Lead Product Designer

Jobless; Toronto; Hybrid; CAD 160,000 - 190,000; Full time

Benefits offered by this job

30 days PTO annually

Health, dental and wellness benefits

Tech allowance

Pregnancy and parental leave

Employee ownership

Job summary

Jobless in Toronto is seeking a Lead Product Designer to own the home management experience, shaping features that help homeowners move from reactive to proactive care. You will lead design in the product trio with product and engineering leads, identifying problems worth solving and driving outcomes.

AI is central to the work, turning property data into intelligent plans and enabling hands-on use of AI tools in practice.

Qualifications

• Lead end-to-end product design work from discovery through shipped product.
• Background in innovation or R&D style design work with 0-1 product hypotheses validated.
• Ability to design complex, data-rich systems that feel simple and trustworthy.
• Strong visual and interaction design craft; proficient with modern design tools.

Responsibilities

• Own the design of the home management experience end to end, guiding homeowners from reactive to proactive care of their homes.
• 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.
• Design AI-assisted features turning data into personalized experiences homeowners trust.
• Take features from concept to high-fidelity design and contribute to the design system.
• Use AI tools hands-on and elevate how design uses AI across the product.
• Communicate insights and design rationale clearly to align product, engineering, and leadership.

Skills

End-to-end product design

AI-powered features

Design systems

Prototyping

Team collaboration

User research

Tools

Figma

Job description

BUILD SOMETHING YOUR NEIGHBOURS WILL LOVE

We’re building Toronto’s dedicated platform for home management to empower the city’s homeowners and to better connect our neighbours and the local Pros they trust.

Our focus is purely on the GTA market right now. We build our property base one street at a time, and our marketplaces one neighbourhood at a time. We’re a local tech company in every sense of the word. We start with integrity, neighbourhood values, and competitive craftsmanship, and we build our business on neighbourhood trust.

We believe in holistic solutions to consumer problems. We believe in high-trust hyperlocal communities. We believe in low commission marketplaces that the best Pros can actually say yes to. And we believe that 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. We believe that it’s good business to care. We believe that this problem space deserves a form of digital transformation that the people and Pros of the markets we serve can trust and invest in, in Toronto and beyond.

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 SALARY BAND

$160,000 - $190,000

ROLE OVERVIEW We’re hiring a Lead Product Designer to own the design of our home management experience, the suite of features that helps homeowners move from reactive to proactive care of their homes.

We're building on the success of features like our garbage and recycling reminders with personalized maintenance plans, smart tasks, and tools for managing home inventory, property information, and proactive repair and renovation planning.

This is a senior individual contributor role reporting to the Director of Design. You'll be the design lead in the product trio for the Holistic Home Management team, partnering closely with the product lead and engineering team lead to identify the problems worth solving and sharing accountability for the outcomes this team delivers. We're looking for a designer with deep empathy for homeowners who can take broad, conceptual ideas and turn them into highly impactful designs, making sure every touchpoint of the experience is considered, crafted, and worthy of our users' trust.

AI is key to the work in two ways. The vision for these features is AI-assisted, turning property data into intelligent plans and recommendations. We also expect you to use AI tools hands‑on in your own practice. This role is a strong fit for a designer with an innovation practice or R&D background who is energized by working at the intersection of product viability, feasibility and desirability.

WHAT YOU WILL BE DOING

• Own the design of the home management experience end to end, guiding homeowners from reactive to proactive care of their homes
• 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

• 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

NICE TO HAVE

• 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

THIS IS A GOOD FIT FOR YOU IF…

• You’re mission‑driven and looking to solve the mission’s hardest problems.
• You’re at a point in your life and your career where you want to tackle a uniquely demanding job to produce meaningful impact.
• You’re keen to work in a hybrid role where you’re in office with a team 3 days a week. You have flexibility to have further in office presence collaboration with leadership or other hands‑on work as required.
• You show up like an owner.
  

TEAM VALUES

Integrity – 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 customers’ 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 BENEFITS

We 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 OWNERSHIP:

We’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. We want people who value ownership in the scope of their role, and in the equity they hold in the company to help us make something meaningful happen.