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.

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 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’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 new 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.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.

You’ll own design work yourself while helping the team become stronger, more confident, and more independent over time.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. Now that that’s out of the way, let’s talk product design.You don’t immediately open Figma when someone tells you there’s a problem. You know good product design isn’t just about making something clean or pretty.

Most importantly,



you genuinely care about building useful software for real people, not just making nice portfolio shots.8+ years of product design experience, ideally working on SaaS or other complex software productsStrong experience owning product problems from discovery through to final design and implementationExperience leading, mentoring, and coaching other product designers into stronger, more independent problem solversExcellent UX and interaction design skills, with a strong understanding of complex workflows, information architecture, states, and edge casesStrong product thinking and the ability to look beyond a requested feature to understand the actual problem and outcome we’re trying to achieveThe ability to take an ambiguous problem, ask the right questions, align different perspectives, and create a clear path forwardExperience with customer research, usability testing, interviews, and other forms of product discoveryThe confidence to challenge assumptions, explain your thinking, and give thoughtful pushback when something doesn’t make senseStrong visual design fundamentals and attention to detail, without prioritizing aesthetics over usabilityA self-starter mindset, solid ownership, adaptability, and genuine curiosity to dig into unfamiliar problems and learn quicklySaaS experience is strongly preferred, but if you don’t have it and still feel like you’d be a great addition to the team, apply anyway!Lead the day-to-day product design work across our SaaS productsTake ownership of complex customer and product problems from the early “what the hell should we do here?” stage through to final design and implementationWork closely with Product, Development, Support, QA, and leadership to understand problems, constraints, and downstream impacts before jumping into solutionsTalk to customers, review feedback,



and build a deep understanding of how they actually use our products and run their businessesExplore different solutions, challenge assumptions, and help define what a successful outcome should actually look likeCreate user flows, wireframes, prototypes, and polished product designs that make complicated things feel simpleThink through edge cases, permissions, different user types, error states, and all the less glamorous stuff that makes software actually work wellMentor and coach our designers, give thoughtful feedback, and help raise the quality bar across the teamHelp create patterns and principles that keep our products consistent and easier to evolve over timeChallenge ideas when needed, bring better ones to the table, and help us make smarter product decisionsMeet the Team! is our Tech Team Lead and the guy who’s been helping lead the Product Design team. He’s done a excellent job... but he’s a technical guy and wants to get back to all the nerdy stuff. He’s also a big Leafs fan and still hopes to see them play in a Stanley Cup game one day.is our Project Manager and basically our product encyclopedia after 10 years of being here.

He’s also got dad jokes for days, and when he’s not at work, you can find him on the dodgeball court punishing other people for his stress.Probably because he used to be a literal model travelling the world. He also loves working on boats.She also loves to travel and just got back from a trip to Europe with her family. is our resident customer expert and newest member of the Product Design team after spending years in Customer Success and QA. When he’s not helping make our products better, he’s probably at a Ticats game in his custom leather vest. is also fresh to the team after starting in Customer Success while going to school for Interaction Design.

He’s got a great eye for design and is very into coffee, gaming, and manga. 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.Comprehensive health benefits plan + health spending account go ahead and book that massage.

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