What is My IT Guy?

My IT Guy is an established Managed IT Services provider that works with a wide variety of clients, providing all facets and functions of a typical “enterprise IT Department”, but tailored for small- and medium- sized business in and around Kitchener, Waterloo, Cambridge, Guelph, Milton, and surrounding areas.

Our consistent growth since 2004 speaks volumes about our ability to work as a collaborative team, focus on what we do best, and consistently foster a culture of learning and knowledge sharing.

We are looking for the right individual to grow with us, and we are offering:

  • Competitive Salary,
  • Flexible work hours,
  • Flexible work-from-home options (fully remote, hybrid, and in-office are all possible),
  • Company paid benefits,
  • The chance to work with some truly amazing peers!


Who is My IT Guy?

We believe our shared values and behaviours are instrumental to what makes us a great team:

  • Inclusive Collaboration: Helping our teammates wherever we can, and being able to draw from our broad pool of collective experience, builds confidence and trust in what makes our amazing, diverse team so capable and effective. Teaching, learning, sharing, and coaching are ongoing.
  • Integrity & Accountability: We owe each other and our clients better than “close enough”, so we strive to do things “the right way”. Of course, we also know that everyone makes mistakes, so practicing blameless problem-solving is key, and requires that we’re all respectful in how we engage with each other, and that we are open to accepting that we may not have all the answers, and must be open to new ideas or new ways of doing things.
  • Growth Oriented: We believe every member of our team should be working to better themselves, incrementally, always. This might mean acknowledging our areas of improvement, taking action to address them, and stepping out of our comfort zones to take on new challenges.
  • Considerate: We believe that everyone is deserving of thoughtful consideration, without judgement or defensiveness. If an issue arises, we listen, reflect, and respond constructively.
  • Clear & Concise Communication: Ideas and instructions should always provide context and clarity, free of jargon, that’s easy for anyone to understand.


Who are you?

Our ideal candidate exemplifies our shared values, and would also describes themselves as:

  • Well liked! You’re a good listener with experience navigating people’s concerns in a positive, receptive, and constructive manner. You comfortably relate with co-workers and clients alike, and you do your best to help where you can.
  • An adaptable, life-long learner: We are constantly growing and learning new and better ways to operate. If that doesn’t excite you, you should look elsewhere.
  • Possessing flexible organizational skills to ensure deadlines are met, and tasks are completed with minimal supervision, while also able to pivot and reprioritize when necessary
  • Attention to detail and a desire to do things “the right way” is important to you.



Our ideal candidate will be comfortable with most functions performed by a typical systems administrator:

  • Microsoft 365 (Exchange, Teams, SharePoint, OneDrive, etc), migrations to/from, configuring for security, day-to-day management, and helping clients get the most value out of these services
  • Azure Active Directory and Endpoint Manager (MFA, Conditional Access, MDM, AutoPilot, etc)
  • Sophos & Ubiquiti networking (deployment & management)
  • Troubleshooting Windows 10, Windows Server 2016+, and network issues
  • Setting up servers and desktops, installing applications, migrating client data, and ensuring our clients are happy and comfortable with the new environment
  • Organizing themselves to efficiently and effectively help clients with their technical issues, while keeping detailed notes about what was done and what’s next, and scheduling tasks as needed to meet or exceed deadlines, in ConnectWise Manage (or similar Ticketing systems)
  • Thoroughly documenting clients’ systems and processes in ITGlue (or similar documentation platforms)
  • Occasional after-hours/on-call support: We believe everyone is entitled to a healthy work/life balance, so when necessary, after-hours work is planned well ahead of time, and emergency calls are rare.



  • Experience with all the above responsibilities
  • At least 4 years in support and project roles at a Managed Service Provider
  • Able to communicate fluently in English both verbally and through written communication
  • Knowledge and experience with Apple products would be an asset


Now what?

Does this sound like you? Are you excited to join the My IT Guy team?

We're hiring big thinking detectives!

Join a Growing Company

My IT Guy has grown every year since it was established in 2004, continuing our growth even through the worst of the 2008 recession and the global pandemic. Our growth speaks volumes about our ability to work as a collaborative team, focus on what we do best, and consistently foster a culture of learning and knowledge sharing.

With Long-term Vision

As we grow, promoting people from within the company to new positions will be the best way to move forward. To do this we will be committed to finding the best and brightest people and do everything we can to help them succeed within the company.

Where You Can Make an Impact

You never know where the best ideas will come from, and we believe in keeping everyone involved in the business. Being a part of My IT Guy means you will have a real, measurable influence on how the company grows and what strategic direction we take.

Does this sound like you? Are you excited to join the My IT Guy team?