Customer Success Specialist

On-site: Burlington, ON

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 people person (don’t worry, we also hate that phrase and we promise not to use it again). 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 have a treadmill desk at the office! You’re a strong communicator that can explain some complex invoicing/accounting concepts with simplicity and clarity. You’ve got an eye for detail, so you’ll spot that typo and fix it before you hit send. 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 😂 (And you don’t mind that we still use the 😂 emoji even though apparently it’s not cool anymore!) 

You’ve got: 

  • 2+ years experience working as a customer success specialist
  • Technical knowledge – you must be able to troubleshoot, investigate, and think outside the box (brownie points if you have a basic understanding of HTML and CSS)
  • Exceptional written and verbal communication skills that engage our customers
  • A positive customer-centric mindset
  • An abundance of patience and empathy
  • Ideas! We want someone who’s excited to share their thoughts and suggestions with the team

Your responsibilities will include: 

  • Communicating with customers by telephone and email (so if you hate talking on the phone, this probably isn’t the job for you…)
  • Holding 1-on-1 onboarding sessions as well as product demos for the new members
  • Recording all incoming feedback and responding to customer issues in a timely fashion
  • Maintaining an enthusiastic and dedicated approach to understanding customers’ needs 
  • Educating customers on the full value of our products and services  
  • Serving as the voice of the customer and providing internal feedback on how we can better serve them
  • Working closely with the development team to identify bugs and track feature requests 
  • Travelling to exhibit at trade shows (up to 10% travel may be required) 

Meet the Team!

Bailey is our awesome Senior Customer Support Specialist who goes above and beyond to help both our customers and the team whenever they have a question or run into an issue! She’s also the go-to for dissecting the latest episode of whatever reality show is out at the time! 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 😛 

Chris is an artistic soul, working through creative solutions to our customers’ technical issues by day, and creating beautiful paintings and sculptures by night! 🎨 He’s always going out of his way to be as helpful and friendly as he can (which comes naturally to him!), so it’s no wonder our customers love when they get him on the phone or get to talk to him at a trade show. If you want to live vicariously through him, ask him about his amazing trip to Cuba! 

Diana is our outgoing Customer Success Specialist with an infectious laugh! Whether over the phone, in a ticket, on an onboarding call, or giving a virtual demo, she loves to help our customers understand our products on a deeper level and make sure they’re set up for success. She lifts up our spirits simply by being the awesome person she is… and by sharing pictures of her adorable corgi! 🐾  

Jameela is another of our Customer Success Specialists, whose joy brings positive energy & good vibes to the office every day! Her background in teaching means she’s got the perfect skills to help educate our members on any tech issues they run into and be incredibly patient on the phone when they have lots (and lots and lots…) of follow-up questions! One thing on Jameela’s bucket list is to open up a boutique dessert shop. We’re happy to be taste-testers for you, Jameela! 🧁 

Larisa is our Customer Success Manager who does everything she can to make sure we’re focused on our customers as people, not as numbers. She always goes out of her way to make everyone at the company feel appreciated. Is that by bribing us with chocolate? Maybe. But is that really such a bad thing? 🍫 In her spare time she’ll be found spending time with her family, going to a Ticats game, or spending time with the fam at a Ticats game! 

Mike is our resident donut chauffeur, Ticats enthusiast, and office vegan (even though he’s not a vegan). As the Senior Technical Support Specialist, he uses his extensive knowledge of our products and our customers to troubleshoot technical problems & investigate issues like no other! In his spare time, you can catch him watching everything from MMA to stand-up comedy to Drag Race 📺 

Pedia is our Customer Onboarding Specialist who always makes sure to put the customer’s needs first. She’s a pro at helping our new members learn about our products and get their accounts set up just how they need to be. In fact, she’s so good at it that someone attending a group demo once thought she was AI-generated! Pedia’s also usually the one who gets the coffee brewing in the morning, so we’d be lost (and much more tired) without her ☕ 


Other Perks/Benefits 

  • Free snacks and coffee – are you Team Hazelnut or Team Regular?  
  • 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