Director of Design

Toronto /
Design /
Full time
Drop is a rewards company on a mission to level-up the way consumers shop. Drop builds a personalized rewards experience from over 300 partner brands. To date, Drop has over 3 million users and has rewarded over $20 million to consumers.

Headquartered in Toronto, with an office in New York, Drop is backed by world-class investors including NEA, HOF, Royal Bank of Canada, Sierra Ventures, and White Star Capital. 

Visit joindrop.com or follow the company at @joindrop on Twitter and Instagram.

The Role

    • We're looking for a passionate Director of Design to hire, mentor, and develop the design team so that they can produce great work which solve consumer problems in balance with business needs
    • Work closely and collaboratively with the leadership team to develop and evangelize a product vision and roadmap by helping to define the why and how behind both the long-term strategy and short-term tactical initiatives
    • Advocate for data - informed product and design decisions through continuous experimentation, usability testing, and member insights
    • Identify, prioritize problems and major opportunities across the product, and work with cross-functional teams in delivering solutions against those problems

What kinds of challenges will the Director of Design be working on at Drop?

    • Exceptional design craft that ensures a high standard for all product deliverables
    • Understand consumer problems through insights derived from user research, user experiences and internal stakeholders to shape requirements, features and end product 
    • Navigate ambiguity, create clarity, and drive design excellence throughout the organization
    • Understanding tactical and strategic goals of the company and how design works cross-functionally to deliver impact
    • Streamline and systematize processes across teams to ensure handoff or signoff of designs, deliverables, and assets happens as efficiently as possible
    • Work with product leadership to develop product vision, create product plans and roadmaps
    • Guide the work of talented product designers and visual designers by leading and/or facilitating design team critiques, discussions, sprints, etc. in a supportive environment 

What you bring to the table

    • 5+ years of proven experience in leading a design team
    • Strong communication skills with an ability to synthesize complex situations and build a clear narrative for C-level executives
    • Experience in releasing features that impact user growth and retention
    • Experience in collaborating with product managers, developers, other internal stakeholders, and customers
    • Able to empathize with the user and use data to inform design decisions with prioritization in mind
    • Demonstrable success in creating, launching, scaling, and maintaining digital products
    • Deep understanding of the design process and best practices, and proven ability to define and improve a team’s design practices
    • Able to focus on details and think strategically at the same time
    • A proven track record of hiring diverse teams, developing talent, and leading with positivity and inspiration
    • A comprehensive design thinking and user research toolkit e.g. Jobs to be done framework, “how might we” questions, clickthrough prototypes, interaction flows, etc.
    • Have an entrepreneurial mindset: you aren’t afraid to roll up your sleeves, thrive in controlled chaos, and getting things done
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At Drop, we're committed to providing an enjoyable and meaningful environment for every member of our team. We operate under a flat structure with minimal hierarchy where everyone’s opinion is valued equally. We are looking for team members with an entrepreneurial mindset who will thrive in a fast-paced and rewarding environment.


Drop Technologies, Inc. is proud to be a diverse and equal opportunity employer and as such does not discriminate on the basis of race, colour, religion, sex, national origins, age, sexual orientation, disability or any other characteristic protected by applicable laws. Selection decisions are solely based on job-related factors.