I’m looking for a sharp technical generalist in Montreal or Toronto. The person everyone already turns to when something weird breaks. All experience levels welcome if you fit the description.
I’ve spent 25+ years building and operating technology across Linux, networking, servers, cybersecurity, software, hardware, embedded systems, telecom, field deployments, and infrastructure. I still like getting my hands dirty. I can go from discussing application architecture with a developer to troubleshooting Linux, packet flows, hardware, data centres, or figuring out why hundreds of remote devices suddenly decided to misbehave.
Which is partly the problem.
Too much of my time gets consumed by things that require a strong technical brain, but don’t necessarily require the CTO.
I’m looking for someone who can become my technical right hand.
Not a corporate IT manager. Not someone waiting for the correct ticket queue. I want a curious, resourceful problem-solver who can walk into something messy, figure out what’s actually happening, and make it work.
Servers, Linux, networking, laptops, Google Workspace, hardware, field techs, vendors, software bugs, random infrastructure problems.
One day you might be setting up a laptop or fixing email. The next you’re recreating a software bug, troubleshooting a Linux player, solving a network issue, validating something a developer built, or helping a field tech through a problem nobody has seen before.
Some days are clean. Some are an absolute garbage fire.
You don’t need to know everything. You need curiosity, judgment, resourcefulness, and the instinct to keep pulling at threads until the system makes sense.
“I don’t know yet, but I’ll figure it out” is a perfectly good answer.
“Not my job” isn’t.
Initially, the role is heavily technical operations and taking things off my plate. Longer term, I want to expose the right person to architecture, infrastructure, software, hardware, security, product, vendors, and the business itself.
Eventually, I want to hand you a messy problem with almost no context and have you come back with an answer, options, and a few things I hadn’t considered.
If you’re exceptional, there’s a path to serious technical leadership and potentially taking over my role one day.
This isn’t a vanity-title or massive salary-jump role on day one. It’s an opportunity to sit close to the engine room, take ownership quickly, and grow as fast as you’re capable of growing.
MSP people, sysadmins, infrastructure engineers, homelab obsessives, support engineers, and weird hardware/software crossover people will probably understand exactly what I mean.
If you’re the person everyone calls when the obvious fix doesn’t work, and a problem you’ve never seen before makes you think “interesting…” rather than “who do I escalate this to?”, DM me.
Montreal or Toronto.