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Quartermaster

Lead Product Designer

Quartermaster

. Own the design of the win maintenance experience end to end .

Posted 11/11/2026full-timeToronto • CanadaSenior💰 CA$150,000 - CA$190,000 per yearWebsite

Core Competencies

Role fit
Core Competencies

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Demonstrates expertise in end-to-end product design, focusing on AI-assisted features and data-rich systems that enhance user experience. Proficient in collaboration across teams to drive innovation and validate product hypotheses through research and user feedback.

Highest-signal resume keywords
End-To-End Product DesignAI-Assisted Feature DesignVisual And Interaction DesignPrototyping Tools FluencyData-Rich System Design

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills
End-To-End Product DesignAI-Assisted Feature DesignVisual DesignInteraction DesignPrototypingData-Rich System DesignExperimentationIncremental DeliveryWeb Technologies ProgrammingMarketplace Design
Soft Skills
CollaborationCommunicationComfort Operating In AmbiguityCreating Shared Understanding
Tools & Technologies
Design ToolsPrototyping ToolsAI Tools
Industry Keywords
Innovation PracticeR&D-Style DesignTwo-Sided Platform

About the role

Key responsibilities & impact
  • Own the design of the win maintenance experience end to end
  • Enable maintenance Pros to run all of their business through Quartermaster
  • Make it easy for homeowners to book Pros for maintenance needs
  • Collaborate with other teams across the Homeowner and Pro sides of the platform
  • Operate as 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
  • Validate hypotheses with prototypes, experiments and user feedback before investing in development
  • Design AI-assisted features that turn property, behavioral and environmental data into personalized experiences homeowners trust
  • Take features from early concept through high-fidelity design
  • Contribute to the Quartermaster design system while shipping
  • Use AI tools hands-on in design practice and help improve how design works with AI at Quartermaster
  • Communicate insights and design rationale with product, engineering and leadership

Requirements

What you’ll need
  • Track record of leading end-to-end product design work as a senior individual contributor, from discovery through shipped product
  • Background in innovation practice or R&D-style design work
  • Experience taking 0-to-1 product hypotheses from research through validation
  • Ability to design complex, data-rich systems that feel simple, personal, and trustworthy
  • Strong visual and interaction design craft
  • Fluency in modern design and prototyping tools
  • Genuine interest in AI, both as a subject of design and as a tool in personal practice
  • Comfort operating in ambiguity
  • Experience with experimentation, incremental delivery and tight feedback loops
  • Ability to bridge divides and create shared understanding among engineers, product managers, designers and customer-facing teams
  • Experience designing AI-powered product features is a plus, not a requirement
  • Comfort and familiarity programming in web technologies is preferred
  • Experience designing for a marketplace or two-sided platform is preferred

Benefits

Comp & perks
  • 30 days of PTO annually, including vacation, personal days, or illness
  • Five company-wide closure days around the start and end of the year
  • Health, dental and wellness benefits
  • Tech allowance benefit
  • Pregnancy and parental leave policies
  • Higher-than-usual employee ownership in the company