Technical Support & IT Systems Administrator

About Us

At Port 443 we work together, laugh together, and eat a lot of donuts together. (Have you seen our Instagram? It’s basically a food blog.) 

Our products (My Music Staff, TutorBird & AthletaDesk) are always evolving, making for an exciting and dynamic environment. Every day, we’re connecting with thousands of users all around the world. If you ask what they love about us, they’ll tell you that we really listen to their needs and go above and beyond to help them. Our members are at the heart of everything we do. Their feedback and ideas help to shape our products, and at the end of the day, we’re here because of them… 

…and because of the donuts. 

About You

You’re a customer-focused IT Systems Administrator with strong communication skills that can explain technical concepts with simplicity and clarity (meaning you can take computer speak and translate it into human speak!). You’re friendly, patient, and willing to jump in to help a teammate who needs it. You’re flexible and always ready to hit the ground running, figuratively and literally – we recently got a treadmill desk for the office! You love to drill down into the nitty-gritty of a complex technical issue until you pinpoint exactly what’s causing it – no problem left unsolved! You’ve got a good sense of humour – feel free to tell us your most groan-worthy G-rated joke in your job application for bonus points.

You’ve got: 

  • 3-5 years experience working in an IT admin role
  • A diploma or degree in Information Technology or related field
  • Experience managing DR infrastructure with Veeam or equivalent
  • Experience with managing and troubleshooting network infrastructure
  • Strong understanding of DNS, DHCP, TCP/IP, Firewall, Switches & APs
  • Experience in management of Windows Server 2008/2012/2016/2019, Active Directory, Exchange/Office 365
  • Experience in management of Linux servers
  • Working knowledge of voice platforms (VoIP, PBX, Call Centres)
  • Ability to write documentation and processes
  • Excellent customer service and communication skills
  • Strong critical thinking and problem-solving skills

Your responsibilities will include: 

  • Management and maintenance of servers, workstations, and infrastructure
  • Providing second-tier technical support to our customers
  • Providing IT support to our team members
  • Working closely with the development team to identify bugs
  • Maintaining an enthusiastic and dedicated approach to understanding customers’ needs 

Meet the Team!

Angie has a Question of the Week for every staff meeting and a GIF for every Slack chat. She keeps our customers’ needs at the forefront by making sure the ticket and phone queue keeps movin’ and any escalated concerns are followed up with. She manages the team and keeps everyone in the loop about trends, bugs, and patterns we’re seeing in support. Most importantly, she does our office Costco runs! She’s also always up to date on her reality TV – so if you’re a fan of The Bachelor, that’s a bonus 💍🌹 

Bailey is our recent addition to the team and she’s already crushin’ it! Which, in the context of our Customer Success team, means diving right in to help our customers on the phone and by email whenever they have a question or run into an issue. We asked Bailey to describe herself in a few words and she said “wine, coffee, and true crime.” We then made a mental note not to catch her on a bad day 😛 During the pandemic, Bailey’s been keeping busy taking walks every day – she’s up to around 100km/week (putting the rest of us who haven’t gotten off the couch in months to shame 🙈). 

Matt is a support rock star, spending his days answering tickets and walking our members through their questions on (sometimes very long…) phone calls. He’s also part of our onboarding team, where he helps new users get their accounts set up and ready to goOutside of work, Matt enjoys travelling, trying new food (or just eating in general 😋), and long walks on the beach. Want to hear some really cool stories? Ask him about his time spent teaching in Japan! 

Natalie is the go-to for beep-boop music and spoiling Marvel movies. As the office Zillenial, she always brings a different perspective to our lunchtime chats (which is our way of saying some of us are too old to understand any of her references 😭). During the workday, she’s busy going above and beyond to help our members over the phoneemail, or on Zoom while onboarding new users. Natalie’s currently enjoying the perks of the Atlantic bubble, working remotely from New Brunswick for the time being. 

Todd has the perfect dad joke for every conversation and the best track record on Untappd. He’s also the guy who handles our escalated technical support tickets and IT. If you ask the support team what that means, he’s the one who saves them when a really complex technical question or bug comes up. If you ask the developers, he’s the one who brings them bad news and problems all the time. Todd recently celebrated 5 years at Port 443! 🎉 


Other Perks/Benefits

  • Free snacks and coffee – are you Team Hazelnut or Team Regular? 
  • Last Friday of the Month Lunch – vote for a new lunch spot every month, and watch as your coworkers get in heated debates over burritos vs burgers 
  • Company social events throughout the year – significant others welcome! 
  • Cool company swag when we reach milestones – check our IG to see some of our past swag 
  • Comprehensive health benefits plan – now you can stop putting off that dentist appointment! 

When you come to work at Port 443, you’re joining a team that balances innovation, excellence, and fun. If this sounds like the perfect fit for you, we want to hear why! To let us know why this job posting speaks to you and what you can bring to the table, send your cover letter, resume, and favourite donut flavour to