Principal Product Designer

Dropbox; Saskatchewan; On-site; CAD 216,800 - 293,300; Full time

Job summary

Dropbox is seeking a Principal Designer to define the future of content activation for its customers. You will lead the design vision for Dropbox’s multi-product ecosystem, shaping strategy and execution across products and services.

You will mentor designers, raise craft standards, and translate emerging AI capabilities into simple, high-trust experiences. Collaborate with product, engineering, research, marketing, and design leadership to achieve impactful outcomes.

Qualifications

• 12+ years of product design experience leading complex, high-impact initiatives.
• Portfolio demonstrates Principal-level craft, product judgment, and ability to ship trusted experiences.
• Exceptional executional range from long-term strategy to detailed flows and prototypes.
• Proven ability to influence senior cross-functional partners and drive product direction.
• Ability to translate emerging AI capabilities into simple, elegant experiences.
• Collaborative leadership with mentoring and standards improvement.
• Experience designing end-to-end experiences across multiple products.
• Portfolio shows a deeply opinionated design sensibility visible in work.
• Ability to simplify complex systems into premium, obvious experiences.

Responsibilities

• Define and drive the design vision for Dropbox’s multi-product ecosystem.
• Design AI-powered experiences that feel like a trusted partner and accelerate decisions.
• Lead high-impact product areas from strategy through launch at scale.
• Set a high craft bar across interaction design, IA, systems thinking, prototyping, content, and visuals.
• Partner with Product, Engineering, Research, Marketing, and Design leadership to shape strategy and drive outcomes.
• Mentor designers, raise standards, improve critique, and help the team become AI-enabled.

Skills

Principal craft

Systems thinking

Customer empathy

Storytelling for alignment

Mentoring designers

Cross-functional collaboration

End-to-end design

Job description

Dropbox is a Virtual First company. For this role, we are currently only authorized to hire candidates from the following provinces: Alberta, British Columbia, Ontario, and Saskatchewan.

Role Description

Dropbox’s Design team is looking for a Principal Designer to help define the future of content activation for Dropbox customers. In this role, you will help lead the design vision and execution for Dropbox’s portfolio of products and services.

Responsibilities

• Define and drive the design vision for Dropbox’s broader multi-product ecosystem that helps customers find, understand, activate, and act on content already living in Dropbox.
• Design AI-powered experiences that make customers sharper and more effective without replacing their judgment. Ensure AI feels like a trusted partner: reducing friction, surfacing what matters, accelerating decisions, and keeping customers in control.
• Lead ambiguous, high-impact product areas from strategic framing through execution, translating emerging AI capabilities into simple, elegant, high-trust experiences that feel powerful without becoming clunky, noisy, or difficult to use.
• Set an exceptionally high craft bar across interaction design, information architecture, systems thinking, prototyping, content, visual quality, and implementation. Make the product feel precise, coherent, and unmistakably Dropbox.
• Partner deeply with Product, Engineering, Research, Marketing, and Design leadership to shape strategy, prioritize the highest-impact opportunities, align teams, and drive outcomes with urgency and quality.
• Raise the bar for the design organization by mentoring designers, improving critique, modeling excellent AI product design, and helping the team become more AI-enabled in how they explore, prototype, evaluate, and ship work.

Requirements

• 12+ years of product design experience, with a strong track record leading complex, ambiguous, high-impact product initiatives from vision through launch at scale.
• A portfolio demonstrating Principal-level craft, product judgment, systems thinking, customer empathy, and the ability to ship experiences that customers understand, trust, and love.
• Exceptional executional range, with the ability to move fluidly from long-term strategy and narrative to detailed flows, interaction models, prototypes, edge cases, content, and implementation quality.
• Proven ability to influence senior cross-functional partners, create alignment through clear storytelling, and drive product direction in fast-moving, ambiguous environments.
• Strong ability to translate emerging capabilities into simple, useful, intuitive product experiences that reduce friction, preserve customer agency, and help people get meaningful work done.
• A collaborative, low-ego leadership style, with a track record of mentoring designers, raising standards, improving critique, and helping teams produce better work than they could have produced on their own.
• Experience designing end-to-end experiences across multiple products, surfaces, or platforms, with a strong ability to create coherence across complex user journeys.
• A portfolio that shows a deeply opinionated design sensibility, where the candidate’s taste, principles, and product philosophy are visible in the work itself.
• A demonstrated ability to simplify complex systems, workflows, or mental models into experiences that feel premium, obvious, and easy to use.

Preferred Qualifications

• Deep experience designing customer-facing products in emerging or complex domains such as AI, search, knowledge work, productivity, collaboration, enterprise software, or multi-product ecosystems.
• Experience designing or simplifying agentic experiences, agent management, automation, orchestration, permissions, delegation, or similarly complex product metaphors where users need clarity, control, and trust.
• A strong point of view on how AI can augment human judgment, activate customer content, reduce busywork, and make customers sharper without making the experience feel clunky, opaque, or over-automated.
• A strong point of view on design craft in the AI era, including how designers should use AI to increase creativity, speed, quality, and customer understanding.

Compensation

Canada Pay Range: $216,800—$293,300 CAD (expected annual salary/OTE)

All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock in the form of Restricted Stock Units (RSUs).

EEO Statement

Dropbox is an equal opportunity employer. We are a welcoming place for everyone, and we do our best to make sure all people feel supported and connected at work.