for the bigger clients and challenges you don’t have yet ✅ Brendan’s hero stories, lessons learned, and what he’d do differently if he built an MSP from scratch todayWe created this podcast to have real conversations — not just about what’s shiny and new, but about what actually works to build sustainable, client-focused service delivery.So wherever you’re listening from — in the car, between client visits, or on your morning walk — hit subscribe or follow so you don’t miss an episode of Ctrl-Alt-Deliver.We’re really glad you’re here.And we hope you enjoy Brendan’s insights as much as we did.👉 Connect with Brendan on LinkedIn: Brendan Rose🌐 Learn more about Morphability: https://www.morphability.au🎧 Listen to this and more episodes on Ctrl-Alt-Deliver: https://www.buzzsprout.com/2514171/episodes🌐 Explore the full archive: https://www.ctrl-alt-deliver.blog/episodes

  39. 0

    What is Ctrl-Alt-Deliver?

    Welcome to the podcast, control Alt Deliver, MSP Service Delivery Mastery. I'm Jenny Clifft and I'm joined by my husband and longtime business partner, Nick. Together we've spent nearly 30 years in the MSP industry building, leading, and eventually exiting our own MSP business. Along the way, we learned that real success in the MSP world isn't just about having great tech or the right tools.It's about how you deliver. It's about building strong, accountable teams, creating consistent client experiences, and staying adaptable in a fast changing landscape. We created this podcast to open up the kinds of conversations we wish we had more of Honest, practical, no BS insights from people who've actually been there.Each episode we'll sit down with MSP owners, industry leaders, and the occasional special guest to explore what's working, what's changing, and how to stay focused when it comes to service delivery. So whatever you are doing. Walking the dog, driving between clients or grabbing a coffee. Hit subscribe or follow and turn on notifications so you don't miss an episode of Control Alt Deliver.We are really glad you're here. 

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ABOUT THIS SHOW

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.

HOSTED BY

Jeni Clift, Nick Clift

CATEGORIES

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