Thinking Out-Of-The-Box Every Day
Out-of-the-box thinking is about finding practical solutions to problems, using logic and experience to understand the issues vs. believing technology can solve them. It's about being practical.
While my MSP experience has made me an IT Generalist spanning multiple industries, it has also prepared me to be an IT Leader, capable of solving business issues. Everyone's talking about Cybersecurity and AI, but implementing them effectively requires understanding both the technology and the business context.
Tech is not always the answer, but practicality is, and that is what I bring to the table.
This is my Great Dane, Zoey. She is playful, loyal, and a fantastic reminder that technology is not life. She tells me, “Get up. Let’s go for a walk.”
She reminds me to be real, practical, and have fun once in a while.
Over 25+ years as an IT Professional
Everyone has a career history and I'm no different. Humble beginnings as a helpdesk technician at Uniserve Online signing up users and assisting with troubleshooting modem connectivity, issues with Eudora, or Netscape, etc. Eventually moving on to Wavepoint Solutions, driving around the Fraser Valley visiting client sites, setting up networks, servers, workstations, and providing hands-on help with common and uncommon issues. Transitioning to what's more familiar today, the Managed Services Provider, expanding clientele and working more efficiently, taking on bigger and more complex projects as a Solutions Provider, then a upwards move to a larger, more established MSP, Sea to Sky Network Solutions.
Having never specialized in any single technology, I've become something of a tech-expert on everything, with an in-depth knowledge of how tech just works. The MSP exposure is very much being thrown into the deep end, repeatedly, always with different challenges, and sink or swim. After 20 years, in multiple industries (Transportation & Logistics, Construction, Healthcare, Food, Farm Equipment, Manufacturing, Municipal Management, Accounting, Law) where no two organizations operate the same, or have the same software stack, I've gotten pretty good at recognizing common challenges, including those relative to each sector or industry. For instance, Office 365 for Municipalities isn't that much different from a Lawyer's office but ERP implementation for one company can be vastly different to another. However, while the layering of the technologies vary, the underlying components are almost always the same, and the issues and challenges remain pretty consistent.
And I'm more than just technical knowledge. Success over the years has taught me to be a great interpreter and communicator; being able to understand the issues non-technical people are having, converting to a technical understanding, and back again. To expand on this communication to mentor other technicians, provide clear direction, and always a focus on efficiency and objectivity. Sure, solve the immediate issue, but always go deeper - look for root causes and solve those, too. Whether leading a team or interfacing with Vendor Support, the objective is always the same - get it implemented, get it working, and get it working well.
I can step into virtually any technical role and own it, but my particular skillset is to be a Tech Leader. IT Management, Architect, Solution Designer, all rolled into one.
Flexibility
Technology changes constantly. Windows Server 2025 didn’t exist when I started managing infrastructure. Linux wasn’t friendly. Azure didn’t exist. Microsoft 365 didn’t exist. Half the tools I use daily now weren’t even concepts 10 years ago.
But business needs? Those are remarkably consistent. Uptime. Security. Productivity. Cost control. Communication. Collaboration.
The best IT professionals don’t chase every new technology—they stay flexible enough to evaluate what’s worth adopting and what’s just noise. I’ve migrated clients from on-premises to cloud, from Exchange to M365, from physical to virtual to hybrid. Not because it was trendy, but because it solved real problems.
Flexibility means knowing when to embrace new technology and when to maintain what works.
Agile Approach
I don’t just implement solutions—I partner with stakeholders to understand what success looks like, then build technology that enables it. That means being flexible enough to adapt when requirements change (and they always do), while pragmatic enough to choose the right tool over the trendy one, and honest enough to say “that won’t work” when something doesn’t serve the business need.
Real agility isn’t about methodology frameworks—it’s about understanding the problems well enough to solve them efficiently, even when the problem changes halfway through.
Ethos
I’ll absolutely put in the long hours when something’s genuinely critical—I’ve done enough 3am troubleshooting sessions to know that sometimes there’s no substitute for grinding through a problem until it’s solved. But I refuse to keep fighting the same fires. If something breaks repeatedly, I’m going to spend the time to fix it permanently—whether that means writing automation scripts, building better monitoring, implementing proper processes, or just documenting the solution so the next person doesn’t start from scratch. Work hard when needed, but always ask: “How do I make this easier next time?”
That’s what 25 years has taught me—the difference between being busy and being effective.
Efficient Mindset
When something breaks repeatedly, most people optimize the fix. They get faster at applying the patch, streamline the workaround, document the procedure. I do the opposite—I stop accepting that it should break at all and fix whatever’s causing it at the root.
This is systems-level thinking. A user can’t access a file share? Sure, I can reset permissions. But why did permissions break? Bad inheritance structure? Manual changes instead of group policy? No access management process? The efficient solution isn’t faster permission fixes—it’s rebuilding identity and access management so permissions don’t randomly break.
I’ve spent 25 years learning to recognize patterns: when individual problems are actually symptoms of systemic issues. Multiple clients having email deliverability problems? That’s not a string of unrelated tickets—that’s inadequate SPF/DKIM/DMARC implementation across the environment. Recurring security incidents? Not individual user mistakes—that’s insufficient identity governance and conditional access policies. Solve the big architectural problem, and dozens of small operational problems disappear automatically. That’s true efficiency.
What Can Jason Zondag Do?
As an IT Generalist I have a lot of experience with a lot of different things. Obviously, some more than others. Working most of my career with Managed Service Providers, I would be thrown in to the deep end and forced to just 'figure it out' to initially fix the issue, then do a deep dive to understand the root cause. This is an education in the field, usually the most valuable education possible.
Critical Thinking | IT Service Delivery & Governance | Advanced MSP Practitioner | Endpoint Management (Intune/Autopilot/MDM) | Microsoft 365 | Azure | Endpoint Protection (XDR) | Advanced Troubleshooting | Communications | Linux | Automation | Networking | Active Directory | Entra ID (RBAC, IAM) | Conditional Access | Virtualization | VMware | Proxmox | Hyper-V | IT Management | Vendor Management | Project Management | DNS | Cybersecurity | Backup & Disaster Recovery | Compliance | DHCP | Infrastructure | AVD/VDI | Azure | System Design | System Architecture | Solution Provider | Documentation | Policy Development | Group Policy | Windows Server | Windows Workstation | IIS | Optimizations | Process Review | Efficiency | Mentoring
Current Projects
Lately I've been learning the ins and outs of AI. Locally hosted AI models such as Qwen, Llama, and Dolphin. This is a setup of Docker and Docker networking, integration with API, and even locally linking to AI Image Generation. Fascinating stuff you can do from the comfort of your home lab!
I am always learning; always building.
I maintain a production-grade (but non-production) home lab that probably rivals most SMB environments:
- Proxmox cluster with quorum
- Active Directory domain environment synced to an Azure/Entra ID tenant
- Docker infrastructure running AI/ML containers (Ollama, ChromaDB, OpenWebUI)
- Redhat, CentOS, Debian, Ubuntu
- Multi-VNET Azure subscription,
- Enterprise networking gear
- Multi-TB storage and Backup
- Plesk Web Services
I use this environment for continuous learning. for pre-production testing, skill development, and exploring emerging technologies before they hit mainstream adoption. Current focus: local AI infrastructure, containerization, and automation workflows.
Professional Project Experience:
Over 20 years, I've led infrastructure overhauls for municipalities, architected Azure migrations for 30+ server environments, resolved impossible troubleshooting challenges that stumped entire teams, and designed solutions that nobody else saw because they required reframing the problem entirely.
The constant theme: critical thinking applied to real-world constraints. Finding practical solutions when the "obvious" approach won't work.
Want specifics? Let's talk.
Things I've learned...
I've been documenting fixes to uncommon issues for ages now. I recently started a new site to share and collaborate with with colleagues.
Some are common things that you may not do a lot and may have a bunch of steps with a gotcha here or there (getting it right the first time saves a ton of time and grief). Some are tricks I've learned and documented so I wouldn't forget.
Speak With Me
Want to talk about a project or position you may be interested in hiring me for?
jason@zondag.ca
Call
+1.604.825.6792
Time Zone
Americas/Vancouver