Customer Success Specialist

About Us

We’re a small but mighty software company in Burlington, Ontario. We’re 100% bootstrapped, profitable, and have been building software for over 13 years. Our three flagship products, My Music Staff, TutorBird, and AthletaDesk, help private music teachers, tutors, and personal trainers run their businesses more smoothly.

We’re also a fully in-office company, and we like it that way. That said, we’re still human. Flexibility is there when it’s needed.

We’re not your typical corporate company that leaves you feeling dead on the inside by Wednesday. Our company mission is literally building a place we want to work. We like being a small team. We don’t want to be a giant company where people don’t even know each other’s names.

Being small also means people can wear different hats, try new things, and actually see the impact of their work. We’re definitely a work hard, play hard kind of team. We care a lot about building useful products, listening to our customers, and showing up like actual humans. That matters to us in how we support our customers and how we treat each other internally.

Other things that matter to us include: donuts, coffee, team lunches, going to Wonderland together, and Mario Kart. We take that sh*t seriously.

About the Role

Okay, back to business.

We're looking for a Customer Success Specialist to join our awesome team! You'll help customers who use My Music Staff, TutorBird, and AthletaDesk to run their businesses.

We're big believers in humans helping humans. While a lot of companies are moving away from human support, we're pretty proud of ours. Our customers appreciate being able to talk to a real person who actually listens, understands their problem, and helps them figure things out. Sometimes that means answering a simple question. Other times, it means digging through invoices, payments, schedules, and settings to figure out why something isn't adding up. You'll need to put on your detective hat pretty often around here. 🕵️

You'll spend your days helping customers over phone, email, and video calls, troubleshooting problems, and helping people get the most out of our software. Our products are pretty complex, and there's a lot to learn. We don't expect you to know everything on day one. We'll teach you the software, but you'll need to bring the problem-solving skills!

About You

First things first, you're a people person. (Ugh, we know. We hate that phrase too.) You're friendly, patient, and genuinely enjoy helping people. But you're also a really good problem solver. You're the type of person who needs to understand why something works the way it does, not just memorize the steps.

You're comfortable with numbers, can wrap your head around accounting concepts, and have a knack for figuring things out when they don't immediately make sense. When something doesn't add up, you don't just shrug your shoulders. You dig in until you've figured it out. You can think on your feet, ask good questions, and explain complicated things in a way that actually makes sense.

And of course, you've got a good sense of humour. We take our work seriously, but ourselves? Not so much.

What You Bring

• Strong critical thinking and problem-solving skills. You can connect the dots and work through problems without needing someone to hold your hand.
• Confidence with math and basic accounting concepts. You'll be dealing with invoices, payments, balances, and calculations pretty regularly.
• Excellent written and verbal communication skills. You can make complicated things sound simple.
• A natural curiosity and the ability to pick up new software and concepts quickly.
• Patience, empathy, and a genuinely helpful attitude, even when things get frustrating.
• Great attention to detail. You notice when something doesn't look quite right.
• Customer service experience is a plus, and SaaS experience is even better!

What You'll Do

• Help customers by phone, email, and video calls. (If you hate talking on the phone, this probably isn't the job for you 😉)
• Investigate and troubleshoot customer issues, including some pretty complex scheduling, invoicing, and payment scenarios.
• Figure out what's actually going wrong, even when customers aren't quite sure how to explain it.
• Teach customers how to use our software and make their day-to-day lives a little easier.
• Document customer issues, feedback, and feature requests so nothing falls through the cracks.
• Work with our team to identify bugs, share customer feedback, and help make our products better.

Meet the Team!

Bailey is our team lead and is one of those people who actually handwrites everything in her planner. She’s powered by Diet Coke, reality TV, and whatever her book club is reading next. 📒

Jameela brings good vibes and teacher-level patience to every conversation. She’s also got a dessert shop on her bucket list, and we all want to be taste testers. 🧁

Ziad is calm, creative, and somehow makes the technical stuff feel easy. He’s either behind a camera, cooking something good, or planning his next trip. 🎥

Olivia is all about the details, both in customer support and in her art. She paints with acrylics, makes digital illustrations, and designs custom stickers for fragrance brands. 🎨

Nadiyah is dreaming about Jamaica and manifesting Paris like it’s already booked. She also firmly believes tacos count as a daily essential. 🌮

Aaron is an audiophile at heart. He dreams of opening a coffee shop one day and will never say no to poutine. ☕

Charliene is a travel loving foodie. She’s hoping to backpack across Asia and is always down for sushi. 🍣

Kaden is chill and always up for a good chat. After living in China for four years teaching English, he’s still dreaming about fresh seafood in Weihai, hotpot for life, and a future trip to Japan. ✈️

Sameer takes fitness and shawarma equally seriously. He's a personal trainer, a second-degree black belt, and he has an actual spreadsheet ranking the best shawarma spots around. 🥙

Other Perks/Benefits

• Free snacks and coffee ☕ because we know the way to your heart.
• Fun company social events throughout the year 🎉 and yes, significant others are always welcome.
• Cool company swag when we hit milestones 👕 check out our IG to see some of our past goodies.
• Comprehensive health benefits plan + health spending account 🏥 go ahead and book that massage. You’ve earned it.
• GRSP with company match 💰 a little something for future you, too.

Did you read all that and still think this sounds like your kind of place? We’d love to hear from you. Submit your cover letter and resume!

P.S. A real human reads every submission, so don’t be shy. Let your personality shine!!

Please note that while we appreciate every application, we may not be able to respond to all applicants. If you make it to the next round, we’ll be in touch.