Lead Product Designer

BUILD SOMETHING YOUR NEIGHBOURS WILL LOVEWe’re building home management for GTA homeowners, and a better way for neighbours and the local Pros they trust to be useful to each other.
Our focus is the GTA, and only the GTA for now. We grow one neighbourhood at a time. We’re a local tech company in every sense of the word, and we start with integrity and the belief that good work matters.
We believe homeowners should have everything their home needs in one place, and that neighbourhoods work best when trust runs high and stays local. Commissions should be small and charged only on completed work, so the best Pros can actually say yes. Tech companies should go to work for the locally loved Pros of the GTA, rather than trying to get those Pros to effectively work for the tech company.
If this resonates with you and you’re at a point in your career and your life where you want to do something uniquely difficult for a meaningful outcome, you’ve found your next home.
ROLE OVERVIEWQuartermaster is building a utility-scale product that helps homeowners manage their homes, from DIY maintenance to finding trusted Pros through referrals from friends and neighbours. Today, separate teams focus on home management, referrals, and Pro discovery, booking, and payment. Your team will work across all of them in order to get maintenance Pros to invite their book of business to Quartermaster.
This is a senior individual contributor role reporting to the Head of Product. As design lead in the product trio for the Win Maintenance team, you'll partner closely with the product and tech leads to decide which problems are worth solving, and you'll share accountability for the outcomes the team delivers.
We're looking for a designer with deep empathy for homeowners and Pros who can turn broad, conceptual ideas into high-impact designs. You'll make sure every touchpoint is considered, crafted, and worthy of our users' trust, whether that's a homeowner reviewing a plan for their home or a Pro deciding to bring their customers on board.
AI shapes this work in two ways. First, the product vision is AI-assisted: turning property data into intelligent plans and recommendations. Second, we expect you to use AI tools hands‑on in your own design practice.
This role is a strong fit if you thrive in ambiguity, have 0-to-1 product experience, and are energized by the intersection of viability, feasibility, and desirability.
WHAT YOU’LL BE DOING
Own the design of the win maintenance experience end to end. Allow maintenance Pros to run all of their business through Quartermaster, and make it easy for Homeowners to book Pros for their maintenance needs.
You will be collaborating with with other teams in order to deliver value to your customers on both the Homeowner and Pro sides of the platform.
Operate as the design lead in the product trio, partnering with the product lead and engineering team lead to define outcomes and deliver against them
Identify product opportunities through research, and validate hypotheses with prototypes, experiments, and user feedback before we invest in building
Design AI-assisted features that turn property, behavioral and environmental data into personalized experiences homeowners genuinely trust
Take features from early concept through high‑fidelity design, contributing to the Quartermaster design system as you ship
Use AI tools hands‑on in your design practice, and help raise the bar for how design at Quartermaster works with AI
Communicate insights and design rationale clearly, building alignment with product, engineering, and leadership
WHAT YOU BRING TO THE TABLE
A track record of leading end-to-end product design work as a senior individual contributor, from discovery through shipped product
A background in innovation practice or R&D style design work. You've taken 0-1 product hypotheses from research through validation, looking at problems from both a human‑centred and systems point of view
The ability to design complex, data‑rich systems that feel simple, personal, and trustworthy
Strong visual and interaction design craft, with fluency in modern design and prototyping tools
A genuine interest in AI, both as a subject of design and as a tool in your own practice. Direct experience designing AI‑powered features is a plus, not a requirement
Comfort operating in ambiguity and complementary communication skills that builds trust with product, engineering, and executive audiences
Excellence in identifying trade‑offs and opportunities for improvement, and good judgment in navigating them - both in products themselves and in the way your team works on them
Experience with experimentation, incremental delivery and tight feedback loops, where user behaviour plays a major role in shaping the evolution of the product
Ability to keep the big picture in mind while working in the weeds - and pay close attention to low‑level details while working on the big picture
Ability to bridge divides and create shared understanding among engineers, product managers, designers and customer‑facing teams
IN A PERFECT WORLD, YOU HAVE EXPERIENCE THE FOLLOWING
Experience designing AI‑powered product features
Comfort using AI tools hands‑on in your design process
Comfort and familiarity programming in web technologies
Experience designing for a marketplace or two‑sided platform
ROLE SALARY BAND$150,000 - $190,000
LOCATIONWe believe that in‑person work builds a level of connection and shared understanding that fully‑remote work cannot achieve.
This role requires you to work at our office every Monday, every Thursday and every second Tuesday. Reasonable exceptions are made when life happens, but these should be infrequent.
If you are not already located in Toronto or one of its nearby suburbs, we will only be able to consider your application if you already have concrete plans to relocate to the Toronto area.
OUR VALUESIntegrity – We prioritize integrity over comfort, convenience, and the short‑cuts of success that drive metrics but undermine trust.
Trust – We cannot win unless we win on trust. Trust is hard to earn and easy to lose. We need to be built for it in our DNA.
Competitiveness – We believe that competitiveness is a critical complement to integrity and trust. If we’re not our customer’s best choice, then we’re wasting their time. We believe in the power of healthy competitive markets, and we believe we need to be uniquely competitive to win in this space. We have too much respect for the other players in this space to expect things to be easy. That’s a good thing.
Empowerment – Any win we achieve needs to be first and foremost a win that we deliver to others, starting with our customers, and their long term best interests.
VACATION AND BENEFITSWe know the power it takes to be successful in a challenging mission and we want to ensure our team is rested and ready to go.
We offer 30 days of PTO annually, which can be used for vacation, personal days, or illness. Five of these days are designated as company‑wide closures around the start and end of the year.
In addition, our benefits plan covers health, dental and wellness to add that extra pep in our step, and help us sleep at night.
We have a tech allowance benefit to help set you up for work.
We have pregnancy and parental leave policies, and we’re ready to support your family’s next stage of growth.
EMPLOYEE OWNERSHIPWe’re a team on a mission. We expect a high degree of ownership from each other and we pair that with higher‑than‑usual employee ownership in the company.
A NOTE ON HUMAN BEINGSWe believe that meaning is created between human beings. This job description was written by a human, and every resume will be reviewed by a human.
OUR INTERVIEW PROCESS
Intro and initial screen (60 min)
Portfolio review and craft assessment (60 min)
Cross-functional (60 min)
Mission and Culture fit (60 minutes)
Notes
Rounds 2, 3, and 4 may be run in slightly different order based on availability on both sides
Round 2, 3 or 4 may be stacked back to back in order to reduce total interview cycle time
At least 1 of rounds 2, 3, or 4 will be run in person at our Downtown Toronto office
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