Product Design Lead

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 RoleOkay, 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 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.
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 YouNow 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 over usability
A self-starter mindset, strong ownership, adaptability, and genuine curiosity to dig into unfamiliar problems and learn quickly
SaaS 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!
What You’ll Do
Lead the day-to-day product design work across our SaaS products
Take ownership of complex customer and product problems from the early “what the hell should we do here?” stage through to final design and implementation
Work closely with Product, Development, Support, QA, and leadership to understand problems, constraints, and downstream impacts before jumping into solutions
Talk to customers, review feedback, and build a deep understanding of how they actually use our products and run their businesses
Explore different solutions, challenge assumptions, and help define what a successful outcome should actually look like
Create user flows, wireframes, prototypes, and polished product designs that make complicated things feel simple
Think through edge cases, permissions, different user types, error states, and all the less glamorous stuff that makes software actually work well
Mentor and coach our designers, give thoughtful feedback, and help raise the quality bar across the team
Help create patterns and principles that keep our products consistent and easier to evolve over time
Challenge ideas when needed, bring better ones to the table, and help us make smarter product decisions
Meet the Team!Vick
is our Tech Team Lead and the guy who’s been helping lead the Product Design team. He’s done a great 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.
Todd
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.
Dane
is one of our Intermediate Product Designers and is always cool, calm, and collected when working through problems. Probably because he used to be a literal model travelling the world. No biggie. He also loves working on boats.
Wedad
is our other Intermediate Product Designer. She’s small but mighty and her attention to detail is unmatched. She also loves to travel and just got back from a trip to Europe with her family. We’re all very jealous.
Mike
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. Yes, you read that right.
Richie
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. He’s a pretty cool guy.
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.
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.
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