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 Lead Product Designer to help guide and mentor our already awesome team and make our products genuinely easier and better to use. This is a current role within an established team of 4 designers that’s been overseen by a technical leader Bless his heart, he’s done a great job, but you can probably already tell why we need an actual product design expert in here ASAP. This isn’t a role where someone hands you a perfectly defined feature, you make some nice-looking screens, and everyone calls it a day.



We need someone who actually likes the messy part. You’ll dig into real customer problems, ask a lot of questions, challenge assumptions, and help us figure out the right thing to build before jumping into Figma. You’ll also lead and develop the Product Design team through coaching, feedback, 1:1s, and design reviews. This is very much a player-coach role. You’ll own design work yourself while helping the team become stronger, more confident, and more independent over time. Our products have been around for 13+ years, so there’s a lot to learn. We don’t expect you to know it all on day one, but we do want someone who’s genuinely curious and wants to become an expert in how our customers run their businesses. Basically, we need someone who can take a complicated problem and help us get to a solution that makes everyone go, “Oh. Duh. Obviously it should work that way.” About You

Now let’s talk about you. First of all, you have to be fun and have a sense of humour, or else you probably won’t survive here. Now that that’s out of the way, let’s talk product design. You’re a problem solver first and a designer second. You don’t immediately open Figma when someone tells you there’s a problem. You ask questions. Probably a lot of them. You want to understand what’s actually going wrong, who it affects, and whether the thing everyone thinks we should build is even the right solution.



You can zoom out and understand the bigger workflow, but also zoom in and spot the tiny interaction that’s going to confuse the hell out of someone. You know good product design isn’t just about making something clean or pretty. It has to make sense. You’re confident enough to challenge ideas, including ones coming from leadership, and thoughtful enough to explain why. You also know how to coach other designers without just taking over and fixing everything yourself. You’re curious, practical, thoughtful, and probably a little obsessive about why things work the way they do. Most importantly, you genuinely care about building useful software for real people, not just making nice portfolio shots. What You Bring

8+ years of product design experience, ideally working on SaaS or other complex software products Strong experience owning product problems from discovery through to final design and implementation Experience leading, mentoring, and coaching other product designers into stronger, more independent problem solvers Excellent UX and interaction design skills, with a strong understanding of complex workflows, information architecture, states, and edge cases Strong product thinking and the ability to look beyond a requested feature to understand the actual problem and outcome we’re trying to achieve The ability to take an ambiguous problem, ask the right questions, align different perspectives, and create a clear path forward Experience with customer research, usability testing, interviews, and other forms of product discovery The confidence to challenge assumptions, explain your thinking, and give thoughtful pushback when something doesn’t make sense Strong visual design fundamentals and attention to detail, without prioritizing aesthetics

📌 Product Design Lead (Winnipeg)
🏢 Port 443
📍 Winnipeg